Perilithiation and the synthesis of 8-substituted-1-naphthamides

被引：52

作者：

Clayden, J

Frampton, CS

McCarthy, C

Westlund, N

机构：

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

[2] Roche Discovery Welwyn, Welwyn Garden City AL7 3AY, Herts, England

来源：

TETRAHEDRON | 1999年 / 55卷 / 49期

关键词：

amides; lithiation; naphthalenes; Polonoski reaction;

D O I：

10.1016/S0040-4020(99)00881-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing l-substituents such as -NMe2 or -CH2NMe2 allows the synthesis of 8-substituted-1-naphthamides. The 8-CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

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收藏

页码：14161 / 14184

页数：24

相关论文

共 57 条

[1] Barriers to rotation about the chiral axis of tertiary aromatic amides [J].

Ahmed, A ;

Bragg, RA ;

Clayden, J ;

Lai, LW ;

McCarthy, C ;

Pink, JH ;

Westlund, N ;

Yasin, SA .

TETRAHEDRON, 1998, 54 (43) :13277-13294

[2] Dearomatising cyclisations of lithiated N-benzylbenzamides [J].

Ahmed, A ;

Clayden, J ;

Yasin, SA .

CHEMICAL COMMUNICATIONS, 1999, (03) :231-232

[3] 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

[4]

Ahmed A. S. H, UNPUB

[5] CHEMISTRY OF 8-SUBSTITUTED 1-NAPHTHYLMETHYLENES AND 2-SUBSTITUTED BENZYLIDENES - A SIMPLE ENTRY TO 1H-CYCLOBUTA[DE]NAPHTHALENES [J].

BAILEY, RJ ;

CARD, PJ ;

SHECHTER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (19) :6096-6103

[6] TRIANIONS BY REGIOSELECTIVE AND STEREOSELECTIVE LITHIATION OF DIALLYLAMINES AND STRUCTURALLY RELATED-COMPOUNDS - SYNTHETIC APPLICATIONS [J].

BARLUENGA, J ;

GONZALEZ, R ;

FANANAS, FJ ;

YUS, M ;

FOUBELO, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08) :1069-1077

[7] METALATION OF METHOXYNAPHTHALENES [J].

BARNES, RA ;

NEHMSMAN.LJ .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (06) :1939-&

[8] DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS [J].

BEAK, P ;

SNIECKUS, V .

ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) :306-312

[9] DIRECTED LITHIATIONS - THE EFFECT OF VARYING DIRECTING GROUP ORIENTATION ON COMPETITIVE EFFICIENCIES FOR A SERIES OF TERTIARY AMIDE, SECONDARY AMIDE, AND ALKOXIDE DIRECTED ORTHO LITHIATIONS [J].

BEAK, P ;

KERRICK, ST ;

GALLAGHER, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :10628-10636

[10] ORTHO LITHIATION OF TERTIARY BENZAMIDES [J].

BEAK, P ;

BROWN, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (10) :1823-1824

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