Synthesis of Bisfurazanobenzo-2,1,3-thiadiazole and Related Compounds

概要

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Nitration of 4,7-dibromobenzo-2,1,3-thiadiazole (I) with fuming nitric acid afforded 4,7-dibromo-5,6-dinitrobenzo-2,1,3-thiadiazole (II) and, unexpectedly, the tribromo derivative : C_6Br_3N_3O_2S (III). Compound II was readily converted by treatment with sodium azide into bisfuroxanobenzo-2,1,3-thiadiazole (IV), which was reduced with triethylphosphite to give bisfurazanobenzo-2,1,3-thiadiazole (VII). Compound VII was also synthesized starting from 4-bromo-6,7-(2', 1', 3'-oxadiazole) benzo-2,1,3-thiadiazole (VIII). Reduction of VII with sodium hydrosulfite gave 4,5-diamino-6,7-(2', 1', 3'-oxadiazole)-benzo-2,1,3-thiadiazole (XI), which was cyclized to 4,5-(2', 1', 3'-oxadiazole) benzo [1,2-c : 3,4-c'] bis [1,2,5] thiadiazole (XII) by treatment with N-sulfinylaniline. The transformation of XII to benzo [1,2-c : 3,4-c' : 5,6-c"] tris [1,2,5] thiadiazole (XIV), via 4,5-diaminobenzo-[1,2-c : 3,4-c'] bis [1,2,5] thiadiazole (XIII), is also described.
社団法人日本薬学会の論文
1980-06-25