Click reactions in organic synthesis:
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| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH Verlag GmbH & Co. KGaA
[2016]
|
| Subjects: | |
| Online Access: | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-33916-7/ Inhaltsverzeichnis |
| Physical Description: | XVI, 341 Seiten Illustrationen, Diagramme |
| ISBN: | 9783527339167 9783527694174 |
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Record in the Search Index
| _version_ | 1804176525814136832 |
|---|---|
| adam_text | CONTENTS
LIST OF CONTRIBUTORS X I
PREFACE X V
1 CLICK CHEMISTRY: MECHANISTIC AND SYNTHETIC PERSPECTIVES 1
RAMESH RAMAPARIICKER AND POONOM CHAUHON
1.1 C YCLOADDITION C LICK REACTIONS 2
1.1.1 A Z ID E -A LK Y N E HUISGEN 1,3-DIPOLAR C YCLOADDITION 2
1.1.2 COPPER-CATALYZED A Z ID E -A LK Y N E C YCLOADDITION (CUAAC) C
LICK
REACTION 2
MECHANISM O F CUAA C C LICK REACTIONS 5
1.1.2.2 CATALYSTS USED FO R C UAAC C LICK REACTIONS 6
1.1.2.3 LIGANDS USED FOR C UAA C C LICK REACTIONS 7
1.1.3 RUTHENIUM -CATALYZED A Z ID E -A LK Y N E C YCLOADDITION (RUAAC) C
LICK
REACTIONS 7
MECHANISM O F RUAAC C LICK REACTIONS 8
1.1.4 STRAIN-PROM OTED A Z ID E -A LK Y N E C YCLOADDITION (SPAAC)
REACTIONS 8
1.1.5 ORGANOCATALYTIC TRIAZOLE FORMATION 10
1.2 THIOL-BASED C LICK REACTIONS 12
1.2.1 RADICAL C LICK REACTIONS O F ^ I O LS 12
T H IO L-E N E RADICAL C LICK REACTION 12
1.2.1.2 THIN]_*NP RADICAL C LICK REACTION 14
1.2.2 N UCLEOPHILIC A D D ITIO N C LICK REACTIONS O F ^ I O LS 15
1.2.2.1 ^ IO L- E P O X ID E C LICK REACTIONS 17
1.2.2.2 * IO L-IS O C Y A N A TE C LICK REACTIONS 17
1.2.2.3 T H IO L-M IC H A E L A D D ITIO N C LICK REACTIONS 18
1.2.2.4 ^ IO L- H A LO G E N N UCLEOPHILIC SUBSTITUTION REACTION 20
1.3 MISCELLANEOUS C LICK REACTIONS 21
REFERENCES 22
2.2.3
2.2.3.1
2.2.3.2
2.2.3.3
2.2.3.4
2.2.35
2.2.3.6
2.2.3.7
2.2.3.8
2.2.3.9
2.2.3.10
2.2.3.11
2.2.3.12
2.2.3.13
2.2.3.14
2.2.3.15
2.2.3.16
2.2.3.17
2.2.3.18
2.3
2
.
2.1
2.3.1.1
2.3.1.2
2.3.2
2.3.2.1
2.3.3
2.3.4
2.35
2.3.5.1
2.3.6
2.3.7
2.38
2.3.8.1
APPLICATIONS OF CLICK CHEMISTRY IN DRUG DISCOVERY AND
DEVELOPMENT 25
BALASUBRAMANIAN GOPOLAN ARID KALPATTU KUPPUSAMY BALOSUBRAMANIAN
IN TRO D U CTIO N 25
PART A: A PPLICATION O F CLICK C HEM ISTRY TO D RUG DISCOVERY AND
DEVELOPMENT 25
CARBONIC ANHYDRASE INHIBITORS 30
TARGETING ONCHOCERCA VOLVULUS CHITINASE*L (O V C H T L) USING THE
H YDROXYTRIAZOLE M OIETY W ITH IN A SCAFFOLD HOPPING APPROACH 32
L,2 ,3 *TRIAOLE*DERIVED ANTICANCER AGENTS 34
TOPOISOMERASE II INHIBITORS 34
HISTONE DEACETYLASE INHIBITORS 36
PROTEIN TYROSINE KINASE INHIBITORS 38
A NTIM ICROTUBULE AGENTS 39
HSP 90 INHIBITORS 40
A UTOPHAGYD EPENDENT APOPTOSIS IN CANCER * * ** * * 41
ANTICANCER A C TIV ITY 0 F4 SS *TRIAZ01E-P0D0PHYLL0T0XIN 42
1
*
2,3-TRIAZ01E-SUBSTITUTED OLEANOLIC A CID DERIVATIVES AS ANTICANCER
42
