Heterocyclic chemistry: 2 Five-membered heterocycles
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| Format: | Buch |
| Sprache: | English |
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Berlin [u.a.]
Springer
1999
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| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | X, 638 S. graph. Darst. |
| ISBN: | 3540652523 |
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MARC
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| 245 | 1 | 0 | |a Heterocyclic chemistry |n 2 |p Five-membered heterocycles |c R. R. Gupta ; M. Kumar ; V. Gupta |
| 264 | 1 | |a Berlin [u.a.] |b Springer |c 1999 | |
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| 700 | 1 | |a Kumar, Mahendra |d 1957- |e Verfasser |0 (DE-588)120453355 |4 aut | |
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| adam_text | CONTENTS CHAPTER 1. INTRODUCTION CHAPTER 2. FIVE-MEM BERED HETEROCYCIES
WITH ONE HETEROATOM CHAPTER 3. BENZO-FUSED FIVE-MEMBERED 181
HETEROCYCIES WITH ONE HETEROATOM CHAPTER 4. FIVE-MEMBERED HETEROCYCIES
WITH TWO HETEROATOMS 357 CHAPTER 5. FIVE-MEMBERED HETEROCYCIES WITH MORE
THAN TWO HETEROATOMS 487 CHAPTER 6. MESO-LONIC HETEROCYCIES SUBJECT
INDEX 579 627 4 HETEROCYCLIC CHEMISTRY 2 PYRROLES 33 2.1 GENERAL 33
2.1.1 EXTRACTION 33 2.1.2 EHRLICHTEST 34 2.2 SYNTHESIS 34 2.2.1
CYCLIZATION REACTIONS 34 2.2.1.1 (3 + 2) CYCLIZATION REACTIONS 34
2.2.1.1.1 REACTION OF A-AMINO KETONES OR 34 A-AMINO P-KETO ESTERS WITH
P-DIKETONES OR P-KETO ESTERS (KNORR PYRROLE SYNTHESIS) 2.2.1.1.2
REACTION OF A-AMINO KETONES WITH 36 ALKYNES 2.2.1.1.3 REACTION OF
P-AMINO-A,P-UNSATURATED 37 ESTERS WITH NITROALKENES 2.2.1.1.4 REACTION
OF A-DIKETONES WITH AMINES 37 2.2.1.2 (2 + 2+1) CYCLIZATION REACTIONS 38
2.2.1.2.1 REACTION OF P-KETO ESTERS WITH A-HALO 38 KETONES (HANTZSCH
PYRROLE SYNTHESIS) 2.2.1.2.2 REACTION OF ALDEHYDES OR KETONES 38 WITH
HYDRAZINE (PILOTY-ROBINSON PYRROLE SYNTHESIS) 2.2.1.2.3 REACTION OF
BENZOIN WITH BENZYL 38 ARYL KETONES 2.2.1.2.4 REACTION OF ALDEHYDES WITH
ALKYL 41 ISOCYANOACETATES 2.2.1.3 (4+1) CYCLIZATION REACTIONS 41
2.2.1.3.1 REACTION OF 1,4-DIKETONES WITH 41 AMMONIA OR AMMONIA
DERIVATIVES (PAAL-KNORR SYNTHESIS) 2.2.1.3.2 REACTION OF 1,4-DIENES OR
DIYNES 41 WITH AMINES 2.2.2 RING EXPANSION REACTIONS 43 2.2.3 EXTRUSION
REACTIONS 43 2.3 STRUCTURE 45 2.4 BASICITY 46 2.5 REACTIONS 46 2.5.1
PROTONATION 46 2.5.2 PROTON EXCHANGE 47 2.5.3 ELECTROPHILIC SUBSTITUTION
REACTIONS 49 2.5.3.1 ORIENTATION 50 2.5.3.2 NITRATION 50 2.5.3.3
HALOGENATION 52 2.5.3.3.1 CHLORINATION 52 2.5.3.3.2 BROMINATION 52
2.5.3.3.3 IODINATION 52 2.5.3.4 SULFONATION 54 FIVE-MEMBERED
HETEROCYCLES WITH ONE HETEROATOM 2.5.3.5 ACYLATION 2.5.3.5.1
HOUBEN-HOESCH REACTION 2.5.3.5.2 GATTERMANN FORMYLATION 2.5.3.5.3
VILSMEIER-HAACK REACTION 2.5.3.5.4 FRIEDEL-CRAFTS ACYLATION 2.5.3.6
ALKYLATION 2.5.3.7 HYDROXYMETHYLATION (MANNICH REACTION) 2.5.3.8
REACTIONS WITH ALDEHYDES AND KETONES 2.5.3.9 DIAZO COUPLING 2.5.4
REACTIONS ON CARBON AND NITROGEN ANIONIC SPECIES 2.5.4.1 ALKYLATION
2.5.4.2 ACYLATION 2.5.5 NUCLEOPHJLIC SUBSTITUTION REACTIONS 2.5.6
OXIDATION 2.5.6.1 AUTOXIDATION 2.5.6.2 PHOTO-OXIDATION 2.5.6.3 OXIDATION
WITH CHROMIUM TRIOXIDE 2.5.6.4 OXIDATION WITH HYDROGEN PEROXIDE 2.5.7
REDUCTION 2.5.7.1 CATALYTIC HYDROGENATION 2.5.7.2 REDUCTION BY
METAL-ACID SYSTEMS (CHEMICAL REDUCTION) 2.5.8 REACTIONS WITH FREE
RADICALS 2.5.9 REACTIONS WITH ELECTRON-DEFICIENT SPECIES 2.5.9.1
REACTIONS WITH CARBENES 2.5.9.2 REACTIONS WITH NITRENES 2.5.10
CYCLOADDITION REACTIONS 2.5.10.1 (AN + 2N) REACTIONS 2.5.10.1.1
REACTIONS WITH DMAD 2.5.10.1.2 REACTIONS WITH BENZYNE 2.5.10.1.3
REACTION WITH HEXAFLUOROBICYCLO- [2.2.0]HEXA-2,5-DIENE 2.5.10.2 (2N +
2N) REACTIONS 3 FURANS 3.1 GENERAL 3.2 SYNTHESIS 3.2.1 COMMERCIAL METHOD
(FROM ALDOPENTOSES OR KETOPENTOSES) 3.2.2 FROML,4-DIKETONES 3.2.3
CYCLIZATION OF ALKYNES 3.2.3.1 PHOTOCHEMICAL CYCLIZATION 3.2.3.2 FROM
ALKYNYL SULFONIUM SALTS 3.2.4 CYCLIZATION OF YLIDES 3.2.4.1 SULFUR
YLIDES 3.2.4.2 PHOSPHORUS YLIDES 3.2.5 FROM A-HALOCARBONYL COMPOUNDS
(FEIST-BENARY SYNTHESIS) 3.2.6 RING EXPANSION OF SMALL RING HETEROCYCLES
55 55 56 57 58 58 60 60 64 65 66 66 68 69 69 69 69 69 71 71 72 73 74 74
77 77 77 78 79 80 80 82 82 83 83 83 84 84 84 85 85 86 87 88 6
HETEROCYCLIC CHEMISTRY 3.2.6.1 THREE-MEMBERED HETEROCYCLES 88 3.2.6.2
FOUR-MEMBERED HETEROCYCLES 89 3.2.7 TRANSFORMATION OF FIVE-MEMBERED
HETEROCYCLES 89 3.2.8 RING CONTRACTION 90 3.3 STRUCTURE 91 3.4 REACTIONS
