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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.

Authors
  • Mirallai, Styliana I
  • Manos, Manolis J
  • Koutentis, Panayiotis A
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Oct 04, 2013
Volume
78
Issue
19
Pages
9906–9913
Identifiers
DOI: 10.1021/jo401648t
PMID: 24053152
Source
Medline
License
Unknown

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 investigated. All new compounds are fully characterized, and a mechanistic rationale for the formation of the iminoquinazolines is provided.

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