A NTI-IN FE CTIVE AGENTS 43
L,2 ,3 *TRIAZOLE NUCLEOSIDE 44
L
*
2,3-TRIAZOLECARBONUCLEOSIDES 45
SS_LACTAMASE INHIBITORS AS A NTIBACTERIAL AGENTS 47
1,2,3-TRIAZOLE-LINKED CARBAZOLES AS A NTITUBERCULAR AGENTS 48
L,4 -D IA RY L*SUBSTITUTED 1,2,3-TRAIZOLES AS ANTIM YCOBACTERIAL (M TB)
K * EIITS 48
L,2 ,3 *TRIAZOLE*ADAMANTYLACETAMIDE HYBRIDS AS A NTITUBERCULAR
AGENTS 50
NON-NUCLEOSIDE H IV INTEGRASE INHIBITORS 50
MISCELLANEOUS TE R A P E U TIC SEGMENTS: 1,2,3-TRIAZOLE-LINKED
DOPAMINE D3 RECEPTOR (D3R) 53
PEPTIDOMIMETICS: 1,2,3-TRIAZOLE AS A DISULFIDE BOND M IM E TIC 53
PART B: SYNTHESIS O F TRIAZOLE-BASED DRUGS C URRENTLY IN USE 54
TAZOBACTAM 54
SYNTHESIS O F TAZOBACTAM FROM INTERM EDIATE 102 55
O THER REPORTS ON TAZOBACTAM SYNTHESIS 55
SOLITHROM YCIN 56
SYNTHESIS O F SOLITHROM YCIN 57
CEFATRIZINE 60
RADEZOLID 61
M OLIDUSTAT 63
SYNTHESIS O F M O D U S TA T 63
TRADIPITANT 63
CARBOXYAMIDOTRIAZOLE 66
RUFINAMIDE 66
R UFINAM IDE*NOVARTIS PROCESS 66
1
2
2
.
2
.
2.2.
2.2
*
:
32.13
3.2.1.4
3.2.1.5
3.2.1.6
3.2.1.7
3.2.2
3.2.2.1
3.2.2.2
322.3
3.2.2.4
3.2.2.5
3.2.2.6
3.2.2.7
3.2.2.8
3.2.2.9
3.2.2.10
3.2.2.11
3.3
3.4
3.4.1
^411
3.4.1.2
3.4.1.3
3.4.1.4
3.5
GREEN CHEMICAL SYNTHESIS AND CLICK REACTIONS 77
MARIA JOSE AREVALO, OSCAR LOPEZ, ONDMARIA VICTORIA GIL
IN TRO D U CTIO N 77
HUISGEN 1,3-DIPOLAR C YCLOADDITION 77
GREEN PERSPECTIVES ON REACTION C ONDITIONS 78
COPPER(I) CATALYSTS 78
COPPER(I) COMPLEXES W ITH N ITROGEN- AND PHOSPHOROUS* DONATING
LIGANDS 79
METALATED REAGENTS AS CATALYSTS 82
IM M OBILIZED COPPER SPECIES 82
COPPER NANOCATALYSIS 83
O THER METALS AS CATALYSTS 84
N ONCONVENTIONAL ENERGY SOURCES 85
APPLICATIONS TO SYNTHESIS 85
REGIOSELECTIVITY O F THE A LK Y N E -A Z ID E CYCLOADDITION 85
D IFFERENT SUBSTITUTION PATTERNS ON TRIAZOLE 86
STRAIN-PROM OTED CYCLOADDITIONS 87
SULFONYL AZIDES IN HUISGEN C YCLOADDITION 87
SYNTHESIS O F VIN YL*L,2 ,3 *TRIAZ01ESS 87
TRIAZOLE DERIVATIVE LIGANDS FOR C OORDINATION C HEM ISTRY 88
TETRAZOLE SYNTHESIS 88
SYNTHESIS O F CHIRAL TRIAZOLES 88
SYNTHESIS O F TRIAZOLES W ITH LUMINESCENT PROPERTIES 89
SYNTHESIS O F TRIAZOLE LIBRARIES 89
SYNTHESIS O F PHOSPHORYLATED TRIAZOLES 89
O THER L,3 **DIPOLAR CYCLOADDITIONS 90
A TOM ECONOMY AND S IM PLICITY O F PROCEDURES IN M ULTICOM PONENT
REACTIONS 90
REACTION CONDITIONS 91
COPPER COMPOUNDS AS CATALYSTS 91
COPPER COMPLEXES W ITH N ITROGEN- AND PHOSPHOROUS-DONATING
LIGANDS 91
IM M OBILIZED COPPER SPECIES 91
COPPER NANOCATALYSIS 92
SUMMARY AND CONCLUSIONS 92
REFERENCES 93
SYNTHESIS OF SUBSTITUTED 1,2,3-TRIAZOLES THROUGH ORGANOCATALYSIS 99
KENGADARANEANEBOUSELVYANDDHEVALAPALLYB. RAMOCHARY
IN TRO D U CTIO N 99
PREFORMED*ENOLATE*BASED SYNTHESIS O F SUBSTITUTED
L,2,3-TRIAZOLES 101
2.3.8.2 A N EFFICIENT SYNTHESIS O F RUFINAMIDE 68
2.3.8.3 C ONTINUOUS-FLOW TOTAL SYNTHESIS O F RUFINAMIDE 68
REFERENCES 70
1
2
1
1
1
1
2
2
2
2
3
3
3
3
3
3
H
2
4.