92 3.4.1 REACTIONS WITH ELECTROPHILES 92 3.4.1.1 REACTIVITY AND
ORIENTATION EFFECTS 92 3.4.1.2 DIRECTING EFFECTS OF SUBSTITUENTS 93
3.4.1.3 PROTONATION 94 3.4.1.4 NITRATION 96 3.4.1.5 SULFONATION 97
3.4.1.6 HALOGENATION 98 3.4.1.7 ALKYLATION 100 3.4.1.8 ACYLATION 102
3.4.1.9 REACTIONS WITH ALDEHYDES AND KETONES 104 3.4.1.10 REACTIONS WITH
DIAZONIUM SALTS 105 3.4.2 REACTIONS WITH NUCLEOPHILES 105 3.4.3
REACTIONS WITH FREE RADICALS 108 3.4.4 REACTIONS WITH ELECTRON-DEFICIENT
SPECIES 111 3.4.5 CYCLOADDITION REACTIONS 112 3.4.6 PHOTOCHEMICAL
REACTIONS 118 4 THIOPHENES 121 4.1 GENERAL 121 4.1.1 ISOLATION 122 4.2
SYNTHESIS 122 4.2.1 INTRAMOLECULAR CYCLIZATION REACTIONS 122 4.2.1.1
FROM4-ARALKYLTHIOCROTONONITRILES 122 4.2.1.2 FROM
3-METHYLENETHIOPROPENALS 123 4.2.2 (4+1) CYCLIZATION REACTIONS 124
4.2.2.1 FROM HYDROCARBONS 124 4.2.2.2 FROM 1,4-DIKETONES (PAAL
SYNTHESIS) 125 4.2.3 (3 + 2) CYCLIZATION REACTIONS 126 4.2.3.1 REACTION
OF A,(3-UNSATURATED CARBONYL 126 COMPOUNDS WITH ETHYL MERCAPTOACETATE
4.2.3.2 REACTION OF ACTIVATED ALKYNES WITH 127 A-MERCAPTO KETONES OR
ESTERS 4.2.3.3 REACTION OF DIMETHYL FUMARATE WITH MERCAPTO ESTERS 128
4.2.3.4 REACTION OF A-MERCAPTO KETONES WITH 129 ACTIVATED METHYLENE
NITRILES (GEWALD SYNTHESIS) 4.2.3.5 REACTION OF A-DIKETONES WITH
ACTIVATED 129 METHYLENE COMPOUNDS (HINSBERG SYNTHESIS) 4.2.3.6 REACTION
OF ALKYNES WITH MESOIONIC HETEROCYCLES 131 4.2.4 (2 + 2+1) CYCLIZATION
REACTIONS 131 4.3 STRUCTURE 132 FIVE-MEMBERED HETEROCYCLES WITH ONE
HETEROATOM 7 4.4 REACTIONS 134 4.4.1 REACTIONS WITH ELECTROPHILES 134
4.4.1.1 ELECTROPHILIC SUBSTITUTIONS AT CARBON 134 4.4.1.1.1 ORIENTATION
134 4.4.1.1.2 DIRECTING EFFECTS OF SUBSTITUENTS 135 4.4.1.1.2.1
SUBSTITUENTS AT CARBON-2 135 4.4.1.1.2.2 SUBSTITUENTS AT CARBON-3 136
4.4.1.1.3 PROTONATION 136 4.4.1.1.4 NITRATION 137 4.4.1.1.5 SULFONATION
140 4.4.1.1.6 HALOGENATION 141 4.4.1.1.6.1 CHLORINATION 141 4.4.1.1.6.2
BROMINATION 142 4.4.1.1.6.3 IODINATION 144 4.4.1.1.7 ALKYLATION 144
4.4.1.1.8 ACYLATION 145 4.4.1.1.9 REACTIONS WITH ALDEHYDES AND KETONES
148 4.4.1.1.10 MERCURATION 149 4.4.1.1.11 REACTIONS WITH DIAZONIUM SALTS
150 4.4.1.2 ELECTROPHILIC ATTACK ON SULFUR 151 4.4.2 REACTIONS WITH
OXIDIZING AGENTS 152 4.4.2.1 FORMATION OF THIOPHENE SULFOXIDES AND
SULFONES 152 4.4.2.2 OXIDATIVE RING CLEAVAGE 153 4.4.2.3 OXIDATION BY
METAL IONS 153 4.4.3 REACTIONS WITH NUCLEOPHILES 154 4.4.3.1
NUCLEOPHILIC ATTACK AT CARBON 154 4.4.3.1.1 NUCLEOPHILIC SUBSTITUTIONS
154 4.4.3.1.2 HALOGEN-METAL EXCHANGE 156 4.4.3.2 NUCLEOPHILIC ATTACK AT
HYDROGEN 158 4.4.3.2.1 LITHIATION 158 4.4.3.3 NUCLEOPHILIC RING OPENING
REACTIONS 159 4.4.4 REACTIONS WITH REDUCING AGENTS 160 4.4.4.1 CATALYTIC
REDUCTION 160 4.4.4.2 BIRCH REDUCTION 161 4.4.4.3 REDUCTIVE
DESULFURIZATION 161 4.4.5 REACTIONS WITH FREE RADICALS 161 4.4.6
REACTIONS WITH ELECTRON-DEFICIENT SPECIES 164 4.4.6.1 REACTIONS WITH
CARBENES 164 4.4.6.2 REACTIONS WITH NITRENES 165 4.4.7 CYCLOADDITION
REACTIONS 165 4.4.7.1 THERMAL [4 + 2] CYCLOADDITION REACTIONS 165
4.4.7.2 THERMAL [2 + 2] CYCLOADDITION REACTIONS 167 4.4.7.3
PHOTOCYCLOADDITION REACTIONS 168 4.4.8 PHOTOSUBSTITUTION 170 4.4.9
PHOTOISOMERIZATION 171 REFERENCES 171 CHAPTER BENZO-FUSED FIVE-MEMBERED
HETEROCYCLES WITH ONE HETEROATOM CONTENTS 1 GENERAL 1.1 REACTIVITY 1.2
ORIENTATION 1.3 DIBENZOHETEROCYCLES 2 BENZOPYRROLES 2.1 INDOLES 2.1.1
GENERAL 2.1.2 SYNTHESIS 2.1.2.1 REACTION OF O-NITROTOLUENE WITH DIETHYL
OXALATE (REISSERT INDOLE SYNTHESIS) 2.1.2.2 FROM
O-NITROPHENYLNITROETHYLENE (O,CO-DINITROSTYRENE) 2.1.2.3 PALLADIUM
CATALYZED CYCLIZATION 2.1.2.4 MADELUNG INDOLE SYNTHESIS 2.1.2.5
ISONIRRILE CYCLIZATION 2.1.2.6 BISCHLER INDOLE SYNTHESIS 2.1.2.7 FISCHER
INDOLE SYNTHESIS 2.1.2.8 GASSMAN INDOLE SYNTHESIS 2.1.2.9 NENITZESCU
INDOLE SYNTHESIS 2.1.2.10 FROM PYRROLES 2.1.2.11 FROMAZIRINES 2.1.3
STRUCTURE 2.1.4 REACTIONS 187 188 188 189 190 191 191 194 194 195 196
196 197 198 199 203 203 206 207 208 208 182 HETEROCYCLIC CHEMISTRY 2.2
2.1.4.1 2.1.4.2 2.1.4.3 2.1.4.4 2.1.4.5 2.1.4.6 2.1.4.7 2.1.4.8
REACTIONS WITH ELECTROPHILES 2.1.4.1.1 PROTONATION 2.1.4.1.1.1 REACTION
WITH PROTON ACIDS 2.1.4.1.1.2 BASICITY 2.1.4.1.1.3 H ^^ D EXCHANGE
2.1.4.1.1.4 DIMERIZATION AND TRIMERIZATION 2.1.4.1.2 NITRATION 2.1.4.1.3
NITROSATION 2.1.4.1.4 HALOGENATION 2.1.4.1.4.1 CHLORINATION 2.1.4.1.4.2
BROMINATION 2.1.4.1.4.3 IODINATION 2.1.4.1.5 SULFONATION 2.1.4.1.6
ACYLATION 2.1.4.1.6.1 FRIEDEL-CRAFTS ACYLATION 2.1.4.1.6.2
