Zincation of heterocycles and aryl nonaflates: directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
2012
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| Schlagworte: | |
| Online-Zugang: | Volltext http://d-nb.info/1025821947/34 https://nbn-resolving.org/urn:nbn:de:bvb:19-147520 Inhaltsverzeichnis |
| Beschreibung: | 194 Bl. graph. Darst. |
Internformat
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| 100 | 1 | |a Monzón Díaz, Gabriel Andrés |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Zincation of heterocycles and aryl nonaflates |b directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts |c Gabriel Andrés Monzón Díaz |
| 264 | 1 | |c 2012 | |
| 300 | |a 194 Bl. |b graph. Darst. | ||
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| 502 | |a München, Univ., Diss., 2012 | ||
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Datensatz im Suchindex
| _version_ | 1804149592937201664 |
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| adam_text | IMAGE 1
TABLE OF CONTENTS
A . I N T R O D U C T I O N 3
1. O V E R V I E W 4
2 . P R E P A R A T I O N O F O R G A N O M E T A L L I C R E A G E N T
S 5
2.1. HALOGEN-METAL EXCHANGE 5
2.2. OXIDATIVE INSERTION 7
2.3. DIRECTED METALATION 9
2.4. CROSS-COUPLING REACTIONS O F ORGANOMETALLICS 12
2.5. METALATION O F AROMATIC ANILINES 13
4 . O B J E C T I V E S 1 6
4.1. ZINCATION O F SENSITIVE AROMATICS AND HETEROAROMATICS . * 16
4.2. PREPARATION O F POLYFUNCTIONAL ORGANOMETALLICS VIA ORTHO-METALATION
16
4.3. METALATION O F ARYL NONAFLATES 17
4.4. METALATION O F PROTECTED ANILINES AND AMINO N-HETEROCYCLES 17
4.5. ZINC INSERTION IN BENZYL HETEROCYCLES 17
4.6. PREPARATION O F TERTIARY BENZYL AND PHENETYL AMINES 18
B . R E S U L T S A N D D I S C U S S I O N 1 9
1. R E G I O - A N D C H E M O S E L E C T I V E Z I N C A T I O N O F F
U N C T I O N A L I Z E D A R O M A T I C S A N D H E T E R O A R O M A
T I C S US ING
T M P Z N C L L I C L A N D M I C R O W A V E IRRADIATION 2 0
1.1. INTRODUCTI ON 20
1.2. ZINCATION O F POORLY ACTIVATED SUBSTRATES WITH TMPZNCLLICL UNDER
MICROWAVE IRRADIATION 21
1.3. SCALEABLE PREPARATION O F SENSITIVE FUNCTIONALIZED AROMATICS AND
HETEROAROMATICS USING
TMPZNCLLICL 24
2 . EFFICIENT P R E P A R A T I O N O F P O L Y F U N C T I O N A L O R
G A N O M E T A L L I C S VIA D I R E C T E D O 7 7 / O - M E T A L A
T I O N
WITH T M P - B A S E S OF M N , F E A N D L A 2 6
2.1. INTRODUCTION 26
2.2. SCALEABLE PREPARATION O F ORGANOMETALLICS WITH TMP-BASES O F MN, FE
AND LA 26
3 . D I R E C T E D O R T H O - A N D A/CTX-MAGNESIATION O R Z I N C A T
I O N OF P O L Y F U N C T I O N A L A R Y L N O N A F L A T E S .... 2
9
3.1. INTRODUCTION 29
3.2. FORMAL ORTHO- AND META-FUNCTIONALIZATIONS 29
3.3. FURTHER FUNTIONALIZATIONS O F POLYFUNCTIONAL ARYL NONAFLATES 35
4 . D I R E C T E D O R T H O - A N D M E 7 X - M A G N E S I A T I O N
O F F U N C T I O N A L I Z E D A N I L I N E S A N D A M I N O - S U B
S T I T U T E D
PYRIDINES A N D P Y R A Z I N E S 3 7
4.1. INTRODUCTION 37
4.2. DIRECTED ORTHO-METALATION 41
4.3. DIRECTED ORTHO-FUNCTIONALIZATIONS O F HETEROARYL AMINES 50
4.4. APPLICATION TO THE SYNTHESIS O F BIOLOGICALLY ACTIVE COMPOUNDS 52
HTTP://D-NB.INFO/1026390567
IMAGE 2
5 . P R E P A R A T I O N A N D R E A C T I O N S O F H E T E R O A R O
M A T I C B E N Z Y L Z I N C R E A G E N T S 5 3
5.1. INTRODUCTION 53
5.2. SYNTHESIS O F HETEROCYCLIC BENZYL AMINES 54
5.3. SYNTHESIS O F HETEROCYCLIC BENZYL CHLORIDES 57
5.4. PREPARATION AND REACTIONS O F HETEROBENZYL ZINC REAGENTS 58