*
4
* .
PREFORMED*ENAMINE*BASED SYNTHESIS O F SUBSTITUTED
L,2 ,3 *TRIAZOLES 106
SYNTHESIS O F SUBSTITUTED 1,2,3-TRIAZOLES VIA CATALYTIC ENOLATE
INTERMEDIATES 109
GENERAL M ECHANISTIC ASPECTS O F ENOLATE ROUTE 113
SYNTHESIS O F SUBSTITUTED L,2 ,3 *TRIAZOLES VIA ENAMINE
INTERMEDIATES 114
GENERAL M ECHANISTIC ASPECTS O F ENAMINE ROUTE 123
SYNTHESIS O F SUBSTITUTED 1,2,3-TRIAZOLES VIA IM IN IU M
INTERM EDIATE 123
MISCELLANEOUS ROUTES FO R THE SYNTHESIS O F 1,2,3-TRIAZOLES 124
CONCLUSIONS 136
ACKNOWLEDGMENTS 136
REFERENCES 137
APPLICATIONS OF THE CU-CATALYZED AZIDE-ALKYNE CYCLOADDITION (CUAAC)
IN PEPTIDES 141
FREEK A. B. NA. HOOGSTEDE AND F*
0
NS P. J.T. RUTJES
IN TRO D U CTIO N 141
C UAAC -M EDIATED PEPTIDE CONJUGATION STRATEGIES 142
C UAAC -M EDIATED PEPTIDE BACKBONE M O D IFICA TIO N STRATEGIES 148
CONCLUSIONS 157
REFERENCES 157
SYNTHESIS OF DIVERSE CARBOHYDRATE-BASED MOLECULES USING CLICK
CHEMISTRY 161
ANOOP 5. SINGH/ KUNJ B. MISHSO/ AMRITO MISHRA, AND VINOD K. TIWORI
IN TRO D U CTIO N 1* 1
CU-CATALYZED C LICK C HEM ISTRY IN THE SYNTHESIS O F DIVERSE
GLYCOCONJUGATES 162
SYNTHESIS O F CARBOHYDRATE-BASED SIMPLE TO COMPLEX
MACROCYCLES 181
C LICK-INSPIRED SYNTHESIS OR DIVERSE NEOGLYCOCONJUGATES 185
CONCLUSION AND FUTURE PERSPECTIVE 195
ACKNOWLEDGM ENT 196
REFERENCES 196
AZIDE-ALKYNE CLICK REACTION *N POLYMER SCIENCE 203
JOYDEB IN D A L AND * . RAMAKRISHNAN
IN TRO D U CTIO N 203
LINEAR, D ENDRITIC, AND HYPERBRANCHED POLYMERS 205
TELECHELIC AND BLOCK COPOLYMERS 220
STAR AND STAR-BLOCK POLYMERS 226
CYCLIC POLYMERS 230
SIDE-CHAIN CLICKABLE POLYMERS 235
I
O
3
4
5
6
7
8
.9
.1
*
1
2
3
4
*
H
2
3
4
5
1
2
3
4
5
6
4.
4
4
4
4.
4
4
4
5
U
S
5
5
5
6
6
6
6
6
6
7
7
7
7
7
*
7.
7.
7.7
7.8
7*
7.10
7.11
7.12
8
8.1
8.2
8
.
2.1
8
.
2.2
8.2.3
8.2.4
8.2.5
8
.
2.6
8.3
Q
*-*
9.1.1
9.1.2
9.1.3
9.1.4
* 9
10
10.1
10
.
1.1
10
.
1
.
1.1
10
.
1
.