VILSMEIER-HAACK FORMYLATION 2.1.4.1.7 ALKYLATION 2.1.4.1.8 REACTIONS
WITH ALDEHYDES AND KETONES 2.1.4.1.8.1 EHRLICHTEST 2.1.4.1.8.2 WITH
AROMATIC ALDEHYDES AND KETONES 2.1.4.1.8.3 WITH ALIPHATIC ALDEHYDES AND
KETONES 2.1.4.1.8.4 WITH A,(3-UNSATURATED KETONES 2.1.4.1.9 MANNICH
REACTION REACTIONS ON CARBON AND NITROGEN ANIONIC SPECIES 2.1.4.2.1
ALKYLATION 2.1.4.2.2 ACYLATION REACTIONS WITH NUCLEOPHILES OXIDATION
REDUCTION REACTIONS WITH ELECTRON-DEFICIENT SPECIES REACTIONS WITH FREE
RADICALS CYCLOADDITION REACTIONS ISOINDOLES (BENZO[C]PYRROLES) 2.2.1
GENERA] I 2.2.2 SYNTHESIS 2.2.2.1 CYCLIZATION REACTIONS 2.2.2.1.1 FROM
OC-BROMO-O-TOLUIC ACID 2.2.2.1.2 FROMN-CYANOMETHYL-N-METHYL-O-
CHLOROBENZYLAMINE 209 210 210 211 211 212 212 215 216 216 218 218 220
221 221 222 224 224 224 225 225 227 227 228 229 231 232 233 234 237 238
239 240 240 242 242 242 243 BENZO-FUSED FIVE-MEMBERED HETEROCYCLES WITH
ONE HETEROATOM 183 2.3 2.4 2.2.2.2 2.2.2.3 2.2.2.1.3 FROM 1,4-DIKETONES
EXTRUSION REACTION RING TRANSFORMATION REACTIONS 2.2.2.3.1
FROMPHTHALIMIDINES 2.2.2.3.2 FROMLSOINDOLINES 2.2.2.3.3 FROMPYRROLES
2.2.3 REACTIONS 2.2.3.1 2.2.3.2 2.2.3.3 2.2.3.4 REACTIONS WITH
ELECTROPHILES 2.2.3.1.1 PROTONATION 2.2.3.1.2 NITROSATION 2.2.3.1.3
ACYLATION 2.2.3.1.4 ALKYLATION 2.2.3.1.5 FORMYLATION 2.2.3.1.6 REACTIONS
WITH ALDEHYDES AND KETONES (EHRLICHTEST) OXIDATION REDUCTION
CYCLOADDITION REACTIONS INDOLIZINES (PYRROCOLINES) 2.3.1 GENERAL 2.3.2
SYNTHESIS 2.3.2.1 2.3.2.2 2.3.2.3 2.3.2.4 REACTION OF PYRIDINES WITH
A-HALOCARBONYL COMPOUNDS (TSCHITSCHIBABIN REACTION) REACTION OF PYRIDINE
WITH ALKYNIC COMPOUNDS REACTION OF 2-PYRIDY LLITHIUM WITH
2-CHLOROMETHYLOXIRANE 1,3-DIPOLARCYCLOADDITIONREACTIONS 2.3.3 STRUCTURE
2.3.4 REACTIONS 2.3.4.1 2.3.4.2 2.3.4.3 2.3.4.4 REACTIONS WITH
ELECTROPHILES 2.3.4.1.1 PROTONATION 23 A.I.2 NITRATION 2.3.4.1.3
NITROSATION 2.3.4.1.4 ALKYLATION 2.3.4.1.5 ACYLATION 2.3.4.1.6 REACTIONS
WITH ALDEHYDES AND KETONES OXIDATION REDUCTION CYCLOADDITION REACTIONS
CARBAZOLES (DIBENZOPYRROLES) 2.4.1 GENERAL 2.4.2 SYNTHESIS 243 243 244
244 245 247 247 247 248 249 249 249 250 250 251 252 253 254 254 255 255
257 258 258 259 260 260 261 262 262 263 264 264 264 265 266 267 267 268
184 HETEROCYCLIC CHEMISTRY 2.4.2.1 FROM CYCLOHEXANONE PHENYLHYDRAZONES
(BORSCHE SYNTHESIS OR MODIFIED FISCHER INDOLE SYNTHESIS) 268 2.4.3 2.4.4
2.4.2.2 2.4.2.3 2.4.2.4 2.4.2.5 2.4.2.6 2.4.2.7 2.4.2.8 REACTION OF
ANILINES WITH A-HALOCYCLOHEXANONES FROM DIARYLAMINES 2.4.2.3.1 OXIDATIVE
CYCLIZATION 2.4.2.3.2 PHOTOCHEMICAL CYCLIZATION REDUCTIVE CYCLIZATION OF
O-NITROBIPHENYLS FROM O- AZIDOBIPHENYLS FROM 1-ARYLBENZOTRIAZOLES
(GRAEBE-ULLMANN SYNTHESIS) NENITZESCU REACTION ANNELATION OF INDOLES
STRUCTURE REACTIONS 2.4.4.1 2.4.4.2 2.4.4.3 2.4.4.4 3 BENZOFURANS 3.1
GENERAL REACTIONS WITH ELECTROPHILES 2.4.4.1.1 PROTONATION 2 A A.I.2
NITRATION 2.4.4.1.3 NITROSATION 2.4.4.1.4 CHLORINATION 2.4.4.1.5
BROMINATION 2.4.4.1.6 SULFONATION 2.4.4.1.7 ACYLATION OXIDATION
REDUCTION REACTIONS WITH NUCLEOPHILES 3.2 BENZO[6]FURANS 3.2.1 3.2.2
3.2.3 SYNTHESIS 3.2.1.1 3.2.1.2 3.2.1.3 3.2.1.4 3.2.1.5 3.2.1.6
INTRAMOLECULAR CYCLIZATION OF O-SUBSTITUTED PHENOLS CYCLODEHYDRATION OF
A-ARYLOXYKETONES REACTION OF O-ACYLPHENOLS WITH A-HALO KETONES AND
ESTERS REACTION OF O- ACYLPHENOLS WITH DIMETHYLSULFOXONIUM METHYLIDE
FROM/7-BENZOQUINONES RING CONTRACTION (FROM COUMARINS) STRUCTURE
REACTIONS 3.2.3.1 REACTIONS WITH ELECTROPHILES 3.2.3.1.1 REACTIVITY AND
ORIENTATION 3.2.3.1.2 DIRECTING EFFECTS OF SUBSTITUENTS 268 269 269 270
271 271 272 272 272 273 274 274 274 275 275 276 276 276 277 278 278 279
279 279 282 282 282 283 284 285 286 287 287 288 288 288 289 BENZO-FUSED
FIVE-MEMBERED HETEROCYCLES WITH ONE HETEROATOM 185 3.2.3.1.3 PROTONATION
289 3.2.3.1.4 NITRATION 289 3.2.3.1.5 SULFONATION 291 3.2.3.1.6
HALOGENATION 291 3.2.3.1.6.1 BROMINATION 292 3.2.3.1.6.2 CHLORINATION
293 3.2.3.1.7 ACYLATION 293 3.2.3.1.8 ALKYLATION 294 3.2.3.1.9 REACTION
WITH DIAZONIUM SALTS 295 3.2.3.2 REACTIONS WITH NUCLEOPHILES 295 3.2.3.3
OXIDATION 297 3.2.3.4 REDUCTION 298 3.2.3.5 REACTIONS WITH
ELECTRON-DEFICIENT SPECIES 299 3.2.3.6 CYCLOADDITION REACTIONS 300
3.2.3.7 PHOTOCHEMICAL REACTIONS 300 3.2.3.7.1 PHOTODIMERIZATION 300
3.2.3.7.2 PHOTOSENSITIZED CYCLOADDITION 301 3.2.3.7.3 PHOTOOXYGENATION
301 3.3 BENZO[C]FURANS 302 3.3.1 GENERAL 302 3.3.2 SYNTHESIS 302 3.3.2.1
RETRO-DIELS-ALDER REACTION 302 3.3.2.2 REDUCTIVE CYCLIZATION OF