5.5. PREPARATION O F HIGHLY FUNCTIONALIZED FUSED HETEROCYCLES 60
5.6. APPLICATION TO THE SYNTHESIS O F BIOLOGICALLY ACTIVE COMPOUNDS 64
6 . P R E P A R A T I O N OF T E R T I A R Y B E N Z Y L A N D P H E N E
T H Y L A M I N E S 6 6
6.1. INTRODUCTION 66
6.2. PREPARATION O F TERTIARY BENZYL AND PHENETHYL AMINES 67
4 . S U M M A R Y A N D O U T L O O K 6 9
4.1. REGIO- AND CHEMOSELECTIVE ZINCATION O F FUNCTIONALIZED AROMATICS
AND AND HETEROAROMATICS USING
TMPZNCLLICL AND MICROWAVE IRRADIATION 69
4.2. EFFICIENT PREPARATION O F POLYFUNCTIONAL ORGANOMETALLICS VIA
DIRECTED ORTHO-METALATION WITH TMPBASES O F MN, FE AND LA 70
4.3. DIRECTED ORTHO- AND META-MAGNESIATION OR ZINCATION O F
POLYFUNCTIONAL ARYL NONAFLATES 71
4.4. DIRECTED ORTHO- AND META-MAGNESIATION O F FUNCTIONALIZED ANILINES
AND AMINO-SUBSTITUTED PYRIDINES
AND PYRAZINES 72
4.5. PREPARATION AND REACTIONS O F HETEROAROMATIC BENZYL ZINC REAGENTS
74
4.6. PREPARATION O F TERTIARY BENZYL AND PHENETHYL AMINES 76
C . E X P E R I M E N T A L S E C T I O N 7 7
1. G E N E R A L C O N S I D E R A T I O N S 7 8
1.1. SOLVENTS 78
1.2. REAGENTS 79
1.3. CONTENT DETERMINATION O F ORGANOMETALLIC REAGENTS 80
1.4. CHROMATOGRAPHY : 80
1.5. ANALYTICAL DATA 80
2 . T Y P I C A L P R O C E D U R E S 8 2
2.1. TYPICAL PROCEDURE F O R THE METALATION OFPOLYFUNCTIONAL AROMATICS
AND HETEROAROMATICS WITH
TMPZNCL LICL (TP1) 82
2.2. TYPICAL PROCEDURE F O R THE METALATION O F POLYFUNCTIONAL AROMATICS
AND HETEROAROMATICS WITH
TMPZNCL LICL UNDER CONVENTIONAL HEATING OR MICROWAVE IRRADIATION (TP2)
82
2.3. TYPICAL PROCEDURE F O R THE METALATION O F POLYFUNCTIONAL AROMATICS
AND HETEROAROMATICS WITH
TMP 2 ZN 2MGCU 2LICL (TP3) 83
2.4. TYPICAL PROCEDURE F O R THE METALATION O F POLYFUNCTIONAL AROMATICS
AND HETEROAROMATICS WITH
TMPMGCL LICL (TP4) * . 83
2.5. TYPICAL PROCEDURE F O R THE METALATION OFPOLYFUNCTIONAL AROMATICS
AND HETEROAROMATICS WITH
TMP,MN-2MGCH 41.ICL (TPS) 83
IMAGE 3
2.6. TYPICAL PROCEDURE F O R THE METALATION OFPOLYFUNCTIONAL AROMATICS
AND HETEROAROMATICS WITH
TMP 2 FE-2MGCL 2 -4LICL (TP6) 84
2.7. TYPICAL PROCEDURE F O R THE METALATION OFPOLYFUNCTIONAL AROMATICS
AND HETEROAROMATICS WITH
TMPJ.A-3MFICLR5I.ICL (TP7) 84
2.8. TYPICAL PROCEDURE F O R THE SYNTHESIS O F AROMATIC AND
HETEROAROMATIC TRIFLUOROACETAMIDES F R O M
AROMATIC AND HETEROAROMATIC AMINES (TP8) 85
2.9. TYPICAL PROCEDURE F O R THE METALATION OFPOLYFUNCTIONAL AROMATIC A
N D HETEROAROMATIC
TRIFLUOROACETAMIDES WITH TMPMGCLLICL OR TMP 2 MG-2LICL (TP9) 85
2.10. TYPICAL PROCEDURE F O R PD-CATALYZED CROSS-CUPLING REACTIONS O F
METALATED TRIFLUOROACETAMIDES (TP 10)
86
2.11. TYPICAL PROCEDURE F O R ACYLATION REACTIONS O F METALATED
TRIFLUOROACETAMIDES (TP11) 86
2.12. TYPICAL PROCEDURE F O R ALLYLATION REACTIONS O F METALATED
TRIFLUOROACETAMIDES (TP 12) 86
2.13. TYPICAL PROCEDURE F O R THE PREPARATION O F (DIMETHYLAMINO)METHYL
HETEROARENES USING N,N,N ,N TETRAMETHYLMETHANEDIAMINE (TP 13) 87
2.14. TYPICAL PROCEDURE F O R THE PREPARATION O F HETEROAROMATIC BENZYL
CHLORIDES F R O M
(DIMETHYLAMINO)METHYL HETEROARENES (TP 14) 87
2.15. TYPICAL PROCEDURE F O R THE PREPARATION O F HETEROAROMATIC BENZYL
ZINC CHLORIDES BY LICL-PROMOTED
DIRECT ZINC INSERTION (TP 15) 88
2.16. TYPICAL PROCEDURE F O R THE PREPARATION O F DIARYLMETHANES BY THE
PD-CATALYZED CROSS-COUPLING OF
HETEROBENZYL ZINC CHLORIDES (TP 16) 88
2.17. TYPICAL PROCEDURE F O R THE PREPARATION O F HETEROPHENETHYLIC
ALCOHOLS BY THE REACTION O F HETEROBENZYL
ZINC CHLORIDES WITH ALDEHYDES (TP 17) 89
2.18. TYPICAL PROCEDURE F O R THE PREPARATION O F HETEROBENZYL KETONES
