The chemistry of 1,2,5‐thiadiazoles, IV. Benzo[1,2‐ c :3,4‐ c ′:5,6‐ c ″] tris [1,2,5] thiadiazole | Zendy

Komin Andrew P. | Zendy; Carmack Marvin | Zendy

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The chemistry of 1,2,5‐thiadiazoles, IV. Benzo[1,2‐ c :3,4‐ c ′:5,6‐ c ″] tris [1,2,5] thiadiazole

Author(s) -

Komin Andrew P.,

Carmack Marvin

Publication year - 1975

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.5570120503

Subject(s) - chemistry , thionyl chloride , diamine , glyoxal , formic acid , nitration , medicinal chemistry , tris , pyrroline , organic chemistry , brucine , thiadiazoles , quinoxaline , chloride , biochemistry , strychnine

Benzo [1,2‐ c :3,4‐ c ′:5,6‐ c ″] tris [1,2,5] thiadiazole (1) was synthesized from benzo [1,2‐ c :3,4‐ c ′] ‐ bis [1,2,5] thiadiazole (11) . Nitration of 11 gave compound 15 , which on direct amination gave nitroamine 17 . Reduction of 17 gave diamine 18 , and cyclization of 18 with thionyl chloride gave 1 . Diamine 18 was also cyclized with selenium oxychloride, glyoxal, 9,10‐phenanthrene‐quinone, and formic acid to give the compounds 4, 5, 19 , and 6 , respectively. A new procedure for the preparation of 2,1,3‐benzothiadiazole (7) from o ‐phenylenediamine was used.

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