O-DIBENZOYLBENZENES 303 3.3.2.3 REACTION OF DIBENZOYLACETYLENE WITH
DIENES 303 3.3.2.4 FROM BENZOPHENONES 304 3.3.3 REACTIONS 305 3.3.3.1
CYCLOADDITION REACTIONS 305 3.3.3.2 PHOTOCHEMICAL REACTIONS 307
3.3.3.2.1 PHOTODIMERIZATION 307 3.3.3.2.2 PHOTOCYCLOADDITION 307
3.3.3.2.2.1 WITH CYCLOHEPTATRIENE 307 3.3.3.2.2.2 WITHCYCLOHEXADIENE 308
308 309 309 3.4 DIBENZOFURANS 309 309 310 310 310 311 312 312 3.3.3.3
3.3.3.4 3.3.3.2.3 PHOTOOXYGENATION OXIDATION REDUCTION DIBENZOFURANS
3.4.1 GENERA] 3.4.2 SYNTHESIS 3.4.2.1 3.4.2.2 3.4.2.3 3.4.2.4 FROM 2,2 -
DIHYDROXYBIPHENYLS FROMDIPHENYL ETHERS FROM O- AMINODIPHENYL ETHERS
(PSCHORR TYPE CYCLIZATION) WITTIG REACTION 3.4.3 REACTIONS 186
HETEROCYCLIC CHEMISTRY 3.4.3.1 REACTIONS WITH ELECTROPHILES 312
3.4.3.1.1 BROMINATION 313 3.4.3.1.2 NITRATION 314 3.4.3.1.3 FORMYLATION
316 3.4.3.1.4 SULFONATION 316 3.4.3.2 METALLATION (LITHIATION) 316
3.4.3.3 REACTIONS WITH NUCLEOPHILES 318 3.4.3.4 REDUCTION 319 4
BENZOTHIOPHENES 320 4.1 GENERAL 320 4.2 BENZO[Z ]THIOPHENES 321 4.2.1
GENERAL 321 4.2.2 SYNTHESIS 322 4.2.2.1 OXIDATIVE CYCLIZATION OF
MERCAPTOCINNAMIC ACIDS 322 4.2.2.2 REACTION OFCINNAMIC ACID WITH THIONYL
CHLORIDE 323 4.2.2.3 DEHYDRATIVE CYCLIZATION 323 4.2.2.3.1 FROM
ARYLTHIOACETALDEHYDE ACETALS 323 4.2.2.3.2 FROM ARYLTHIO METHYL KETONES
324 4.2.2.4 REACTION OF MERCAPTOALDEHYDE OR ACID WITH 324 OC-HALO ACIDS
OR KETONES 4.2.2.5 FROMBENZENETHIOLS(THIOPHENOLS) 325 4.2.2.6
FROMTHIOPHENE-2,3-DICARBOXYLIE ANHYDRIDE 326 4.2.3 REACTIONS 327 4.2.3.1
REACTIONS WITH ELECTROPHILES 327 4.2.3.1.1 ELECTROPHILIC ATTACK AT
CARBON 327 4.2.3.1.1.1 ORIENTATION 327 4.2.3.1.1.2 DIRECTING EFFECTS OF
328 SUBSTITUENTS 4.2.3.1.1.3 NITRATION 328 4.2.3.1.1.4 HALOGENATION 328
4.2.3.1.1.5 SULFONATION 329 4.2.3.1.1.6 ALKYLATION 330 4.2.3.1.1.7
ACYLATION 331 4.2.3.1.1.8 DIAZO COUPLING 331 4.2.3.1.2 ELECTROPHILIC
ATTACK AT SULFUR 332 4.2.3.2 REACTIONS WITH OXIDIZING AGENTS 333
4.2.3.2.1 FORMATIONOFL -OXIDES AND 1,1 -DIOXIDES 333 4.2.3.2.2 OXIDATIVE
RING OPENING 334 4.2.3.3 REACTIONS WITH NUCLEOPHILES 334 4.2.3.3.1
METALLATION 334 4.2.3.3.2 RING OPENING BY NUCLEOPHILES 335 4.2.3.3.3
ADDITION OF NUCLEOPHILES 335 4.2.3.4 REACTIONS WITH REDUCING AGENTS 335
BENZO-FUSED FIVE-MEMBERED HETEROCYCLES WITH ONE HETEROATOM 187 4.2.3.5
REACTIONS WITH CARBENES 336 4.2.3.6 CYCLOADDITION REACTIONS 337
4.2.3.6.1 THERMAL (2 + 2) CYCLOADDITION REACTIONS 337 4.2.3.6.2
PHOTOCHEMICAL (2 + 2) CYCLOADDITION 337 REACTIONS 4.2.3.7
PHOTOSUBSTITUTION 338 4.3 BENZO[C]THIOPHENES 339 4.3.1 GENERAL 339 4.3.2
SYNTHESIS 339 4.3.2.1 FROML,4-DIKETONES 339 4.3.2.2 FROM O-BIS
(CHLOROMETHYL) BENZENE 340 4.3.2.3 RING CONTRACTION OF 1,2-DITHIINS 341
4.3.2.4 ANNELATION OF THIOPHENES 341 4.3.3 REACTIONS 341 4.3.3.1
CYCLOADDITION REACTIONS 341 4.3.3.2 OXIDATIVE RING OPENING REACTIONS 342
4.4 DIBENZOTHIOPHENES 343 4.4.1 GENERAL 343 4.4.2 SYNTHESIS 344 4.4.2.1
OXIDATIVE CYCLIZATION OF DIPHENYL SULFIDES 344 4.4.2.2 REDUCTIVE
CYCLIZATION OF DIPHENYL SULFOXIDE 344 4.4.2.3 FROMBIPHENYLS 344 4.4.2.4
FROM DIPHENYL SULFONES 345 4.4.2.5 FROM2-ALLYLBENZO[6]THIOPHENES 345
4.4.3 REACTIONS 346 4.4.3.1 REACTIONS WITH ELECTROPHILES 346 4.4.3.2
REACTIONS WITH NUCLEOPHILES 346 4.4.3.3 OXIDATION 347 REFERENCES 347
CHAPTER * FIVE-MEMBERED HETEROCYCLES WITH TWO HETEROATOMS CONTENTS 1
GENERAL 363 1.1 STRUCTURES 364 1.2 BASICITY 365 1.3 STRUCTURE VERSUS
CHEMICAL REACTIVITY (CONSEQUENCES OF 367 ADDITIONAL NITROGEN ATOM) 1.3.1
REACTIONS WITH ELECTROPHILES 367 1.3.1.1 ELECTROPHILIC ATTACK AT CARBON
367 1.3.1.1.1 ORIENTATION 367 1.3.1.1.1.1 1,3-AZOLES 368 1.3.1.1.1.2
1,2-AZOLES 369 1.3.1.2 ELECTROPHILIC ATTACK AT NITROGEN-3 370 1.3.2
REACTIONS WITH NUCLEOPHILES 371 1.3.2.1 NUCLEOPHILIC ATTACK AT CARBON
371 1.3.2.2 NUCLEOPHILIC ATTACK AT HYDROGEN (DEPROTONATION) 372 2
1,3-AZOLES 374 2.1 IMIDAZOLES 375 2.1.1 GENERAL 375 2.1.2 SYNTHESIS 377
2.1.2.1 REACTION OF A-HYDROXY- OR A-HALO KETONES 377 WITH AMIDINES
2.1.2.2 REACTION OF A-AMINO KETONES WITH CYANATES, 378 THIOCYANATES OR
ISOTHIOCYANATES (MARCKWALD SYNTHESIS) 358 HETEROCYCLIC CHEMISTRY 2.1.2.3
REACTION OF OT-DIKETONES, OC-HYDROXY-, OC-HALO- 378 OR A-AMINO KETONES
WITH FORMAMIDE (FORMAMIDE SYNTHESIS) 2.1.2.4 REACTION OF OXAMIDE WITH
PHOSPHORUS OXYCHLORIDE 379 (WALLACH SYNTHESIS) 2.1.2.5 REACTION OF
ARYLALDOXIMES WITH PROPIOLATE ESTER 380 2.1.2.6 REACTION OF
1,2-DIAMINOALKANES WITH 380 CARBOXYLIC ACIDS AND ALDEHYDES OR KETONES
2.1.2.7 RING TRASFORMATION (FROM OXAZOLES) 381 2.1.2.8 RING CONTRACTION
