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Synthesis of 2,3-dihydro-1,3-thiazin-4(1H)- ones and their remarkably facile recyclization to 2,3-dihydropyrimidin-4(1H)-ones

✍ Scribed by Mykhaylo V. Vovk; Volodymyr A. Sukach; Alexander N. Chernega; Volodymyr V. Pyrozhenko; Andriy V. Bol'but;; Alexander M. Pinchuk

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 146 KB
Volume: 16
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.20129

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✦ Synopsis

Abstract

Functionalized 2,3‐dihydro‐1,3‐thiazin‐4(1H)‐one derivatives have been synthesized by cyclocondensation of 3‐alkyl(aryl)amino‐2‐cyano‐3‐mercaptoacrylamides with aldehydes and ketones under acidic catalysis. 6‐Alkyl(aryl)amino‐5‐cyano‐2,3‐dihy‐ dro‐1,3‐thiazin‐4(1H)‐ones, when treated with a dilute solution of potassium hydroxide, are converted into the potassium salts of isomeric compounds, 1‐alkyl‐ (aryl)‐5‐cyano‐6‐mercapto‐2,3‐dihydropyrimidin‐ 4(1H)‐ones. Alkylation of the latter with dimethyl sulfate in situ furnishes 1‐alkyl(aryl)‐6‐alkylthio‐5‐ cyano‐2,3‐dihydropyrimidin‐4(1H)‐ones, whereas boiling them in ethanol with an excess of hydrochloric acid leads to starting 2,3‐dihydro‐1,3‐thiazin‐4(1H)‐ones. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:426–436, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20129

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