Dearomatising cyclisations of lithiated N-benzylbenzamides

被引：54

作者：

Ahmed, A ^{[1
]}

Clayden, J ^{[1
]}

Yasin, SA ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

CHEMICAL COMMUNICATIONS | 1999年 / 03期

关键词：

D O I：

10.1039/a808218i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

On treatment with (BuLi)-Li-t in the presence of HMPA, N-benzylbenzamides undergo anionic cyclisation with dearomatisation to give an extended amide enolate which reacts with electrophiles to yield bicyclic cyclohexadiene derivatives.

引用

页码：231 / 232

页数：2

共 23 条

[1] Anionic cyclisations of an N-benzyl naphthamide:: a route to benzo[e]isoindolones [J].

Ahmed, A ;

Clayden, J ;

Rowley, M .

CHEMICAL COMMUNICATIONS, 1998, (03) :297-298

[2] Anion translocation in organolithiums: A mechanism for the lithiation and cyclisation of tertiary naphthamides [J].

Ahmed, A ;

Clayden, J ;

Rowley, M .

TETRAHEDRON LETTERS, 1998, 39 (34) :6103-6106

[3] Additions to functionalized arenes with concurrent dearomatization [J].

Bach, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (07) :729-730

[4] Preparation of substituted indolines via anionic cyclization [J].

Bailey, WF ;

Jiang, XL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2596-2597

[5] DIPOLE-STABILIZED CARBANIONS - NOVEL AND USEFUL INTERMEDIATES [J].

BEAK, P ;

REITZ, DB .

CHEMICAL REVIEWS, 1978, 78 (03) :275-316

[6] Spirolactams by a novel ipso-radical cyclisation and loss of aromaticity [J].

Boivin, J ;

Yousfi, M ;

Zard, SZ .

TETRAHEDRON LETTERS, 1997, 38 (34) :5985-5988

[7] REDUCTIVE LITHIATION MEDIATED ANIONIC CYCLIZATIONS AND [2,3]-SIGMATROPIC REARRANGEMENTS [J].

BROKA, CA ;

SHEN, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2981-2984

[8] THE USE OF CYCLOHEXA-3,5-DIENE-1,2-DIOLS IN ENANTIOSPECIFIC SYNTHESIS [J].

CARLESS, HAJ .

TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :795-826

[9] Synthesis of 3-alkylpyrrolidines by anionic cyclization [J].

Coldham, I ;

Hufton, R .

TETRAHEDRON, 1996, 52 (38) :12541-12552

[10] Anionic cyclizations of alpha-aminoorganolithiums. Determination of the stereoselectivity at the carbanion center and the synthesis of (+)-pseudoheliotridane [J].

Coldham, I ;

Hufton, R ;

Snowden, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (22) :5322-5323

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