Multicomponent reactions towards heterocycles: concepts and applications
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[2022]
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| Beschreibung: | xii, 604 Seiten Illustrationen |
| ISBN: | 9783527349081 3527349081 |
Internformat
MARC
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| 015 | |a 21,N33 |2 dnb | ||
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| 020 | |a 9783527349081 |c hbk. |9 978-3-527-34908-1 | ||
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| 084 | |a VK 7200 |0 (DE-625)147417:253 |2 rvk | ||
| 245 | 1 | 0 | |a Multicomponent reactions towards heterocycles |b concepts and applications |c edited by Erik V. Van der Eycken, Upendra K. Sharma |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c [2022] | |
| 264 | 4 | |c © 2022 | |
| 300 | |a xii, 604 Seiten |b Illustrationen | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 0 | 7 | |a Heterocyclische Verbindungen |0 (DE-588)4159726-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Eintopfreaktion |0 (DE-588)4254931-0 |2 gnd |9 rswk-swf |
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Industrial Chemistry | ||
| 653 | |a Methods - Synthesis & Techniques | ||
| 653 | |a Organische Chemie / Methoden, Synthesen, Verfahren | ||
| 653 | |a Pharmaceutical & Medicinal Chemistry | ||
| 653 | |a Pharmazeutische u. Medizinische Chemie | ||
| 653 | |a Technische u. Industrielle Chemie | ||
| 653 | |a CH30: Technische u. Industrielle Chemie | ||
| 653 | |a CH60: Pharmazeutische u. Medizinische Chemie | ||
| 653 | |a CH81: Organische Chemie / Methoden, Synthesen, Verfahren | ||
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
| 689 | 0 | 0 | |a Heterocyclische Verbindungen |0 (DE-588)4159726-6 |D s |
| 689 | 0 | 1 | |a Eintopfreaktion |0 (DE-588)4254931-0 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Van der Eycken, Erik V. |0 (DE-588)1164478362 |4 edt | |
| 700 | 1 | |a Sharma, Upendra K. |0 (DE-588)116447815X |4 edt | |
| 710 | 2 | |a Wiley-VCH |0 (DE-588)16179388-5 |4 pbl | |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, PDF |z 978-3-527-83242-2 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, EPUB |z 978-3-527-83244-6 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, OBOOK |z 978-3-527-83243-9 |
| 856 | 4 | 2 | |m X:MVB |u http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34908-1/ |3 Kurzbeschreibung |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033045007&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-033045007 | ||
Datensatz im Suchindex
| _version_ | 1804183130728300544 |
|---|---|
| adam_text | V
CONTENTS
PREFACE
XI
1
HETEROCYCLES
AS
INPUTS
IN
MCRS:
AN
UPDATE
1
OULDOUZ
GHASHGHAEI,
MARINA
PEDROLA,
CARMEN
ESCOLANO,
AND
RODOLFO
LAVILLA
1.1
INTRODUCTION
1
1.2
CONCERTED
MCRS
1
1.3
RADICAL
MCRS
11
1.4
METAL-CATALYZED
MCRS
16
1.5
CARBONYL/IMINE
POLAR
MCRS
19
1.6
ISOCYANIDE-BASED
MCRS
24
1.7
MISCELLANY
PROCESSES
33
1.8
CONCLUSION
36
ACKNOWLEDGMENT
40
REFERENCES
40
2
HETEROCYCLES
AND
MULTICOMPONENT
POLYMERIZATIONS
45
SUSAN
SIEBEN,
JORDY
M.
SAYA,
DEAN
JOHNSON,
AND
ROMANO
VA.
ORRU
2.1
INTRODUCTION
45
2.2
UGI-TYPE
MULTICOMPONENT
POLYMERIZATIONS
48
2.3
MANNICH-TYPE
MULTICOMPONENT
POLYMERIZATIONS
52
2.4
BIGINELLI-TYPE
MULTICOMPONENT
POLYMERIZATIONS
64
2.5
HANTZSCH-TYPE
MULTICOMPONENT
POLYMERIZATIONS
71
2.6
DEBUS-RADZISZEWSKI-TYPE
MULTICOMPONENT
POLYMERIZATIONS
73
2.7
OTHER
MULTICOMPONENT
POLYMERIZATIONS
76
2.7.1
THE
CU(I)-CATALYZED
MCP
OF
DIYNES,
AZIDES,
AND
CARBODIIMIDES/NITRILES
78
2.7.2
THE
PD-CATALYZED
MCP
OF
IMINES,
ACYL
CHLORIDES,
AND
N-SULFONYL
IMINES
78
2.7.3
THE
MERCAPTOACETIC
ACID
LOCKING
IMINE
REACTION
80
2.8
CONCLUSIONS
AND
OUTLOOK
83
REFERENCES
84
VI
CONTENTS
3
MULTICOMPONENT
REACTIONS
IN
MEDICINAL
CHEMISTRY
91
ZEFENG
WANG
AND
ALEXANDER
DOMLING
3.1
INTRODUCTION
91
3.1.1
EXAMPLE:
PROTEIN-PROTEIN
INTERACTION
P53-MDM2
94
3.2
SCAFFOLDS
AND
THE
CHEMICAL
SPACE
OF
MCR
108
3.2.1
MARKETED
AND
CLINICAL
STAGE
DRUGS
110
3.3
SOME
BIOPHARMACEUTICAL
APPLICATION
OF
MCR
121
3.3.1
COMPUTATIONAL
METHODS
OF
MCR
CHEMICAL
SPACE
SCREENING
122
3.4
CONCLUSION
127
REFERENCES
127
4
SOLID-PHASE
HETEROCYCLE
SYNTHESIS
USING
MULTICOMPONENT
REACTIONS
139
LEONARDO
G.
