Chemistry of thienopyridines. VII. Mechanistic studies on the synthesis of thieno[2,3‐ c ] pyridine by thermolytic cyclization | Zendy

Klemm L. H. | Zendy; Mccoy D. R. | Zendy; Shabtai J. | Zendy; Kiang W. K. T. | Zendy

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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.

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