Tetrahedron Letters

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

J Azizian, M Mehrdad, K Jadidi, Y Sarrafi

Index: Azizian, Javad; Mehrdad, Morteza; Jadidi, Khosrow; Sarrafi, Yaghob Tetrahedron Letters, 2000 , vol. 41, # 27 p. 5265 - 5268

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Citation Number: 19

Abstract

Reaction of 3-arylimino-2-indolinones 1 with m-chloroperbenzoic acid in CH2Cl2 or methanol at 0° 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.

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