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A facile synthesis of 3-substituted 2-cyanoquinazolin-4(3H)-ones and 3-alkyl-2-cyanothieno[3,2-d]pyrimidin-4(3H)-ones via 1,2,3-dithiazoles

✍ Scribed by Hyi-Seung Lee; Yong-Goo Chang; Kyongtae Kim

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
669 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of methyl anthranilate with 4,5‐dichloro‐1,2,3‐dithiazolium chloride (Appel's salt) in the presence of pyridine (2 equivalents) in dichloromethane at room temperature gave methyl N‐(4‐chloro‐5__H__‐1,2,3‐dithiazol‐5‐ylidene)anthranilate (3a) (50% yield), which reacted with sterically less hindered primary alkylamines to give directly 3‐alkyl‐2‐cyanoquinazolin‐4(3__H__)‐ones 5 in moderate to good yields. With tert‐butylamine, N‐(2‐methoxycarbonylphenyl)iminocyanomethyl N‐(tert‐butyl) disulfide 7 and methyl 2‐(N‐cyanothioformamido)anthranilate (8) were isolated in 33% and 59% yields, respectively. The cyano group of quinazoline 5a (R = CH~3~) is readily displaced by various nucleophiles to give 2‐substituted quinazolinones 11–19, which indicates that compounds 5 can be utilized as starting materials for the synthesis of new 2‐substituted quinazolines. Similarly 3‐alkyl‐2‐cyanomieno[3,2,‐d]pyrimidin‐4(3__H)‐ones 22 were prepared from methyl 3‐[N‐(4‐chloro‐5__H‐1,2,3‐dimiazol‐5‐ylidene)]‐2‐thiophencarboxylate (21) in moderate to good yields.

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