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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

✍ Scribed by A. Shafiee; A. R. Jalilian; M. Rezaei

Publisher: Journal of Heterocyclic Chemistry
Year: 2000
Tongue: English
Weight: 188 KB
Volume: 37
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570370551

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✦ Synopsis

Abstract

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).

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