CEBALLOS,
DAYLIN
F.
PACHECO,
BERNHARD
WESTERMANN,
AND
DANIEL
G.
RIVERA
4.1
INTRODUCTION
139
4.2
SYNTHESIS
OF
FIVE-MEMBERED
RING
HETEROCYCLES
140
4.3
SYNTHESIS
OF
SIX-MEMBERED
RING
HETEROCYCLES
144
4.4
SYNTHESIS
OF
FUSED
HETEROCYCLIC
RING
SYSTEMS
147
4.5
SYNTHESIS
OF
HETEROCYCLES
ON
SOLID-SUPPORTED
AMINO
ACIDS
150
4.6
SOLID-PHASE
MULTICOMPONENT
CONSTRUCTION
OF
DNA-ENCODED
HETEROCYCLE
LIBRARIES
153
4.7
MISCELLANEOUS
SUPPORTS
FOR
MULTICOMPONENT
SYNTHESIS
OF
HETEROCYCLES
154
4.8
CONCLUSIONS
157
REFERENCES
157
5
GREEN
SYNTHESIS
OF
HETEROCYCLES
VIA
MCRS
163
WEI
ZHANG
5.1
INTRODUCTION
163
5.2
HIGH-ORDER
MCRS
164
5.3
CONSECUTIVE
MCRS
176
5.4
MCRS
FOLLOWED
BY
CYCLIZATION
REACTIONS
187
5.5
MCRS
FOLLOWED
BY
CYCLOADDITION
OR
ANNULATION
REACTIONS
200
5.6
CONCLUSION
AND
OUTLOOK
207
REFERENCES
207
6
THE
USE
OF
FLOW
CHEMISTRY
IN
THE
MULTICOMPONENT
SYNTHESIS
OF
HETEROCYCLES
211
CHIARA
LAMBRUSCHINI,
LISA
MONI,
AND
ANDREA
BASSO
6.1
INTRODUCTION
211
6.2
MULTICOMPONENT
REACTIONS
UNDER
STANDARD
FLOW
CONDITIONS
212
6.3
MULTICOMPONENT
REACTIONS
WITH
HAZARDOUS
REAGENTS
217
6.4
MULTICOMPONENT
REACTIONS
UNDER
SPECIAL
CONDITIONS
219
6.4.1
REACTIONS
WITH
MICROWAVE
OR
INDUCTIVE
HEATING
220
CONTENTS
VII
6.4.2
REACTIONS
WITH
ACTIVE
PACKED-BED
COLUMNS
223
6.4.3
REACTIONS
UNDER
OTHER
CONDITIONS
226
6.5
TELESCOPED
REACTIONS
229
6.6
CONCLUSIONS
233
REFERENCES
235
7
C-H
FUNCTIONALIZATION
AS
AN
IMPERATIVE
TOOL
TOWARD
MULTICOMPONENT
SYNTHESIS
AND
MODIFICATION
OF
HETEROCYCLES
239
ALEXEY
A.
FESTA
AND
LEONID
G.
VOSKRESSENSKY
7.1
INTRODUCTION
239
7.2
TRANSITION-METAL-INVOLVED
C-H
FUNCTIONALIZATION
240
7.2.1
MULTICOMPONENT
SYNTHESIS
OF
HETEROCYCLES
THROUGH
C-H
FUNCTIONALIZATION
240
7.3
TRANSITION-METAL-INVOLVED
C-H
FUNCTIONALIZATION
259
7.3.1
MULTICOMPONENT
C-H
FUNCTIONALIZATION
OF
HETEROCYCLES
259
7.3.1.1
C(SP
2
)-H
FUNCTIONALIZATION
259
7.3.1.2
C(SP
3
)-H
FUNCTIONALIZATION
267
7.4
TRANSITION-METAL-FREE
C-H
FUNCTIONALIZATION
269
7.4.1
MULTICOMPONENT
SYNTHESIS
OF
HETEROCYCLES
THROUGH
C-H-FUNCTIONALIZATION
269
7.4.2
MULTICOMPONENT
C-H
FUNCTIONALIZATION
OF
HETEROCYCLES
273
REFERENCES
277
8
MULTICOMPONENT-SWITCHED
REACTIONS
IN
SYNTHESIS
OF
HETEROCYCLES
287
VALENTYN
A.
