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Synthesis and Photolysis of Azido-benzothiophens, -benzothiazoles, -benzimidazoles, and -indazoles: Novel 6,7-diamino-benzothiazoles, -benzimidazoles, and -indazoles and 6-Diethylamino-8H-thiazoloazepines

DOI: 10.1039/P19800002362

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2362 - 2370 (1980)

Update date:2022-08-04

Topics:

Authors:

Gallagher, Peter T.Gallagher, Peter T.

Iddon, BrianIddon, Brian

Suschitzky, HansSuschitzky, Hans

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Article abstract of DOI:10.1039/P19800002362

Irradiation of the 6-azidobenzothiazoles (4)-(9) (see Scheme) in the presence of an excess of a secondary amine gave either the corresponding 6,7-diaminobenzothiazole (14)-(20), a 6-amino-8H-thiazolo<5,4-c>azepine (21)-(24), a mixture of both, or intractable material .Irradiation of 7-azido-3-methylbenzothiophen in an excess of diethylamine gave 7-amino-3-methylbenzothiophen and a trace of 3,3'-dimethyl-7,7'-azobenzothiophen. 6-Azidoindazole gave 7-amino-6-diethylaminoindazole (32) and 5(6)-azidobenzimidazole gave a mixture of 4(7)-amino- 5(6)-diethylaminobenzimidazole (33) and 5(6)-amino-4(7)-diethylaminobenzimidazole (34).Photolysis of either 6-azidobenzothiazole or its 2-methyl derivative in a methoxide-methanol-dioxan mixture gave the corresponding 6-methoxy-8H-thiazolo<5,4-c>azepine, (30) or (31), respectively.

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Product name:N6,N6-Diethyl-2-phenylsulfanyl-benzothiazole-6,7-diamine

Cas No:76007-06-2

76007-06-2

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