(FROM PYRAZINES) 381 2.1.3 STRUCTURE 382 2.1.3.1 HYDROGEN BONDING 383
2.1.3.2 TAUTOMERISM 383 2.1.4 REACTIONS 384 2.1.4.1 REACTIVITY 384
2.1.4.2 REACTIONS WITH ELECTROPHILES 385 2.1.4.2.1 ELECTROPHILIC ATTACK
AT NIRTOGEN 385 2.1.4.2.1.1 PROTONATION (BASICITY) 385 2.1.4.2.1.2
N-ALKYLATION 386 2.1.4.2.1.3 N-ACYLATION 387 2.1.4.2.2 ELECTROPHILIC
ATTACK AT CARBON 388 2.1.4.2.2.1 ORIENTATION 388 2.1.4.2.2.2 NITRATION
389 2.1.4.2.2.3 SULFONATION 390 2 A ALL A HALOGENATION 390 2.1.4.2.2.5
ACYLATION 391 2.1.4.2.2.6 DIAZO COUPLING 392 2.1.4.2.2.7 REACTIONS WITH
ALDEHYDES 393 AND KETONES 2.1.4.2.2.8 OXIDATION 394 2.1.4.3 REACTIONS
WITH NUCLEOPHILES 394 2.1.4.3.1 NUCLEOPHILIC ATTACK AT CARBON 394
2.1.4.3.2 NUCLEOPHILIC ATTACK AT 396 HYDROGEN (DEPROTONATION)
2.1.4.3.2.1 DEPROTONATION OF NH (ACIDITY) 396 2.1.4.3.2.2 DEPROTONATION
OF CARBON-2 396 2.1.4.3.2.2.1 H^^D 397 EXCHANGE 2.1.4.3.2.2.2
METALLATION 397 2.1.4.3.2.2.3 C-ACYLATION VIA 398 DEPROTONATION 2.1.4.4
REACTIONS WITH ELECTRON-DEFICIENT SPECIES 398 2.1.4.5 REACTIONS WITH
DIENOPHILES 399 2.1.4.6 PHOTOCHEMICAL CYCLOADDITION REACTIONS 399
FIVE-MEMBERED HETEROCYCLES WITH TWO HETEROATOMS 359 2.2 OXAZOLES 401
2.2.1 GENERAL 401 2.2.2 SYNTHESIS 402 2.2.2.1 CYCLODEHYDRATION OF
A-ACYLAMINO KETONES 402 (ROBINSON-GABRIEL SYNTHESIS) 2.2.2.2 REACTION OF
CC-HALO KETONES WITH PRIMARY 402 AMIDES (BLUMLEIN-LEWY SYNTHESIS)
2.2.2.3 REACTION OF A-HYDROXYAMINO KETONES 402 WITH ALDEHYDES 2.2.2.4
REACTION OF TOSYLMETHYL ISOCYANIDE 403 WITH ALDEHYDES 2.2.2.5 REACTION
OF A-METALLATED ISOCYANIDES WITH 403 ACID DERIVATIVES 2.2.2.6 RING
TRANSFORMATIONS 404 2.2.2.6.1 FROM C-ACYLAZIRIDINES 404 2.2.2.6.2 FROM
ISOXAZOLES (ISOMERIZATION) 405 2.2.3 STRUCTURE 405 2.2.4 REACTIONS 406
2.2.4.1 REACTIVITY 406 2.2.4.2 REACTIONS WITH ELECTROPHILES 407
2.2.4.2.1 ELECTROPHILIC ATTACK AT NITROGEN 407 2.2.4.2.1.1 PROTONATION
(BASICITY) 407 2.2.4.2.1.2 N-ALKYLATION 407 2.2.4.2.2 ELECTROPHILIC
ATTACK AT CARBON 408 2.2.4.2.2.1 BROMINATION 408 2.2.4.2.2.2 MERCURATION
409 2.2.4.2.2.3 VILSMEIER-HAACKFORMYLATION 409 2.2.4.3 REACTIONS WITH
NUCLEOPHILES 410 2.2.4.3.1 NUCLEOPHILIC ATTACK AT CARBON 410 2.2.4.3.2
NUCLEOPHILIC ATTACK AT HYDROGEN 411 2.2.4.3.2.1 METALLATION 411
2.2.4.3.2.2 H^^D EXCHANGE 412 2.2.4.4 THERMAL REACTIONS (CORNFORTH
REARRANGEMENT) 413 2.2.4.5 PHOTOCHEMICAL REACTIONS 413 2.2.4.6
CYCLOADDITION REACTIONS 414 2.2.4.7 PHOTOOXYGENATION 415 2.3 THIAZOLES
416 2.3.1 GENERAL 416 2.3.2 SYNTHESIS 417 2.3.2.1 SYNTHESIS OF THIAZOLES
417 2.3.2.1.1 REACTION OF A-HALO KETONES WITH 417 THIOAMIDES (HANTZSCH S
SYNTHESIS) 2.3.2.1.2 REACTION OF A-ACYLAMINO KETONES WITH 418 PHOSPHORUS
PENTASULFIDE (GABRIEL SYNTHESIS) 360 HETEROCYCLIC CHEMISTRY 2.3.3
2.3.2.1.3 FROM A-AMINONITRILES 418 (COOK-HEILBORN S SYNTHESIS) 2.3.2.1.4
FROM A-THIOCYANO KETONES 419 (TCHERNIAC S SYNTHESIS) 2.3.2.1.5 REACTION
OF A-MERCAPTO KETONES 419 OR A-MERCAPTO ACIDS WITH NITRILES 2.3.2.2
SYNTHESIS OF BENZOTHIAZOLES 421 2.3.2.2.1 SYNTHESIS FROM
O-AMINOTHIOPHENOLS 421 (2-AMINOBENZENETHIOLS) 2.3.2.2.1.1 REACTION WITH
ALDEHYDES 421 2.3.2.2.1.2 REACTION WITH 1,2-DIKETONES 421 2.3.2.2.1.3
REACTION WITH ACIDS AND 422 ACID DERIVATIVES 2.3.2.2.2 FROM
ARYLTHIOUREAS (HUGERSHOFF S METHOD) 422 STRUCTURE 422 2.3.4 REACTIONS
2.3.4.1 2.3.4.2 2.3.4.3 2.3.4.4 2.3.4.5 2.3.4.6 3 1,2-AZOLES 3.1
PYRAZOLES 3.1.1 GENERA REACTIONS WITH ELECTROPHILES 2.3.4.1.1
ELECTROPHILIC ATTACK AT NITROGEN 2.3.4.1.1.1 BASICITY 2.3.4.1.1.2 N-ALKY
LATION (REACTION WITH ALKYL HALIDES) 2.3.4.1.2 ELECTROPHILIC ATTACK AT
CARBON 2.3.4.1.2.1 NITRATION 2.3.4.1.2.2 SULFONATION 2.3.4.1.2.3
HALOGENATION 2.3.4.1.2.4 ALKYLATION 2.3.4.1.2.5 MERCURATION 2.3.4.1.2.6
DIAZO COUPLING CONDENSATION REACTIONS OXIDATION DESULFURIZATION
REACTIONS WITH NUCLEOPHILES 2.3.4.5.1 NUCLEOPHILIC ATTACK AT CARBON
2.3.4.5.1.1 AMINATION 2.3.4.5.1.2 RING CLEAVAGE 2.3.4.5.1.3 DISPLACEMENT
OF HALIDE 2.3.4.5.1.4 METAL-HALOGEN EXCHANGE 2.3.4.5.2 NUCLEOPHILIC
ATTACK AT HYDROGEN 2.3.4.5.2.1 METALLATION 2.3.4.5.2.2 H ^I D EXCHANGE
PHOTOCHEMICAL REARRANGEMENTS I 3.1.2 SYNTHESIS 423 423 423 424 424 425
425 425 426 427 427 427 428 429 430 430 430 430 431 431 432 432 432 433
434 435 435 435 436 FIVE-MEMBERED HETEROCYCLES WITH TWO HETEROATOMS 361
3.1.2.1 (3 + 2) CYCLIZATION REACTIONS 436 3.1.2.1.1 REACTION OF
(3-DIKETONES WITH HYDRAZINES 436 3.1.2.1.2 REACTION OF A,P-UNSATURATED
CARBONYL 437 COMPOUNDS WITH HYDRAZINES 3.1.2.2 1,3-DIPOLARCYCLOADDITIONS
