Gallium(III)-Catalyzed Three-Component (4+3) Cycloaddition Reactions

被引：109

作者：

Han, Xinping ^{[1
]}

Li, Hui ^{[1
]}

Hughes, Russell P. ^{[1
]}

Wu, Jimmy ^{[1
]}

机构：

[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 41期

基金：

美国国家科学基金会;

关键词：

annulation; cycloaddition; heterocycles; gallium; multicomponent reactions; MOLECULAR-ORBITAL METHODS; PHOSPHOROTHIOATE ESTERS; DENSITY FUNCTIONALS; OXYALLYL CATIONS; BASIS-SETS; TRIFLATE; CORE; CONSTRUCTION; DERIVATIVES; ALKYLATION;

D O I：

10.1002/anie.201205238

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct approach to indoles: The title reaction generates cyclohepta[b]indole derivatives in a single step at room temperature (see scheme). Exclusion of air or moisture is not required. DFT calculations support a stepwise cyclization event, and the versatility of the method is demonstrated by providing quick access to a library of cyclohepta[b]indole analogues. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

收藏

页码：10390 / 10393

页数：4

相关论文

共 89 条

[41] A two step route to indoles from haloarenes-a versatile variation on the Fischer indole synthesis [J].

Inman, Martyn ;

Moody, Christopher J. .

CHEMICAL COMMUNICATIONS, 2011, 47 (02) :788-790

[42] A synthetic use of the intramolecular alkyl migration process in indolylborates for intramolecular cyclization: a novel construction of carbazole derivatives [J].

Ishikura, M ;

Kato, H .

TETRAHEDRON, 2002, 58 (49) :9827-9838

[43] Generation and Reactivity of Aza-Oxyallyl Cationic Intermediates: Aza-[4+3] Cycloaddition Reactions for Heterocycle Synthesis [J].

Jeffrey, Christopher S. ;

Barnes, Korry L. ;

Eickhoff, John A. ;

Carson, Christopher R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) :7688-7691

[44] New entries to water-compatible Lewis acids [J].

Kobayashi, Shu ;

Ogawa, Chikako .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (23) :5954-5960

[45] SELF-CONSISTENT MOLECULAR-ORBITAL METHODS .20. BASIS SET FOR CORRELATED WAVE-FUNCTIONS [J].

KRISHNAN, R ;

BINKLEY, JS ;

SEEGER, R ;

POPLE, JA .

JOURNAL OF CHEMICAL PHYSICS, 1980, 72 (01) :650-654

[46] Novel thiopyrano[3,2-b] and cycloalkeno[1,2-b]indole derivatives with high inhibitory properties in LTB4 production [J].

Kuehm-Caubère, C ;

Caubère, P ;

Jamart-Grégoire, B ;

Pfeiffer, B ;

Guardiola-Lemaître, P ;

Manechez, D ;

Renard, P .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (01) :51-61

[47] Cu(I)-Catalyzed, α-Selective, Allylic Alkylation Reactions between Phosphorothioate Esters and Organomagnesium Reagents [J].

Lauer, Andrew M. ;

Mahmud, Farzeen ;

Wu, Jimmy .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (23) :9119-9123

[48] Total synthesis of tropoloisoquinolines: Imerubrine, isoimerubrine, and grandirubrine [J].

Lee, JC ;

Cha, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (14) :3243-3246

[49] Total synthesis of (-)-colchicine by an oxyallyl [4+3] cycloaddition [J].

Lee, JC ;

Cha, JK .

TETRAHEDRON, 2000, 56 (52) :10175-10184

[50] Total synthesis of colchicine.: α-methoxy-substituted oxyallyl [4+3] cycloaddition approach [J].

Lee, JC ;

Jin, SJ ;

Cha, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2804-2805

← 1 2 3 4 5 6 7 8 9 →