1.2
10.2
CROSS-LINKED POLYMERIC SYSTEMS 238
POROUS ORGANIC POLYMERS 242
SURFACE M ODIFICATION USING C UAAC REACTION 244
STRAIN-PROM OTED C LICK REACTION 247
TOPOCHEMICAL A Z ID E -A LK Y N E C YCLOADDITION (TAAC )
REACTIONS 249
SUMMARY AND O UTLOOK 251
REFERENCES 251
THIOL-BASED *CLICK* CHEMISTRY FOR MACROMOLECULAR ARCHITECTURE
DESV^** 2* *
WEIDONG ZHANG, KU** CHEN, AND GAOPAN CHEN
IN TRO D U CTIO N 255
IH IO L C HEM ISTRY FO R M ACROM OLECULAR A RCHITECTURE DESIGN 256
LINEAR POLYMERS 256
G RAFT AND COMB POLYMERS 258
STAR POLYMERS 261
CYCLIC POLYMERS 263
D ENDRITIC AND HYPERBRANCHEA POLYMERS 265
CONJUGATED AND H YBRID POLYMERS 270
CONCLUSION 276
ACKNOWLEDGMENTS 284
REFERENCES 284
SYNTHESIS OF MACROCYCLES AND CLICK CHEMISTRY 287
DARIO PASINI
IN TRO D U CTIO N 287
PEPTIDE- AND SUGAR-CONTAINING C LICK MACROCYCLES 289
C LICK MACROCYCLES FOR A N IO N BINDING AND SUPRAMOLECULAR
RECOGNITION 297
C LICKING MACROCYCLES TO FORM MECHANICAL BONDS 300
CYCLIC POLYMERS OBTAINED BY THE C UAAC C LICK REACTION 302
SUMMARY AND CONCLUSIONS 304
REFERENCES 304
MODIFICATIONS OF NUCLEOSIDES, NUCLEOTIDES, AND NUCLEIC ACIDS USING
HU*SGENS [3+2] AZIDE-ALKYNE CYDOADDITION: OPENING PANDORA S
ROY 309
FRANCKAMBLARD, OZKAN SARI/ SEBASTIEN BOUCLE, AHMED KHALIL, AND RAYMOND
F. SCHINAZL
IN TRO D U CTIO N
309
NUCLEOSIDE M ODIFICATIONS 309
NUCLEOSIDE ANALOGS AS POTENTIAL DRUGS 309
NUCLEOSIDE BIOCONJUGATES 311
NUCLEOTIDE AND NUCLEIC A CID M ODIFICATIONS 316
10.2.1 *A RTIFIC IA L* D N A
10.2.2 PRESYNTHETIC M ODIFICA TIO N D N A 316
10.2.3 POSTSYNTHETIC M OD IFICA TIO N 318
10.3 CONCLUSION 331
ACKNOWLEDGMENTS 332
REFERENCES 332
INDEX 337
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| indexdate | 2024-07-10T07:33:34Z |
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| isbn | 9783527339167 9783527694174 |
| language | English |
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| publisher | Wiley-VCH Verlag GmbH & Co. KGaA |
| record_format | marc |
| spelling | Click reactions in organic synthesis edited by Srinivasan Chandrasekaran Weinheim Wiley-VCH Verlag GmbH & Co. KGaA [2016] © 2016 XVI, 341 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier Click-Chemie (DE-588)7700321-4 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Click-Chemie (DE-588)7700321-4 s DE-604 Chandrasekaran, Srinivasan 1945- (DE-588)1111818649 edt Erscheint auch als Online-Ausgabe, EPUB 978-3-527-69418-1 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-69416-7 Erscheint auch als Online-Ausgabe, PDF 978-3-527-69415-0 http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-33916-7/ Verlag DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029140377&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Click reactions in organic synthesis Click-Chemie (DE-588)7700321-4 gnd |
| subject_GND | (DE-588)7700321-4 (DE-588)4143413-4 |
| title | Click reactions in organic synthesis |
| title_auth | Click reactions in organic synthesis |
| title_exact_search | Click reactions in organic synthesis |
| title_full | Click reactions in organic synthesis edited by Srinivasan Chandrasekaran |
| title_fullStr | Click reactions in organic synthesis edited by Srinivasan Chandrasekaran |
| title_full_unstemmed | Click reactions in organic synthesis edited by Srinivasan Chandrasekaran |
| title_short | Click reactions in organic synthesis |
| title_sort | click reactions in organic synthesis |
| topic | Click-Chemie (DE-588)7700321-4 gnd |
| topic_facet | Click-Chemie Aufsatzsammlung |
| url | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-33916-7/ http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=029140377&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT chandrasekaransrinivasan clickreactionsinorganicsynthesis |