CHEBANOV,
SERHIY
M.
DESENKO,
VICTORIA
V.
LIPSON,
AND
NIKOLAY
YU.
GOROBETS
REFERENCES
329
9
RECENT
APPLICATIONS
OF
MULTICOMPONENT
REACTIONS
TOWARD
HETEROCYCLIC
DRUG
DISCOVERY
339
NATHAN
BEDARD,
ALESSANDRA
FISTROVICH,
KEVIN
SCHOFIELD,
ARTHUR
SHAW,
AND
CHRISTOPHER
HULME
9.1
INTRODUCTION
339
9.2
MULTICOMPONENT
REACTIONS
339
9.3
THE
UGI
REACTION
340
9.3.1
THE
UGI
REACTION
USED
IN
NATURAL
PRODUCT
SYNTHESIS
343
9.3.2
THE
UGI
REACTION
IN
FDA-APPROVED
DRUGS
AND
DRUG
CANDIDATES
343
9.3.2.1
SYNTHESIS
OF
LIPITOR
USING
UGI
4CR
349
9.3.2.2
SYNTHESIS
OF
IVOSIDENIB
UTILIZING
UGI
4CR
349
9.3.3
RAPID
LEAD
OPTIMIZATION
WITH
UGI
4CR
349
9.4
THE
PASSERINI
REACTION
353
9.4.1
THE
PASSERINI
REACTION
IN
NATURAL
PRODUCTS
353
9.5
GROEBKE-BLACKBURN-BIENAYME
(GBB-3CR)
MCR
353
VIII
CONTENTS
9.6
9.7
9.7.1
9.7.2
9.8
9.8.1
9.8.2
9.8.3
9.9
9.9.1
GEWALD
(G-3CR)
REACTION
361
THE
HANTZSCH
DIHYDROPYRIDINE
(DHP)
SYNTHESIS
364
FDA-APPROVED
HANTZSCH
DIHYDROPYRIDINES
368
ANTI-BACTERIAL
HANTZSCH
DHPS
368
THE
BIGINELLI
REACTION
370
BIGINELLI
REACTIONS
AND
NATURAL
PRODUCTS
371
BIGINELLI
DHPMS
AS
CNS
AGENTS
371
BIGINELLI
PRODUCTS
ANTITUMOR
CAPABILITIES
371
VAN
LEUSEN
REACTION
379
TOSMIC-MEDIATED
CYCLIZATION
TOWARD
NITROGEN-CONTAINING
HETEROCYCLES
379
9.9.2
9.9.2.1
APPLICATIONS
OF
THE
VAN
LEUSEN
REACTION
383
SEQUENTIAL
ONE-POT
THREE-STEP
3C-VAN
LEUSEN
REACTION/DEPROTECTION/CYCLIZATION
383
9.9.2.2
9.9.2.3
9.9.3
9.9.3.1
9.9.3.2
9.9.3.3
9.9.3.4
9.9.3.5
SEQUENTIAL
VAN
LEUSEN
REACTION/STAUDINGER/AZA-WITTIG/CYCLIZATION
386
DNA-CONJUGATED
VAN
LEUSEN
REACTION
386
APPLICATIONS
OF
THE
VAN
LEUSEN
REACTION
IN
DRUG
DISCOVERY
388
PURINERGIC
P2X7
RECEPTOR
ANTAGONISTS
388
INDOLEAMINE
2,3-DIOXYGENASE
(IDO1)
INHIBITORS
391
DISRUPTORS
OF
P53/MDM2
PROTEIN-PROTEIN
INTERACTIONS
392
DISRUPTORS
OF
PCSK9/LDLR
PROTEIN-PROTEIN
INTERACTIONS
392
INHIBITORS
OF
TGF0R1
AS
IMMUNO-ONCOLOGY
THERAPEUTICS
397
REFERENCES
397
10
MULTICOMPONENT
SYNTHESES
OF
HETEROCYCLES
BY
CATALYTIC
GENERATION
OF
ALKYNOYL
INTERMEDIATES
411
JONAS
NIEDBALLA
AND
THOMAS
J
J.
