Unexpected regiospecific reactivity of a substituted phthalic anhydride

被引：25

作者：

Petersson, Maria J.

Marchal, Camille

Loughlin, Wendy A. ^{[1
]}

Jenkins, Ian D.

Healy, Peter C.

Almesaker, Ann

机构：

[1] Griffith Univ, Eskitis Inst, Sch Sci, Brisbane, Qld 4111, Australia

[2] Griffith Univ, Eskitis Inst, Nat Prod Discovery, Brisbane, Qld 4111, Australia

[3] Ecole Normale Super, Magistere Chim, F-75055 Paris, France

来源：

TETRAHEDRON | 2007年 / 63卷 / 06期

关键词：

(3-8) phthalic anhydride; nucleophilic addition; intramolecular ring closure; hydrobenzoindole;

D O I：

10.1016/j.tet.2006.11.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective nucleophilic addition at C1 of anhydride 7 by a range of nucleophiles occurs to produce amide, ester and thioester derivatives 8-15 (60-99%). The increased electrophilic reactivity of the C I carbonyl group of anhydride 7 is supported by a competition experiment with phthalic anhydride. Unexpected formation of lactams 18 and 19 from amides 12 and 13 was shown to proceed via the lactamols 16 and 17 and could be controlled by the reaction conditions. The solid-state structure of 19 is reported. (c) 2006 Published by Elsevier Ltd.

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收藏

页码：1395 / 1401

页数：7

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