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A facile one-pot regioselective synthesis of [1,2,4]triazolo[4,3-a]5(1H)-pyrimidinones via tandem Japp–Klingemann, Smiles rearrangement, and cyclization reactions

✍ Scribed by Ahmad S. Shawali; Magda A. Abdallah; Mosselhi A. N. Mosselhi; Thoraya A. Farghaly

Publisher: John Wiley and Sons
Year: 2002
Tongue: English
Weight: 137 KB
Volume: 13
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.10008

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✦ Synopsis

Abstract

Coupling of active [(4‐oxo‐6‐phenyl‐3__H__‐pyrimidin‐2‐yl)thio]methine compounds (3) with diazotized anilines in the presence of base gave [1,2,4]triazolo[4,3‐a]pyrimidines (7). The latter products were also obtained by reactions of hydrazonoyl chlorides (10) with either 6‐phenyl‐2‐thiouracil (1) or the 2‐methylthio derivative 9. The mechanisms and the regiochemistry of the reactions studied are discussed. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:136–140, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10008

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