BY THE REACTION O F HETEROBENZYLIC ZINC
CHLORIDES WITH CARBOXYLIC ACID CHLORIDES (TP 18) 89
2.19. TYPICAL PROCEDURE F O R THE PREPARATION O F TERTIARY BENZYL AND
PHENETHYL AMINES (TP 19) 89
3. P R O D U C T S Y N T H E S I S A N D A N A L Y T I C A L D A T A 9 1
3.1. REGIO- AND CHEMOSELECTIVE ZINCATION O F FUNCTIONALIZED AROMATICS
AND HETEROAROMATICS USING
TMPZNCL LICL AND MICROWAVE IRRADIATION 91
3.2. PREPARATION O F POLYFUNCTIONAL ORGANOMETALLICS VIA DIRECTED
ORTHO-METALATION USING TMP-BASES OF
MN, FE AND LA 109
3.3. DIRECTED ORTHO- AND META-MAGNESIATION OR ZINCATION O F
POLYFUNCTIONAL ARYL NONAFLATES 114
3.4. DIRECTED ORTHO- AND META-MAGNESIATION O F POLYFUNCTIONAL N-ARYL AND
N-HETEROARYL
TRIFLUOROACETYLAMIDES 134
3.5. PREPARATION AND REACTIONS O F HETEROAROMATIC BENZYL ZINC COMPUNDS
159
3.6. PREPARATION O F TERTIARY BENZYL AND PHENETHYL AMINES 187
D . A P P E N D I X 1 9 0
L I S T OF A B B R E V I A T I O N S 1 9 1
C U R R I C U L U M V I T A E 1 9 3
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| spelling | Monzón Díaz, Gabriel Andrés Verfasser aut Zincation of heterocycles and aryl nonaflates directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts Gabriel Andrés Monzón Díaz 2012 194 Bl. graph. Darst. txt rdacontent n rdamedia nc rdacarrier München, Univ., Diss., 2012 (DE-588)4113937-9 Hochschulschrift gnd-content Erscheint auch als Online-Ausgabe urn:nbn:de:bvb:19-147520 http://edoc.ub.uni-muenchen.de/14752/ Verlag kostenfrei Volltext http://d-nb.info/1025821947/34 Langzeitarchivierung Nationalbibliothek https://nbn-resolving.org/urn:nbn:de:bvb:19-147520 Resolving-System DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025360968&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Monzón Díaz, Gabriel Andrés Zincation of heterocycles and aryl nonaflates directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts |
| subject_GND | (DE-588)4113937-9 |
| title | Zincation of heterocycles and aryl nonaflates directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts |
| title_auth | Zincation of heterocycles and aryl nonaflates directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts |
| title_exact_search | Zincation of heterocycles and aryl nonaflates directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts |
| title_full | Zincation of heterocycles and aryl nonaflates directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts Gabriel Andrés Monzón Díaz |
| title_fullStr | Zincation of heterocycles and aryl nonaflates directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts Gabriel Andrés Monzón Díaz |
| title_full_unstemmed | Zincation of heterocycles and aryl nonaflates directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts Gabriel Andrés Monzón Díaz |
| title_short | Zincation of heterocycles and aryl nonaflates |
| title_sort | zincation of heterocycles and aryl nonaflates directed magnesiation of highly substituted anilines and amino substituted heterocycles synthesis of heterobenzylic zinc compounds new generation of iminium salts |
| title_sub | directed magnesiation of highly substituted anilines and amino-substituted heterocycles ; synthesis of heterobenzylic zinc compounds ; new generation of iminium salts |
| topic_facet | Hochschulschrift |
| url | http://edoc.ub.uni-muenchen.de/14752/ http://d-nb.info/1025821947/34 https://nbn-resolving.org/urn:nbn:de:bvb:19-147520 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025360968&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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