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New domino-reaction for the synthesis of N4-(5-aryl-1,3-oxathiol-2-yliden)-2-phenylquinazolin-4-amines and 4-[4-aryl-5-(2-phenylquinazolin-4-yl)-1,3-thiazol-2-yl]morpholine

✍ Scribed by Walid Fathalla; Pavel Pazdera; Jaromír Marek

Publisher: Journal of Heterocyclic Chemistry
Year: 2002
Tongue: English
Weight: 68 KB
Volume: 39
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570390605

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✦ Synopsis

Abstract

The model morpholine‐1‐carbothioic acid (2‐phenyl‐3__H__‐quinazolin‐4‐ylidene) amide (1) reacts with phenacyl bromides to afford N^4^‐(5‐aryl‐1,3‐oxathiol‐2‐yliden)‐2‐phenylquinazolin‐4‐amines (4) or N^4^‐(4,5‐diphenyl‐1,3‐oxathiol‐2‐yliden)‐2‐phenyl‐4‐aminoquinazoline (5) by a thermodynamically controlled reversible reaction favoring the enolate intermediate, while the 4‐[4‐aryl‐5‐(2‐phenylquinazolin‐4‐yl)‐1,3‐thiazol‐2‐yl]morpholine (8) was produced by a kinetically controlled reaction favoring the C‐anion intermediate. ^1^H nmr, ^13^C nmr, ir, mass spectroscopy and x‐ray identified compounds (4), (5) and (8).

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