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Chemistry of thienopyridines. VII. Mechanistic studies on the synthesis of thieno[2,3‐ c ] pyridine by thermolytic cyclization
Author(s) -
Klemm L. H.,
Mccoy D. R.,
Shabtai J.,
Kiang W. K. T.
Publication year - 1969
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.5570060607
Subject(s) - chemistry , ethanethiol , pyridine , sulfide , yield (engineering) , hydrogen sulfide , thermal decomposition , medicinal chemistry , organic chemistry , decomposition , sulfur , materials science , metallurgy
A study was made of the formation of thieno[2,3‐ c ]pyridine (1) from hydrogen sulfide and 4‐vinylpyridine in a flow system at 630°. 2‐(4‐Pyridyl)ethanethiol and bis‐2‐(4‐pyridyl)ethyl sulfide were found to be likely intermediates. Based on these studies, there was devised a two‐step practical preparative method for I (optimum overall yield 58%) which consists of preliminary conversion of 4‐vinylpyridine to benzyl 2‐(4‐pyridyl)ethyl sulfide and subsequent thermolysis (at 605°) of this substance.