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A facile synthesis of 2-substituted thieno[3′,2′-5,6]-pyrido[4,3-d]pyrimidin-4(3H)-ones

✍ Scribed by Jian-Chao Liu; Hong-Wu He; Qing-Yun Ren; Ming-Wu Ding

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
217 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image

The thienopyridine derivative 2, obtained from reaction of acetoacetic ester with 1 in the presence of tin tetrachloride, was treated with triphenylphosphine in hexachloroethane and Et~3~N to give iminophosphorane 3. Iminophosphorane 3 reacted with phenyl isocyanate to give carbodiimide 4, which was further treated with phenols or ethenol to produce 2‐substituted 5,8,9‐trimethyl‐3‐phenyl‐thieno[3′,2′‐5,6]pyrido[4,3‐d]pyrimidin‐4(3__H__)‐ones 5 in presence of catalytic amount of K~2~CO~3~ or EtONa. The structures of compounds 5 were confirmed by ^1^H NMR, IR, MS, and elemental analysis.

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## Abstract magnified image The carbodiimides **5**, obtained from reactions of iminophosphorane **4** with aromatic isocyanates, reacted with amines, phenols or ROH to give 2‐substituted 5,6,7,8‐tetrahydropyrido[4′,3′:4,5]thieno[2,3‐__d__]‐pyrimidin‐4(3__H__)‐one 7 in the presence of catalytic am