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Synthesis of 2-imino-7-methyl-2,3-dihydroimidazo[1,2-a]-pyrimidin-5(1H)-ones and their reactions with nucleophiles

✍ Scribed by Virginija Jakubkiene; Zana Kacnova; Milda M. Burbuliene; Povilas Vainilavicius

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
360 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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[2‐Alkylthio‐6‐methyl‐4‐oxopyrimidin‐3(4__H__)‐yl]acetonitriles (3‐5) treated with sodium methoxide in methanol followed by ammonium chloride were cyclized to 2‐imino‐7‐methyl‐2,3‐dihydroimidazo[1,2‐a]‐pyrimidin‐5(1__H__)‐ones (6‐8). Under acid or base‐catalyzed hydrolysis they were converted to 7‐methyl‐imidazo[1,2‐a]pyrimidine‐2,5‐[1__H__,3__H__]‐diones (9‐11), whereas in the reaction with butyl‐ or benzylamine the corresponding 7‐methyl‐2‐(substitutedamino)imidazo[1,2‐a]pyrimidin‐5(3__H__)‐ones (13‐18) were produced. The latter were found to exist in two tautomeric forms in CDCl~3~ solution.

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## Abstract Vilsmeier formylation of the 4‐amino‐2‐pyridinones 4a–d leads to the formation of the corresponding 3‐carbaldehydes 5a–d (the diformylated product 8 is isolated as a by‐product). A cyclizing Knoevenagel reaction of 5 with CH‐acidic nitriles 6 in the presence of piperidine gives substitu