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Alkyl heterocycles in heterocyclic synthesis (II): Novel synthesis of isoquinoline, thiazolopyridine, and thieno[2,3‐ b ]pyridine derivatives
Author(s) -
Abu Elmaati Tarek M.
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410614
Subject(s) - chemistry , isoquinoline , acrylonitrile , thienopyridine , pyridine , reagent , medicinal chemistry , alkyl , sulfur , quinoline , organic chemistry , polymer , biochemistry , aspirin , copolymer , clopidogrel
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.