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Synthesis of tricyclic and tetracyclic thieno[3,2‐ f ]‐1,4‐thiazepines
Author(s) -
Tanaka Hiroshi,
Nakao Tohru
Publication year - 1997
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.5570340332
Subject(s) - chemistry , tricyclic , hydrazine (antidepressant) , hydrate , stereochemistry , medicinal chemistry , organic chemistry , chromatography
Treatment of 5‐methylthio‐2,3‐dihydrothieno[3,2‐ f ]‐1,4‐thiazepine ( 9 ) with acylhydrazines gave 5,6‐dihydrothieno[3,2‐ f ]‐1,2,4‐triazolo[4,3‐ d ][1,4]thiazepines 10, 11 , and that of 9 with ethyl anthranilate gave 5,6‐dihydrothieno[3′,2′:6,7][1,4]thiazepino[5,4‐ b ]quinazolin‐8‐one ( 14 ). Reaction of 9 with hydrazine hydrate or 4‐chlorophenylhydrazine afforded 5‐hydrazino compounds 12, 15 , which were subsequently cyclized to ethyl 5,6‐dihydrothieno[3,2‐ f ]‐1,2,4‐triazolo[4,3‐ d ][1,4]thiazepine‐3‐carboxylate ( 13 ), 2‐(4‐chlorophenyl)‐5,6‐dihydrothieno[3,2‐ f ]‐1,2,4‐triazolo[4,3‐ d ][1,4]thiazepin‐3(2 H )‐one ( 16 ) and 2‐(4‐chlorophenyl)‐6,7‐dihydro‐2 H ‐thieno[3,2‐ f ][1,2,4]triazino[4,3‐ d ][1,4]thiazepine‐3,4‐dione ( 17 ). New thieno‐anellated heterocycles were prepared with the aim of studying their affinity for the benzodiazepine receptors.