Reactivity of pyrido[4,3,2-kl]acridines:: Regioselective formation of 6-substituted derivatives

被引：18

作者：

Bouffier, L

Demeunynck, M

Milet, A

Dumy, P

机构：

[1] Univ Grenoble 1, LEDSS, UMR 5616, F-38041 Grenoble 9, France

[2] Univ Grenoble 1, ICMG, FR2607, F-38041 Grenoble 9, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 23期

关键词：

D O I：

10.1021/jo0487855

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyrido[4,3,2-kllacridines represent a new class of heterocycles, isomers of marine alkaloids. The 7H-pyrido[4,3,2-kl]acridine reacts as an electron rich heterocycle, and in particular via electrophilic substitution such as H/D exchange and the Vilsmeier-Haack reaction. The reaction is fully regioselective and gives the corresponding 6-substituted derivatives. The pyrido[4,3,2-kl]acridin-4-one reacts with amines and thiol, via 1,4-Michael addition to give the 6-amino or 6-thio analogues in a very efficient way. Molecular calculations account for the observed regioselectivity.

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页码：8144 / 8147

页数：4

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