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Selenium heterocycles XLIV . Syntheses of 8,9‐dihydro‐1,2,3‐thiadiazolo[4,5‐ a ]‐4,7‐dihydroxynaphthalene and 1,2,3‐selenadiazolo[4,5‐ a ]‐4,7‐dimethoxynaphthalene
Author(s) -
Shafiee A.,
Jalilian A. R.,
Rezaei M.
Publication year - 2000
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.5570370551
Subject(s) - chemistry , thionyl chloride , selenium , semicarbazone , medicinal chemistry , chloride , benzoquinone , organic chemistry , stereochemistry
The reaction of thionyl chloride with the semicarbazone 2 gave 4,5‐dihydro‐6,9‐dihydroxynaphtho‐[1,2‐ d ][1,2,3]thiadiazole ( 3 ) instead of 4,5‐dihydro‐6,9‐dimethyoxynaphtho[1,2‐ d ][1,2,3]thiadiazole ( 4 ). Selenium dioxide oxidation of compound 2 gave 4,5‐dihydro‐6,9‐dimethyoxynaphtho[1,2‐ d ][1,2,3]selenadiazole ( 5 ). Oxidation of compound 5 with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone afforded 6,9‐dimethyoxynaphtho[1,2‐ d ][1,2,3]selenadiazole ( 6 ).