MULLER
10.1
10.2
10.3
10.3.1
10.3.2
10.3.3
10.3.4
10.3.5
10.3.6
10.4
10.4.1
10.4.2
10.4.3
10.4.4
10.4.5
10.4.6
10.4.7
10.5
INTRODUCTION
411
CATALYTIC
GENERATION
OF
ALKYNONES
412
MULTICOMPONENT
SYNTHESES
OF
FIVE-MEMBERED
HETEROCYCLES
415
PYRAZOLINES
415
PYRAZOLES
416
ISOXAZOLES
420
TRIAZOLES
420
THIOPHENES
422
INDOLONES
424
MULTICOMPONENT
SYNTHESES
OF
SIX-MEMBERED
HETEROCYCLES
427
PYRANONES
427
PYRIDINES
427
PYRIMIDINES
429
OXAZABORININES
432
COUMARINES
432
QUINOLINES
435
QUINOXALINES
435
CONCLUSION
AND
OUTLOOK
442
REFERENCES
442
CONTENTS
IX
11
SYNTHESIS
OF
SATURATED
HETEROCYCLES
VIA
MULTICOMPONENT
REACTIONS
447
CARLOS
K.Z.
ANDRADE,
CARLOS
E.M.
SALVADOR,
THAISSA
P.F.
ROSALBA,
LUCI LIA
Z.A.
CORREA,
LUAN
A.
MARTINHO,
AND
YURI
R.B.
SOUSA
11.1
11.2
11.3
11.4
11.5
11.6
11.7
11.8
11.9
INTRODUCTION
447
THREE-MEMBERED
RING
HETEROCYCLES
447
FOUR-MEMBERED
RING
HETEROCYCLES
448
FIVE-MEMBERED
RING
HETEROCYCLES
449
SIX-MEMBERED
RING
HETEROCYCLES
456
SEVEN-MEMBERED
RING
HETEROCYCLES
462
MACROCYCLES
463
FUSED
HETEROCYCLES
464
SPIRO
HETEROCYCLES
482
REFERENCES
485
12
MULTICOMPONENT
REACTIONS
AND
ASYMMETRIC
CATALYSIS
493
MELODY
E.
BOETIUS
AND
EELCO
RUIJTER
12.1
12.2
12.2.1
12.2.2
12.2.2.1
12.2.2.2
12.2.2.3
12.2.2.4
12.2.3
12.2.4
12.3
12.3.1
INTRODUCTION
493
IMINE-BASED
MCRS
494
STRECKER
REACTION
494
MANNICH
REACTION
494
AZA-HENRY
REACTION
498
PETASIS
REACTION
498
AZA-DIELS-ALDER
VIA
MANNICH
REACTION
PATHWAY
500
[2
+
2
+
2]
-
CYCLOADDITION
504
HANTZSCH
REACTION
504
BIGINELLI
REACTION
506
MICHAEL
ADDITION-BASED
MCRS
509
OXA-MICHAEL/MICHAEL/MICHAEL/ALDOL
CONDENSATION
CASCADE
REACTIONS
509
12.3.2
12.3.3
12.4
12.4.1
12.4.1.1
12.4.1.2
12.4.2
12.4.3
12.5
KNOEVENAGEL-MICHAEL
CASCADE
REACTION
511
MICHAEL-HENRY
CASCADE
REACTION
514
ISOCYANIDE-BASED
MCRS
514
PASSERINI
REACTIONS
521
PASSERINI-TYPE
TWO-COMPONENT
REACTIONS
521
PASSERINI
THREE-COMPONENT
REACTION
522
ISOCYANIDE-BASED
[3
+
2]-CYCLOADDITION
525
UGI-TYPE
REACTIONS
525
CONCLUSION
529
REFERENCES
536
13
RECENT
TRENDS
IN
METAL-CATALYZED
MCRS
TOWARD
HETEROCYCLES
551
LILIA
FUENTES-MORALES
AND
LUIS
D.
MIRANDA
13.1
13.2
INTRODUCTION
551
FIVE-MEMBERED
HETEROCYCLES
WITH
ONE
HETEROATOM
552
CONTENTS
13.3
FIVE-MEMBERED
SYSTEMS
WITH
TWO
HETEROATOMS
558
13.4
FIVE-MEMBERED
SYSTEMS
WITH
THREE
HETEROATOMS
561
13.5
SIX-MEMBERED
HETEROCYCLES
WITH
ONE
HETEROATOM
AND
THEIR
BENZO-FUSED
DERIVATIVES
566
13.6
SIX-MEMBERED
O-HETEROCYCLES
AND
THEIR
BENZOFUSED
DERIVATIVES
571
13.7
FOUR-MEMBERED
N-HETEROCYCLES
AND
SEVEN-MEMBERED
BENZOFUSED
N-HETEROCYCLES
574
13.8
CONCLUSION
576
REFERENCES
576
INDEX
583
|
| adam_txt |
V
CONTENTS
PREFACE
XI
1
HETEROCYCLES
AS
INPUTS
IN
MCRS:
AN
UPDATE
1
OULDOUZ
GHASHGHAEI,
MARINA
PEDROLA,
CARMEN
ESCOLANO,
AND
RODOLFO
LAVILLA
1.1
INTRODUCTION
1
1.2
CONCERTED
MCRS
1
1.3
RADICAL
MCRS
11
1.4
METAL-CATALYZED
MCRS
16
1.5
CARBONYL/IMINE
POLAR
MCRS
19
1.6
ISOCYANIDE-BASED
MCRS
24
1.7
MISCELLANY
PROCESSES
33
1.8
CONCLUSION
36
ACKNOWLEDGMENT
40
REFERENCES
40
2
HETEROCYCLES
AND
MULTICOMPONENT
POLYMERIZATIONS
45
SUSAN
SIEBEN,
JORDY
M.
