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Chemistry of thienopyridines. XV. Syntheses of thieno [3,4‐ b ] ‐ and thieno[3,4‐ c ] pyridines
Author(s) -
Klemm L. H.,
Johnson W. O.,
White D. V.
Publication year - 1972
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.5570090414
Subject(s) - chemistry , pyridine , condensation , sulfoxide , medicinal chemistry , dehydration , sodium , sodium sulfide , catalysis , sulfide , organic chemistry , biochemistry , thermodynamics , physics
Thieno [3,4‐ b ] pyridine (5) was synthesized by means of the successive steps of (a) photochlorination of 2,3‐dimethylpyridine to the bis(chloromethyl) compound, (b) condensation with sodium sulfide, (c) oxidation to the sulfoxide, and (d) catalytic dehydration by means of alumina. Thieno[3,4‐ c ]pyridine (6) was obtained in an analogous manner. Spectral properties indicate that 5 and 6 have aromatic character.