Formation of Enehydrazine Intermediates through Coupling of Phenylhydrazines with Vinyl Halides: Entry into the Fischer Indole Synthesis

被引：63

作者：

Zhan, Fuxu ^{[1
,2
]}

Liang, Guangxin ^{[1
,2
]}

机构：

[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 04期

基金：

中国国家自然科学基金;

关键词：

C?N coupling; copper; heterocycles; natural products; synthetic methods; EFFICIENT COPPER CATALYST; PHYSOSTIGMINE ESERINE; ARYL HYDRAZIDES; N-ARYLATION; REARRANGEMENT REACTIONS; ASPIDOSPERMA ALKALOIDS; INDOLIZATION REACTION; DERIVATIVES; ROUTE; (+/-)-PHYSOSTIGMINE;

D O I：

10.1002/anie.201207173

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cut to the chase: Direct formation of an enehydrazine, an intermediate in the classic Fischer indole synthesis, solves the regioselectivity problem associated with indolization. This approach not only achieves selective synthesis of indoles through proper selection of the vinyl halide, but also leads to quick construction of desoxyeseroline and esermethole, as well as the key structural motif in the Akuammiline alkaloid vincorine. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1266 / 1269

页数：4

共 79 条

[1]

[Anonymous], ORG LETT

[2]

[Anonymous], BER DTSCH CHEM GES

[3]

[Anonymous], 2003, CHEM HETEROCYCLES ST, DOI DOI 10.1002/352760183X

[4]

[Anonymous], ANGEW CHEM

[5]

[Anonymous], 2012, ANGEW CHEM, DOI [DOI 10.1002/ANGE.201108970, 10.1002/anie.201108970]

[6] Palladium-catalyzed cross-coupling between vinyl halides and tert-butyl carbazate:: First general synthesis of the unusual N-Boc-N-alkenylhydrazines [J].

Barluenga, Jose ;

Moriel, Patricia ;

Aznar, Fernando ;

Valdes, Carlos .

ORGANIC LETTERS, 2007, 9 (02) :275-278

[7]

Blount BK, 1932, J CHEM SOC, P1429, DOI 10.1039/jr9320001429

[8] A novel access to tetrahydro-β-carbolines via one-pot hydroformylation/Fischer indlole synthesis:: Rearrangement of 3,3-spiroindoleninium cations [J].

Bondzic, Bojan P. ;

Eilbracht, Peter .

ORGANIC LETTERS, 2008, 10 (16) :3433-3436

[9] FUNCTIONALIZED 2-AZABICYCLO[3.3.1]NONANES .6. STUDIES DIRECTED TO THE SYNTHESIS OF PENTACYCLIC STRYCHNOS INDOLE ALKALOIDS [J].

BONJOCH, J ;

CASAMITJANA, N ;

QUIRANTE, J ;

RODRIGUEZ, M ;

BOSCH, J .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :267-275

[10] FURANO-IDOLINES AND PYRANO-IDOLINES - MODEL COMPOUNDS FOR INDOLE ALKALOID STUDIES [J].

BRITTEN, AZ ;

BARDSLEY, WG ;

HILL, CM .

TETRAHEDRON, 1971, 27 (22) :5631-&

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