SAYA,
DEAN
JOHNSON,
AND
ROMANO
VA.
ORRU
2.1
INTRODUCTION
45
2.2
UGI-TYPE
MULTICOMPONENT
POLYMERIZATIONS
48
2.3
MANNICH-TYPE
MULTICOMPONENT
POLYMERIZATIONS
52
2.4
BIGINELLI-TYPE
MULTICOMPONENT
POLYMERIZATIONS
64
2.5
HANTZSCH-TYPE
MULTICOMPONENT
POLYMERIZATIONS
71
2.6
DEBUS-RADZISZEWSKI-TYPE
MULTICOMPONENT
POLYMERIZATIONS
73
2.7
OTHER
MULTICOMPONENT
POLYMERIZATIONS
76
2.7.1
THE
CU(I)-CATALYZED
MCP
OF
DIYNES,
AZIDES,
AND
CARBODIIMIDES/NITRILES
78
2.7.2
THE
PD-CATALYZED
MCP
OF
IMINES,
ACYL
CHLORIDES,
AND
N-SULFONYL
IMINES
78
2.7.3
THE
MERCAPTOACETIC
ACID
LOCKING
IMINE
REACTION
80
2.8
CONCLUSIONS
AND
OUTLOOK
83
REFERENCES
84
VI
CONTENTS
3
MULTICOMPONENT
REACTIONS
IN
MEDICINAL
CHEMISTRY
91
ZEFENG
WANG
AND
ALEXANDER
DOMLING
3.1
INTRODUCTION
91
3.1.1
EXAMPLE:
PROTEIN-PROTEIN
INTERACTION
P53-MDM2
94
3.2
SCAFFOLDS
AND
THE
CHEMICAL
SPACE
OF
MCR
108
3.2.1
MARKETED
AND
CLINICAL
STAGE
DRUGS
110
3.3
SOME
BIOPHARMACEUTICAL
APPLICATION
OF
MCR
121
3.3.1
COMPUTATIONAL
METHODS
OF
MCR
CHEMICAL
SPACE
SCREENING
122
3.4
CONCLUSION
127
REFERENCES
127
4
SOLID-PHASE
HETEROCYCLE
SYNTHESIS
USING
MULTICOMPONENT
REACTIONS
139
LEONARDO
G.
CEBALLOS,
DAYLIN
F.
PACHECO,
BERNHARD
WESTERMANN,
AND
DANIEL
G.
RIVERA
4.1
INTRODUCTION
139
4.2
SYNTHESIS
OF
FIVE-MEMBERED
RING
HETEROCYCLES
140
4.3
SYNTHESIS
OF
SIX-MEMBERED
RING
HETEROCYCLES
144
4.4
SYNTHESIS
OF
FUSED
HETEROCYCLIC
RING
SYSTEMS
147
4.5
SYNTHESIS
OF
HETEROCYCLES
ON
SOLID-SUPPORTED
AMINO
ACIDS
150
4.6
SOLID-PHASE
MULTICOMPONENT
CONSTRUCTION
OF
DNA-ENCODED
HETEROCYCLE
LIBRARIES
153
4.7
MISCELLANEOUS
SUPPORTS
FOR
MULTICOMPONENT
SYNTHESIS
OF
HETEROCYCLES
154
4.8
CONCLUSIONS
157
REFERENCES
157
5
GREEN
SYNTHESIS
OF
HETEROCYCLES
VIA
MCRS
163
WEI
ZHANG
5.1
INTRODUCTION
163
5.2
HIGH-ORDER
MCRS
164
5.3
CONSECUTIVE
MCRS
176
5.4
MCRS
FOLLOWED
BY
CYCLIZATION
REACTIONS
187
5.5
MCRS
FOLLOWED
BY
CYCLOADDITION
OR
ANNULATION
REACTIONS
200
5.6
CONCLUSION
AND
OUTLOOK
207
REFERENCES
207
6
THE
USE
OF
FLOW
CHEMISTRY
IN
THE
MULTICOMPONENT
SYNTHESIS
OF
HETEROCYCLES
211
CHIARA
LAMBRUSCHINI,
LISA
MONI,
AND
ANDREA
BASSO
6.1
INTRODUCTION
211
6.2
MULTICOMPONENT
REACTIONS
UNDER
STANDARD
FLOW
CONDITIONS
212
6.3
MULTICOMPONENT
REACTIONS
WITH
HAZARDOUS
REAGENTS
217
6.4
MULTICOMPONENT
REACTIONS
UNDER
SPECIAL
CONDITIONS
219
6.4.1
REACTIONS
WITH
MICROWAVE
OR
INDUCTIVE
HEATING
220
CONTENTS
VII
6.4.2
REACTIONS
WITH
ACTIVE
PACKED-BED
COLUMNS
223
6.4.3
REACTIONS
UNDER
OTHER
CONDITIONS
226
6.5
TELESCOPED
REACTIONS
229
6.6
CONCLUSIONS
233
REFERENCES
235
7
C-H
FUNCTIONALIZATION
AS
AN
IMPERATIVE
TOOL
TOWARD
MULTICOMPONENT
SYNTHESIS
AND
MODIFICATION
OF
HETEROCYCLES
239
ALEXEY
A.
