Issue 0, 1980
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Competitive cyclisations of singlet and triplet nitrenes. Part 9. 2-(2-Nitrenophenyl)-benzothiazoles and -benzimidazoles

David Hawkins,   John M. Lindley,   Ian M. McRobbie  and  Otto Meth-Cohn  

Abstract

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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Article information

DOI
https://doi.org/10.1039/P19800002387
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1980, 2387-2391

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Competitive cyclisations of singlet and triplet nitrenes. Part 9. 2-(2-Nitrenophenyl)-benzothiazoles and -benzimidazoles

D. Hawkins, J. M. Lindley, I. M. McRobbie and O. Meth-Cohn, J. Chem. Soc., Perkin Trans. 1, 1980, 2387 DOI: 10.1039/P19800002387

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