439 3.1.3 STRUCTURE 440 3.1.3.1 HYDROGEN BONDING 441 3.1.3.2 TAUTOMERISM
441 3.1.4 REACTIONS 442 3.1.4.1 REACTIVITY 442 3.1.4.2 ELECTROPHILIC
ATTACK AT NITROGEN 443 3.1.4.2.1 BASICITY 443 443 443 443 445 445 445
447 448 449 449 450 450 451 451 451 452 452 452 453 453 454 455 455 458
3.2.2.1 REACTION OF P-DIKETONES WITH HYDROXYLAMINE 458 3.2.2.2 REACTION
OF NITRILE N-OXIDES 459 WITH ALKENES AND ALKYNES 3.2.3 REACTIONS 460
3.2.3.1 REACTIVITY 460 3.2.3.2 REACTIONS WITH ELECTROPHILES 461
3.2.3.2.1 ELECTROPHLIC ATTACK AT NITROGEN 461 3.2.3.2.1.1 BASICITY 461
3.1.4.3 3.1.4.4 3.1.4.5 3.1.4.6 3.1.4.7 3.1.4.8 3.1.4.9 3.2 ISOXAZOLES
3.2.1 GENERAL 3.1.4.2.2 3.1.4.2.3 3.1.4.2.4 3.1.4.2.5 ACIDITY
N-ALKYLATION N-ACYLATION MICHAEL ADDITION ELECTROPHILIC ATTACK AT CARBON
3.1.4.3.1 3.1.4.3.2 3.1.4.3.3 3.1.4.3.4 3.1.4.3.5 3.1.4.3.6 OXIDATION
REDUCTION REACTIONS 3.1.4.6.1 3.1.4.6.2 REACTIONS REACTIVITY AND
ORIENTATION NITRATION SULFONATION HALOGENATION MERCURATION DIAZO
COUPLING WITH NUCLEOPHILES NUCLEOPHILIC ATTACK AT CARBON NUCLEOPHILIC
ATTACK AT HYDROGEN 3.1.4.6.2.1 METALLATION 3.1.4.6.2.2 RING CLEAVAGE VIA
DEPROTONATION WITH ELECTRON-DEFICIENT SPECIES CYCLOADDITION REACTIONS
PHOTOCHEMICAL TRANSFORMATION , 3.2.2 SVNTHESIS 362 HETEROCYCLIC
CHEMISTRY 3.2.3.2.2 3.2.3.2.1.2 N-ALKYLATION ELECTROPHILIC ATTACK AT
CARBON 3.2.3.2.2.1 3.2.3.2.2.2 3.2.3.2.2.3 3.2.3.2.2.4 3.2.3.2.2.5
3.2.3.2.2.6 H ^ D EXCHANGE NITRATION SULFONATION HALOGENATION
CHLOROMETHYLATION AND HYDROXYMETHYLATION MERCURATION 3.2.3.3 OXIDATION
3.2.3.4 REACTIONS WITH NUCLEOPHILES 3.2.3.4.1 NUCLEOPHILIC DISPLACEMENT
3.2.3.4.2 RING CLEAVAGE VIA C-DEPROTONATION 3.2.3.4.3 REDUCTIVE RING
CLEAVAGE 3.2.3.5 CONDENSATION REACTIONS 3.2.3.6 REARRANGEMENT 3.2.3.7
PHOTOCHEMICAL AND THERMAL REACTIONS 3.3 ISOTHIAZOLES 3.3.1 GENERAL 3.3.2
SYNTHESIS 3.3.2.1 OXIDATIVE CYCLIZATION OF Y-IMINOTHIOLS 3.3.2.2 RING
TRANSFORMATION 3.3.2.3 FROM ALKENES 3.3.2.4 FROM A,(3-UNSATURATED
CARBONYL COMPOUNDS 3.3.3 STRUCTURE 3.3.4 REACTIONS 3.3.4.1 REACTIONS
WITH ELECTROPHILES 3.3.4.1.1 NITRATION 3.3.4.1.2 SULFONATION 3.3.4.1.3
N-ALKYLATION 3.3.4.2 SIDE CHAIN REACTIVITY 3.3.4.2.1 REACTION WITH
AROMATIC ALDEHYDES 3.3.4.2.2 DECARBOXYLATION 3.3.4.3 REACTIONS WITH
NUCLEOPHILES 3.3.4.3.1 NUCLEOPHILIC SUBSTITUTIONS 3.3.4.3.2 RING
TRANSFORMATION 3.3.4.3.3 LITHIATION 3.3.4.3.4 RING CLEAVAGE 3.3.4.4
PHOTOCHEMICAL TRANSFORMATION 3.3.4.5 OXIDATION REFERENCES 461 461 462
463 464 465 466 466 467 468 468 468 471 471 472 472 473 473 474 474 475
476 476 477 478 478 478 479 479 480 480 480 480 480 481 482 482 482 483
483 CHAPTER FIVE-MEMBERED HETEROCYCLES WITH MORE THAN TWO HETEROATOMS
CONTENTS 1 GENERAL 1.1 EFFECTS OF ADDITIONAL NITROGEN ATOMS 2
TRIAZOLESANDTETRAZOLES 2.1 1,2,3-TRIAZOLES 2.1.1 GENERAL 2.1.2 SYNTHESIS
2.1.2.1 OXIDATIVE CYCLIZATION OF BIS-HYDRAZONES OF OT-DIKETONES 2.1.2.2
CYCLOADDITION OF AZIDES WITH ALKYNES 2.1.3 REACTIONS 2.1.3.1 AMPHOTERIC
NATURE 2.1.3.2 ELECTROPHILIC SUBSTITUTIONS 2.1.3.2.1 ALKYLATION
2.1.3.2.2 ACYLATION 2.1.3.2.3 BROMINATION 2.1.3.3 THERMAL AND
PHOTOCHEMICAL REACTIONS 2.1.3.4 DIMROTH REARRANGEMENT 2.1.3.5 RING
CLEAVAGE REACTIONS 2.2 1,2,4-TRIAZOLES 2.2.1 GENERAL 2.2.2 SYNTHESIS
2.2.2.1 FROM HYDRAZINE DERIVATIVES 2.2.2.2 FROMNITRILIMINES 2.2.3
STRUCTURE 491 492 492 492 492 493 493 494 495 495 496 497 498 498 499
501 502 503 503 504 504 505 506 488 HETEROCYCLIC CHEMISTRY 2.2.4
REACTIONS 2.2A.I ACIDITY-BASICITY 2.2.4.2 REACTIVITY 2.2.4.2.1
REACTIONS WITH ELECTROPHILES 2.2.4.2.1.1 ELECTROPHILIC ATTACK AT
NITROGEN 2.2.4.2.1.2 QUATERNIZATION 2.2.4.2.1.3 ELECTROPHILIC ATTACK AT
CARBON 2.2.4.2.2 REACTIONS WITH NUCLEOPHILES 2.2.4.2.3 REACTIONS WITH
ELECTRON-DEFICIENT SPECIES 2.2.4.2.3.1 REACTIONS WITH NITRENES
2.2.4.2.3.2 REACTIONS WITH CARBENES OXIDATION THERMAL AND PHOTOCHEMICAL
REACTIONS 2.2.4.2.4 2.2.4.2.5 2.3 TETRAZOLES 2.3.1 GENERAL 2.3.2
SYNTHESIS 2.3.2.1 FROM IMIDOYL CHLORIDES 2.3.2.2 FROM AMIDRAZONES
2.3.2.3 FROMNITRILES 2.3.2.4 FROM NITRILIUM SALTS 2.3.2.5 FROM
ISONITRILES 2.3.3 STRUCTURE 2.3.3.1 HYDROGEN BONDING 2.3.4 REACTIONS
2.3.4.1 REACTIONS WITH ELECTROPHILES 2.3.4.2 REACTIONS WITH NUCLEOPHILES
2.3.4.2.1 NUCLEOPHILIC ATTACK AT HYDROGEN 2.3.4.2.1.1 ACIDITY
2.3.4.2.1.2 H T^X D EXCHANGE 2.3.4.2.1.3 METALLATION 2.3.4.2.2
NUCLEOPHILIC ATTACK AT C-5 (NUCLEOPHILIC SUBSTITUTIONS) 2.3.4.3 THERMAL
AND PHOTOCHEMICAL REACTIONS 522 2.3.4.3.1 REACTIONS INVOLVING 522
NITRILIRNINE INTERMEDIATES 2.3.4.3.2 REACTIONS INVOLVING CARBENE