FESTA
AND
LEONID
G.
VOSKRESSENSKY
7.1
INTRODUCTION
239
7.2
TRANSITION-METAL-INVOLVED
C-H
FUNCTIONALIZATION
240
7.2.1
MULTICOMPONENT
SYNTHESIS
OF
HETEROCYCLES
THROUGH
C-H
FUNCTIONALIZATION
240
7.3
TRANSITION-METAL-INVOLVED
C-H
FUNCTIONALIZATION
259
7.3.1
MULTICOMPONENT
C-H
FUNCTIONALIZATION
OF
HETEROCYCLES
259
7.3.1.1
C(SP
2
)-H
FUNCTIONALIZATION
259
7.3.1.2
C(SP
3
)-H
FUNCTIONALIZATION
267
7.4
TRANSITION-METAL-FREE
C-H
FUNCTIONALIZATION
269
7.4.1
MULTICOMPONENT
SYNTHESIS
OF
HETEROCYCLES
THROUGH
C-H-FUNCTIONALIZATION
269
7.4.2
MULTICOMPONENT
C-H
FUNCTIONALIZATION
OF
HETEROCYCLES
273
REFERENCES
277
8
MULTICOMPONENT-SWITCHED
REACTIONS
IN
SYNTHESIS
OF
HETEROCYCLES
287
VALENTYN
A.
CHEBANOV,
SERHIY
M.
DESENKO,
VICTORIA
V.
LIPSON,
AND
NIKOLAY
YU.
GOROBETS
REFERENCES
329
9
RECENT
APPLICATIONS
OF
MULTICOMPONENT
REACTIONS
TOWARD
HETEROCYCLIC
DRUG
DISCOVERY
339
NATHAN
BEDARD,
ALESSANDRA
FISTROVICH,
KEVIN
SCHOFIELD,
ARTHUR
SHAW,
AND
CHRISTOPHER
HULME
9.1
INTRODUCTION
339
9.2
MULTICOMPONENT
REACTIONS
339
9.3
THE
UGI
REACTION
340
9.3.1
THE
UGI
REACTION
USED
IN
NATURAL
PRODUCT
SYNTHESIS
343
9.3.2
THE
UGI
REACTION
IN
FDA-APPROVED
DRUGS
AND
DRUG
CANDIDATES
343
9.3.2.1
SYNTHESIS
OF
LIPITOR
USING
UGI
4CR
349
9.3.2.2
SYNTHESIS
OF
IVOSIDENIB
UTILIZING
UGI
4CR
349
9.3.3
RAPID
LEAD
OPTIMIZATION
WITH
UGI
4CR
349
9.4
THE
PASSERINI
REACTION
353
9.4.1
THE
PASSERINI
REACTION
IN
NATURAL
PRODUCTS
353
9.5
GROEBKE-BLACKBURN-BIENAYME
(GBB-3CR)
MCR
353
VIII
CONTENTS
9.6
9.7
9.7.1
9.7.2
9.8
9.8.1
9.8.2
9.8.3
9.9
9.9.1
GEWALD
(G-3CR)
REACTION
361
THE
HANTZSCH
DIHYDROPYRIDINE
(DHP)
SYNTHESIS
364
FDA-APPROVED
HANTZSCH
DIHYDROPYRIDINES
368
ANTI-BACTERIAL
HANTZSCH
DHPS
368
THE
BIGINELLI
REACTION
370
BIGINELLI
REACTIONS
AND
NATURAL
PRODUCTS
371
BIGINELLI
DHPMS
AS
CNS
AGENTS
371
BIGINELLI
PRODUCTS
ANTITUMOR
CAPABILITIES
371
VAN
LEUSEN
REACTION
379
TOSMIC-MEDIATED
CYCLIZATION
TOWARD
NITROGEN-CONTAINING
HETEROCYCLES
379
9.9.2
9.9.2.1
APPLICATIONS
OF
THE
VAN
LEUSEN
REACTION
383
SEQUENTIAL
ONE-POT
THREE-STEP
3C-VAN
LEUSEN
REACTION/DEPROTECTION/CYCLIZATION
383
9.9.2.2
9.9.2.3
9.9.3
9.9.3.1
9.9.3.2
9.9.3.3
9.9.3.4
9.9.3.5
SEQUENTIAL
VAN
LEUSEN
REACTION/STAUDINGER/AZA-WITTIG/CYCLIZATION
386
DNA-CONJUGATED
VAN
LEUSEN
REACTION
386
APPLICATIONS
OF
THE
VAN
LEUSEN
REACTION
IN
DRUG
DISCOVERY
388
PURINERGIC
P2X7
RECEPTOR
ANTAGONISTS
388
INDOLEAMINE
2,3-DIOXYGENASE
(IDO1)
INHIBITORS
391
DISRUPTORS
OF
P53/MDM2
PROTEIN-PROTEIN
INTERACTIONS
392
DISRUPTORS
OF
PCSK9/LDLR
PROTEIN-PROTEIN
INTERACTIONS
392
INHIBITORS
OF
TGF0R1
AS
IMMUNO-ONCOLOGY
THERAPEUTICS
397
REFERENCES
397
10
MULTICOMPONENT
SYNTHESES
OF
HETEROCYCLES
BY
CATALYTIC
GENERATION
OF
ALKYNOYL
INTERMEDIATES
411
JONAS
NIEDBALLA
AND
THOMAS
J
J.
