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Selenium heterocycles. XLI . Syntheses of substituted thiazolo, selenazolo, 1,2,3‐thiadiazolo and 1,2,3‐selenadiazoloquinolines
Author(s) -
Shafiee A.,
Rezayazdi M.
Publication year - 1995
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.5570320128
Subject(s) - chemistry , quinoline , thionyl chloride , selenium , medicinal chemistry , thermal decomposition , chloride , organic chemistry
The reaction of thionyl chloride with the semicarbazone 2 gave 4,5‐dihydro[1,2,3]thiadiazolo[4,5‐ f ]quinoline. Selenium dioxide oxidaion of compound 2 gave 4,5‐dihydro[1,2,3]selenadiazolo[4,5‐ f ]quinoline ( 4 ) and the aromatic analog 5 . Thermolysis of compound 5 yielded [1,4]diselenino[2,3‐ f :5,6‐ f ′]diquinoline ( 6 ). Reaction of selenourea with α‐bromoketone 7 gave 2‐amino‐4,5‐dihydroselenazolo[4,5‐ f ]quinoline ( 8 ). Compounds 9 and 10 were prepared from the reaction of selenobenzamide and thiobenzamide with compound 7 .