INTERMEDIATES 524 2.3.4.3.3 REACTIONS INVOLVING NITRENE INTERMEDIATES
524 REARRANGEMENTS 525 525 526 527 506 506 507 508 508 509 509 510 511
511 511 512 512 513 513 513 513 515 516 516 517 517 518 519 519 520 520
520 521 521 522 2.3.4.4 3 OXADIAZOLES 3.1 1,2,3-OXADIAZOLES 3.2
1,2,4-OXADIAZOLES 3.2.1 GENERAL 3.2.2 SYNTHESIS 3.2.2.1 CYCLIZATION
REACTIONS (FROM AMIDOXIMES) 527 528 528 FIVE-MEMBERED HETEROCYCLES WITH
MORE THAN TWO HETEROATOMS 489 3.2.2.2 1,3-DIPOLARCYCLOADDITIONS 528
3.2.3 STRUCTURE 529 3.2.4 REACTIONS 529 3.2.4.1 ELECTROPHILIC
SUBSTITUTION REACTIONS 529 3.2.4.2 NUCLEOPHILIC SUBSTITUTION REACTIONS
530 3.2.4.3 REACTIONS OF SUBSTITUENTS 530 3.2.4.4 REDUCTION 531 3.2.4.5
RING CLEAVAGE VIA C-DEPROTONATION 532 3.2.4.6 PHOTOCHEMICAL REACTIONS
532 3.2.4.7 REARRANGEMENTS 533 3.3 1,2,5-OXADIAZOLES 533 3.3.1 GENERAL
533 3.3.2 SYNTHESIS 534 3.3.2.1 FURAZANS 534 3.3.2.1.1 DEHYDRATION OF
A-DIOXIMES 534 3.3.2.1.2 RING TRANSFORMATIONS 534 3.3.2.2 FUROXANS 535
3.3.2.2.1 OXIDATION OF A-DIOXIMES 535 3.3.2.2.2 DEHYDRATION OF A-NITRO
KETONE OXIMES 536 3.3.3 STRUCTURE 536 3.3.4 REACTIONS 537 3.3.4.1
REACTIONS WITH ELECTROPHILES 537 3.3.4.2 REACTIONS WITH NUCLEOPHILES 537
3.3.4.3 RING CLEAVAGE VIA C-DEPROTONATION 538 3.3.4.4 REARRANGEMENTS 539
3.3.4.5 THERMAL AND PHOTOCHEMICAL REACTIONS 539 3.4 1,3,4-OXADIAZOLES
540 3.4.1 GENERAL 540 3.4.2 SYNTHESIS 541 3.4.2.1 FROM DIACYLHYDRAZINES
541 3.4.2.2 RING TRANSFORMATION 541 3.4.3 STRUCTURE 542 3.4.4 REACTIONS
543 3.4.4.1 REACTIONS WITH ELECTROPHILES 543 3.4.4.2 REACTIONS WITH
NUCLEOPHILES 544 3.4.4.2.1 NUCLEOPHILIC SUBSTITUTION REACTIONS 544
3.4.4.2.2 NUCLEOPHILIC ATTACK WITH RING CLEAVAGE 545 3.4.4.3 THERMAL AND
PHOTOCHEMICAL REACTIONS 546 4 THIADIAZOLES 547 4.1 1,2,3-THIADIAZOLES
547 4.1.1 GENERAL 547 4.1.2 SYNTHESIS 547 4.1.2.1 PACHMANN AND NOLD
SYNTHESIS 547 4.1.2.2 HURD-MORI S CLASSICAL SYNTHESIS 548 (FROM
HYDRAZONES) 490 HETEROCYCLIC CHEMISTRY 4.2 4.3 4.4 4.1.3 4.1.4 STRUCTURE
REACTIONS 4.1.4.1 REACTIONS WITH ELECTROPHILES 4.1.4.1.1 ELECTROPHILIC
ATTACK AT NITROGEN 4.1.4.2 REACTIONS WITH NUCLEOPHILES 4.1.4.2.1
NUCLEOPHILIC SUBSTITUTIONS 4.1.4.2.2 RING CLEAVAGE VIA C-DEPROTONATION
4.1.4.2.3 NUCLEOPHILIC ATTACK AT SULFUR 4.1.4.3 OXIDATION 4.1.4.4
THERMAL AND PHOTOCHEMICAL REACTIONS 4.1.4.4.1 THERMAL REACTIONS
4.1.4.4.2 PHOTOCHEMICAL REACTIONS 4.1.4.4.3 REARRANGEMENTS
1,2,4-THIADIAZOLES 4.2.1 4.2.2 4.2.3 4.2.4 GENERAL SYNTHESIS 4.2.2.1
OXIDATIVE CYCLIZATION OF THIOACYLAMIDINES 4.2.2.2 FROM AMIDINES 4.2.2.3
HETEROCYCLIC RING TRANSFORMATIONS (OXAZOLE AND OXADIAZOLE
REARRANGEMENTS) STRUCTURE REACTIONS 4.2.4.1 REACTIVITY 4.2.4.2 REACTIONS
WITH ELECTROPHILES 4.2.4.3 REACTIONS WITH NUCLEOPHILES 4.2.4.3.1
NUCLEOPHILIC SUBSTITUTION REACTIONS 4.2.4.3.2 RING CLEAVAGE 4.2.4.3.2.1
NUCLEOPHILIC ATTACK AT CARBON 4.2.4.3.2.2 NUCLEOPHILIC ATTACK AT SULFUR
4.2.4.3.3 NUCLEOPHILIC ATTACK AT HYDROGEN 4.2.4.4 REDUCTION
1,2,5-THIADIAZOLES 4.3.1 4.3.2 4.3.3 4.3.4 GENERAL SYNTHESIS 4.3.2.1
FROM O-DIAMINES [(4+1) CYCLIZATION] STRUCTURE REACTIONS 4.3.4.1
STABILITY 4.3.4.2 REACTIONS WITH ELECTROPHILES 4.3.4.3 REACTIONS WITH
NUCLEOPHILES 1,3,4-THIADIAZOLES 4.4.1 4.4.2 GENERAL SYNTHESIS 549 549
549 549 550 550 550 551 551 552 552 552 553 553 553 554 554 554 555 557
557 557 557 559 559 560 560 560 560 561 561 561 562 562 563 563 563 564
564 566 566 567 FIVE-MEMBERED HETEROCYCLES WITH MORE THAN TWO
HETEROATOMS 491 4.4.2.1 FROM THIOSEMICARBAZIDES 4.4.2.2
FROMDIMETHYLFORMAMIDE 4.4.2.3 FROM HYDRAZINE 4.4.3 STRUCTURE 4.4.4
REACTIONS 4.4.4.1 REACTIVITY 4.4.4.2 REACTIONS WITH ELECTROPHILES
4.4.4.2.1 ELECTROPHILIC ATTACK AT NITROGEN (QUATERNIZATION) 4.4.4.2.2
ELECTROPHILIC ATTACK AT CARBON 4.4.4.3 REACTIONS WITH NUCLEOPHILES
4.4.4.3.1 H ^I D EXCHANGE 4.4.4.3.2 RING CLEAVAGE VIA C-DEPROTONATION
4.4.4.3.3 AMINATION 4.4.4.3.4 NUCLEOPHILIC SUBSTITUTIONS 4.4.4.4
REACTIONS INVOLVING RING FORMATION NCES 567 568 568 569 569 569 569 569
570 570 570 570 571 571 572 573 CHAPTER MESO-IONIC HETEROCYCLES CONTENTS
1 GENERAL 581 2 CLASSIFICATION 583 3 CHEMISTRY OF MESO-IONIC
HETEROCYCLES 584 3.1 CHEMISTRY OF MESO-IONIC HETEROCYCLES OF TYPE-A 584
3.1.1 L,3-OXAZOLIUM-4-OLATES 585 3.1.1.1 SYNTHESIS 585 3.1.1.1.1 FROM
A-DIAZOIMIDES (DIAZO KETONES) 585 3.1.1.1.2 FROMLMIDES 585 3.1.1.2
REACTIONS 585 3.1.2 L,3-OXAZOLIUM-5-OLATES(MUNCHNONES) 587 3.1.2.1
SYNTHESIS 587 3.1.2.1.1 FROM N-ACYLAMINO ACIDS 587 3.1.2.2 REACTIONS 588
3.1.2.2.1 CYCLOADDITION REACTIONS 588 3.1.2.2.1.1 REACTIONS WITH ALKENES