MULLER
10.1
10.2
10.3
10.3.1
10.3.2
10.3.3
10.3.4
10.3.5
10.3.6
10.4
10.4.1
10.4.2
10.4.3
10.4.4
10.4.5
10.4.6
10.4.7
10.5
INTRODUCTION
411
CATALYTIC
GENERATION
OF
ALKYNONES
412
MULTICOMPONENT
SYNTHESES
OF
FIVE-MEMBERED
HETEROCYCLES
415
PYRAZOLINES
415
PYRAZOLES
416
ISOXAZOLES
420
TRIAZOLES
420
THIOPHENES
422
INDOLONES
424
MULTICOMPONENT
SYNTHESES
OF
SIX-MEMBERED
HETEROCYCLES
427
PYRANONES
427
PYRIDINES
427
PYRIMIDINES
429
OXAZABORININES
432
COUMARINES
432
QUINOLINES
435
QUINOXALINES
435
CONCLUSION
AND
OUTLOOK
442
REFERENCES
442
CONTENTS
IX
11
SYNTHESIS
OF
SATURATED
HETEROCYCLES
VIA
MULTICOMPONENT
REACTIONS
447
CARLOS
K.Z.
ANDRADE,
CARLOS
E.M.
SALVADOR,
THAISSA
P.F.
ROSALBA,
LUCI'LIA
Z.A.
CORREA,
LUAN
A.
MARTINHO,
AND
YURI
R.B.
SOUSA
11.1
11.2
11.3
11.4
11.5
11.6
11.7
11.8
11.9
INTRODUCTION
447
THREE-MEMBERED
RING
HETEROCYCLES
447
FOUR-MEMBERED
RING
HETEROCYCLES
448
FIVE-MEMBERED
RING
HETEROCYCLES
449
SIX-MEMBERED
RING
HETEROCYCLES
456
SEVEN-MEMBERED
RING
HETEROCYCLES
462
MACROCYCLES
463
FUSED
HETEROCYCLES
464
SPIRO
HETEROCYCLES
482
REFERENCES
485
12
MULTICOMPONENT
REACTIONS
AND
ASYMMETRIC
CATALYSIS
493
MELODY
E.
BOETIUS
AND
EELCO
RUIJTER
12.1
12.2
12.2.1
12.2.2
12.2.2.1
12.2.2.2
12.2.2.3
12.2.2.4
12.2.3
12.2.4
12.3
12.3.1
INTRODUCTION
493
IMINE-BASED
MCRS
494
STRECKER
REACTION
494
MANNICH
REACTION
494
AZA-HENRY
REACTION
498
PETASIS
REACTION
498
AZA-DIELS-ALDER
VIA
MANNICH
REACTION
PATHWAY
500
[2
+
2
+
2]
-
CYCLOADDITION
504
HANTZSCH
REACTION
504
BIGINELLI
REACTION
506
MICHAEL
ADDITION-BASED
MCRS
509
OXA-MICHAEL/MICHAEL/MICHAEL/ALDOL
CONDENSATION
CASCADE
REACTIONS
509
12.3.2
12.3.3
12.4
12.4.1
12.4.1.1
12.4.1.2
12.4.2
12.4.3
12.5
KNOEVENAGEL-MICHAEL
CASCADE
REACTION
511
MICHAEL-HENRY
CASCADE
REACTION
514
ISOCYANIDE-BASED
MCRS
514
PASSERINI
REACTIONS
521
PASSERINI-TYPE
TWO-COMPONENT
REACTIONS
521
PASSERINI
THREE-COMPONENT
REACTION
522
ISOCYANIDE-BASED
[3
+
2]-CYCLOADDITION
525
UGI-TYPE
REACTIONS
525
CONCLUSION
529
REFERENCES
536
13
RECENT
TRENDS
IN
METAL-CATALYZED
MCRS
TOWARD
HETEROCYCLES
551
LILIA
FUENTES-MORALES
AND
LUIS
D.
