Facile approach to diverse range of 1,3-diaza-heterocycles: angular/linear selectivity paradigm and a remarkable intramolecular methyl migration

被引：31

作者：

Kshirsagar, Umesh A. ^{[1
]}

Argade, Narshinha P. ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON | 2009年 / 65卷 / 27期

关键词：

AGENT BATRACYLIN;

D O I：

10.1016/j.tet.2009.04.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from cyclic anhydrides and tert-butyl 2-aminobenzylcarbamate, simple and efficient synthesis of diverse range of kinetically controlled angular and thermodynamically controlled linear tricyclic and tetracyclic 1,3-diaza-heterocycles have been described via the intramolecular cyclizations of the corresponding imides/anilic acid esters. The effect of imide stability on the angular/linear product selectivity has also been described. The kinetically controlled angular products were successfully transformed to the corresponding thermodynamically controlled linear products by refluxing in methanol or methanol and acetic acid mixture. An interesting in situ 1,2-intramolecular methyl group migration has also been described. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5244 / 5250

页数：7

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