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Alkyl heterocycles in heterocyclic synthesis (II): Novel synthesis of isoquinoline, thiazolopyridine, and thieno[2,3-b]pyridine derivatives

✍ Scribed by Tarek M. Abu Elmaati


Publisher
Journal of Heterocyclic Chemistry
Year
2004
Tongue
English
Weight
57 KB
Volume
41
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

Treating 5‐(4‐phenylcarboxamido)‐3‐cyano‐4‐methylpyridin‐2(1__H__)thione (3) with elemental sulfur yielded thienopyridine 4. Compound 4 reacts with acrylonitrile to give isoquinoline 7. Compound 7 was also, prepared from 3 and methylenemalononitrile. Reaction of 3 with dimethylacetylene dicarboxylate (DMAD) gave the pyridothiazole 9. Also, 3 reacted with N,N‐dimethylchloroacetamide (10) to afford compound 11 which further reacted with the reagents 12, 13 and 14 providing the thieno[2,3‐b]pyridine derivatives 15, 16 and 17 respectively.


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## A simple route to the synthesis of the pharmaceutically important thieno[2,3-d]pyrimidine derivatives and of thieno[2,3-b]pyridine derivatives via the use of 5-amin0-3-phenylthiophene-2,Cdicarbonitrile (2) as a starting material is described.