MIRANDA
13.1
13.2
INTRODUCTION
551
FIVE-MEMBERED
HETEROCYCLES
WITH
ONE
HETEROATOM
552
CONTENTS
13.3
FIVE-MEMBERED
SYSTEMS
WITH
TWO
HETEROATOMS
558
13.4
FIVE-MEMBERED
SYSTEMS
WITH
THREE
HETEROATOMS
561
13.5
SIX-MEMBERED
HETEROCYCLES
WITH
ONE
HETEROATOM
AND
THEIR
BENZO-FUSED
DERIVATIVES
566
13.6
SIX-MEMBERED
O-HETEROCYCLES
AND
THEIR
BENZOFUSED
DERIVATIVES
571
13.7
FOUR-MEMBERED
N-HETEROCYCLES
AND
SEVEN-MEMBERED
BENZOFUSED
N-HETEROCYCLES
574
13.8
CONCLUSION
576
REFERENCES
576
INDEX
583 |
| any_adam_object | 1 |
| any_adam_object_boolean | 1 |
| author2 | Van der Eycken, Erik V. Sharma, Upendra K. |
| author2_role | edt edt |
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| author_facet | Van der Eycken, Erik V. Sharma, Upendra K. |
| building | Verbundindex |
| bvnumber | BV047660168 |
| classification_rvk | VK 7200 |
| ctrlnum | (OCoLC)1298891157 (DE-599)DNB1238911927 |
| discipline | Chemie / Pharmazie |
| discipline_str_mv | Chemie / Pharmazie |
| format | Book |
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| id | DE-604.BV047660168 |
| illustrated | Illustrated |
| index_date | 2024-07-03T18:52:17Z |
| indexdate | 2024-07-10T09:18:33Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
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| language | English |
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| physical | xii, 604 Seiten Illustrationen |
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| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Multicomponent reactions towards heterocycles concepts and applications edited by Erik V. Van der Eycken, Upendra K. Sharma Weinheim WILEY-VCH [2022] © 2022 xii, 604 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier Heterocyclische Verbindungen (DE-588)4159726-6 gnd rswk-swf Eintopfreaktion (DE-588)4254931-0 gnd rswk-swf Chemie Chemistry Industrial Chemistry Methods - Synthesis & Techniques Organische Chemie / Methoden, Synthesen, Verfahren Pharmaceutical & Medicinal Chemistry Pharmazeutische u. Medizinische Chemie Technische u. Industrielle Chemie CH30: Technische u. Industrielle Chemie CH60: Pharmazeutische u. Medizinische Chemie CH81: Organische Chemie / Methoden, Synthesen, Verfahren (DE-588)4143413-4 Aufsatzsammlung gnd-content Heterocyclische Verbindungen (DE-588)4159726-6 s Eintopfreaktion (DE-588)4254931-0 s DE-604 Van der Eycken, Erik V. (DE-588)1164478362 edt Sharma, Upendra K. (DE-588)116447815X edt Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-527-83242-2 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-83244-6 Erscheint auch als Online-Ausgabe, OBOOK 978-3-527-83243-9 X:MVB http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34908-1/ Kurzbeschreibung DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033045007&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Multicomponent reactions towards heterocycles concepts and applications Heterocyclische Verbindungen (DE-588)4159726-6 gnd Eintopfreaktion (DE-588)4254931-0 gnd |
| subject_GND | (DE-588)4159726-6 (DE-588)4254931-0 (DE-588)4143413-4 |
| title | Multicomponent reactions towards heterocycles concepts and applications |
| title_auth | Multicomponent reactions towards heterocycles concepts and applications |
| title_exact_search | Multicomponent reactions towards heterocycles concepts and applications |
| title_exact_search_txtP | Multicomponent reactions towards heterocycles concepts and applications |
| title_full | Multicomponent reactions towards heterocycles concepts and applications edited by Erik V. Van der Eycken, Upendra K. Sharma |
| title_fullStr | Multicomponent reactions towards heterocycles concepts and applications edited by Erik V. Van der Eycken, Upendra K. Sharma |
| title_full_unstemmed | Multicomponent reactions towards heterocycles concepts and applications edited by Erik V. Van der Eycken, Upendra K. Sharma |
| title_short | Multicomponent reactions towards heterocycles |
| title_sort | multicomponent reactions towards heterocycles concepts and applications |
| title_sub | concepts and applications |
| topic | Heterocyclische Verbindungen (DE-588)4159726-6 gnd Eintopfreaktion (DE-588)4254931-0 gnd |
| topic_facet | Heterocyclische Verbindungen Eintopfreaktion Aufsatzsammlung |
| url | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34908-1/ http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033045007&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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