588 AND RELATED COMPOUNDS 3.1.2.2.1.2 REACTIONS WITH ALKYNES 592
3.1.2.2.1.3 REACTIONS WITH CARBONYL 593 COMPOUNDS 3.1.2.2.1.4 REACTION
WITH CARBON DISULFIDE 594 3.1.2.2.1.5 REACTIONS WITH ISOTHIOCYANATES 594
AND ISOCYANATES 3.1.2.2.2 REACTIONS WITH NUCLEOPHILES 595 580
HETEROCYCLIC CHEMISTRY 3.2 3.1.3 3.1.4 3.1.5 3.1.6 3.1.7 3.1.8 3.1.2.2.3
REACTIONS WITH SMALL RING HETEROCYCLES 3.1.2.2.4 PHOTOCHEMICAL REACTIONS
1,3-OXATHIOLIUM-4-OLATES 3.1.3.1 SYNTHESIS 3.1.3.2 REACTIONS
1,3-OXATHIOLIUM-5-OLATES 3.1.4.1 SYNTHESIS 3.1.4.2 REACTIONS
1,3-DIAZOLIUM-4-OLATES 3.1.5.1 SYNTHESIS 3.1.5.1.1 FROM AMINO AMIDES
3.1.5.1.2 FROMAMIDINES 3.1.5.1.3 FROM 1,3-OXAZOLIUM-5-OLATES 3.1.5.2
REACTIONS 1,3-DIAZOLIUM-4-AMINIDES 3.1.6.1 SYNTHESIS 3.1.6.2 REACTIONS
1,3-DITHIOLIUM-4-OLATES 3.1.7.1 SYNTHESIS 3.1.7.1.1 FROM DITHIOGLYCOLIC
ACIDS 3.1.7.1.2 FROM DITHIOBENZOIC ACIDS 3.1.7.2 REACTIONS 3.1.7.2.1
CYCLOADDITION WITH ALKYNES 3.1.7.2.2 CYCLOADDITION WITH ALKENES
3.1.7.2.3 CYCLOADDITION WITH COMPOUNDS CONTAINING CARBON-HETEROATOM
DOUBLE BONDS 3.1.7.2.4 PHOTOCHEMICAL CYCLOADDITION
1,2,3-OXADIAZOLIUM-5-OLATES (SYDNONES) 3.1.8.1 SYNTHESIS 3.1.8.1.1 FROM
N-NITROSO-A-AMINO ACIDS 3.1.8.2 REACTIONS 3.1.8.2.1 CYCLOADDITIONS WITH
ALKYNES 3.1.8.2.2 CYCLOADDITIONS WITH ALKENES 3.1.8.2.3 PHOTOCHEMICAL
REACTIONS CHEMISTRY OF MESO-IONIC HETEROCYCLES OF TYPE-B 3.2.1
1,2-DIAZOLIUM-4-AMINIDES 3.2.1.1 SYNTHESIS 3.2.1.2 REACTIONS 3.2.1.2.1
THERMAL ISOMERIZATION 596 596 597 597 598 598 599 599 600 600 600 600
601 601 601 602 603 604 604 604 605 605 606 606 607 607 609 609 609 609
610 611 612 614 614 614 615 615 MESO-IONIC HETEROCYCLES 581 3.2.1.2.2
REACTION WITH DMAD 3.2.2 L,2-DITHIOLIUM-4-OLATES 3.2.2.1 3.2.2.2
SYNTHESIS 3.2.2.1.1 FROM PROPANE-1,3-DIONE ESTERS 3.2.2.1.2 FROM
1,3-DIARYLPROPANE- ,2,3-TRIONES 3.2.2.1.3 FROM L,L,3,3-TETRABROMO-L,3-
DIARYLPROPAN-2-ONES REACTIONS 3.2.2.2.1 DESULFURIZATION 3.2.2.2.2
REACTIONS WITH AMMONIA AND ITS DERIVATIVES 3.2.2.2.3 THERMAL REACTIONS
3.2.3 L,2,3,4-TETRAZOLIUM-5-THIOLATES 3.2.3.1 3.2.3.2 SYNTHESIS
3.2.3.1.1 FROM DITHIZONE 3.2.3.1.2 FROM DIPHENYLTHIOCARBAZIDE REACTIONS
3.2.3.2.1 ALKYLATION 3.2.3.2.2 THERMAL REARRANGEMENT 3.2.3.2.3
CYCLOADDITION REACTIONS 3.2.3.2.4 REACTIONS INVOLVING DEHYDRODITHIZONE
AS ACYCLIC VALENCE TAUTOMER 616 616 616 616 617 617 618 618 618 620 620
620 620 621 621 621 621 622 623 REFERENCES 624 PPN: 074886932 TITEL:
HETEROCYCLIC CHEMISTRY / R. R. GUPTA; M. KUMAR; V. GUPTA. - BERLIN :
SPRINGER, 1999 ISBN: 3-540-65252-3 BIBLIOGRAPHISCHER DATENSATZ IM
SWB-VERBUND
|
| any_adam_object | 1 |
| author | Gupta, Radha R. 1941- Kumar, Mahendra 1957- Gupta, Vandana 1966- |
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| author_facet | Gupta, Radha R. 1941- Kumar, Mahendra 1957- Gupta, Vandana 1966- |
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| id | DE-604.BV012755444 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T18:33:05Z |
| institution | BVB |
| isbn | 3540652523 |
| language | English |
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| spelling | Gupta, Radha R. 1941- Verfasser (DE-588)120453320 aut Heterocyclic chemistry 2 Five-membered heterocycles R. R. Gupta ; M. Kumar ; V. Gupta Berlin [u.a.] Springer 1999 X, 638 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Kumar, Mahendra 1957- Verfasser (DE-588)120453355 aut Gupta, Vandana 1966- Verfasser (DE-588)120453401 aut (DE-604)BV012237381 2 SWB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=008672959&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Gupta, Radha R. 1941- Kumar, Mahendra 1957- Gupta, Vandana 1966- Heterocyclic chemistry |
| title | Heterocyclic chemistry |
| title_auth | Heterocyclic chemistry |
| title_exact_search | Heterocyclic chemistry |
| title_full | Heterocyclic chemistry 2 Five-membered heterocycles R. R. Gupta ; M. Kumar ; V. Gupta |
| title_fullStr | Heterocyclic chemistry 2 Five-membered heterocycles R. R. Gupta ; M. Kumar ; V. Gupta |
| title_full_unstemmed | Heterocyclic chemistry 2 Five-membered heterocycles R. R. Gupta ; M. Kumar ; V. Gupta |
| title_short | Heterocyclic chemistry |
| title_sort | heterocyclic chemistry five membered heterocycles |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=008672959&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV012237381 |
| work_keys_str_mv | AT guptaradhar heterocyclicchemistry2 AT kumarmahendra heterocyclicchemistry2 AT guptavandana heterocyclicchemistry2 |