Journal of the Chemical Society. Perkin transactions I p. 2387 - 2391 (1980)
Update date:2022-08-05
Topics:
Hawkins, David
Lindley, John M.
McRobbie, Ian M.
Meth-Cohn, Otto
2-(2-Nitrophenyl)benzothiazole, produced by deoxygenation of the corresponding nitro-compound or by thermolysis or photolysis of the related azide, gives indazolo<3,2-b>benzothiazole by attack on the benzothiazole nitrogen.Similar attack of the nitrene in 2-(2-nitrophenyl)benzimidazoles gives benzimidazoindazoles in good yield.However, with an appropriate 1-substituent in the benzimidazole (e.g.Me or CHMe2) the nitrene in its triplet state (generated by acetophenone-sensitised photolysis or by thermolysis of the azide bearing a 4-dimethylamino-group) preferentially attacks this substituent giving benzimidazoquinazolines.
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