One-Step Conversion of 2-Amino-N′-arylbenzamidines into 3-Aryl-4-imino-3, 4-dihydroquinazoline-2-carbonitriles Using 4, 5-Dichloro-1, 2, 3-dithiazolium Chloride

SI Mirallai, MJ Manos, PA Koutentis

Index: Mirallai, Styliana I.; Manos, Manolis J.; Koutentis, Panayiotis A. Journal of Organic Chemistry, 2013 , vol. 78, # 19 p. 9906 - 9913

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Citation Number: 11

Abstract

2-Amino-N′-arylbenzamidines react with 4, 5-dichloro-1, 2, 3-dithiazolium chloride (Appel salt) in the presence of Hünig's base (2 equiv) to give in one step 3-aryl-4-imino-3, 4- dihydroquinazoline-2-carbonitriles in 53–81% yields. Nine examples are presented along with the single-crystal X-ray structure of 4-imino-3-phenyl-3, 4-dihydroquinazoline-2- carbonitrile. Furthermore, the behavior of the latter toward both acid and base hydrolysis is ...

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