Rearrangement of 4-imino-(1H,4H)-3,1-benzoxazine-2-ones to 2,4-quinazolinediones via an isocyanate carboxamide intermediate

被引：28
|
作者：
Azizian, J [1 ]
Mehrdad, M [1 ]
Jadidi, K [1 ]
Sarrafi, Y [1 ]
机构：
[1] Shahid Beheshti Univ, Fac Sci, Dept Chem, Tehran 19834, Iran
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 27期
关键词：
benzoxazines; carbamates; quinazolinones; rearrangements;
D O I：
10.1016/S0040-4039(00)00803-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of 3-arylimino-2-indolinones 1 with m-chloroperbenzoic acid in CH2Cl2 or methanol at 0 degrees C leads to the corresponding 3-aryl-2,4(1H,3H)-quinazolinediones 4 and (2-arylcarbamoyphenyl)carbamic acid methyl ester 5, respectively. These conversions proceed through 4-arylimino-(1H,4H)-3,1-benzoxazin-2-one 2 and its ring-opened isocyanate carboxamide isomer 3 as key intermediates. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5265 / 5268
页数：4
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