Issue 9, 1992
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Mannich/Friedel–Crafts preparations of 1-(arylmethyl)benzotriazoles and synthetic transformations of their lithio derivatives

Alan R. Katritzky,   Mikhail F. Gordeev,   John V. Greenhill  and  Peter J. Steel  

Abstract

The synthesis of 1-(arylmethyl)benzotriazoles by Mannich type reactions of benzene, toluene, p-xylene and chlorobenzene with 1-chloromethylbenzotriazole in the presence of aluminium halides is reported. Alkylation, of their lithio derivatives followed by the cleavage of benzotriazole from the resulting 1-(α-arylalkyl)benzotriazoles upon reduction with LiAlH4–AlCl3 or elimination by AcOH are shown to be useful procedures for the preparation of substituted arenes. An oxidative coupling of lithiated 1-(arylmethyl)benzotriazoles gave 1,2-diaryl-1,2-di(benzotriazol-1-yl)ethanes. Novel heterocyclic ring fissions of the lithio derivatives of 1-(arylmethyl)benzotriazoles afforded 1,2,4-benzotriazine and 1,2-bis(N-methylanilino)ethene derivatives.

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Article information

DOI
https://doi.org/10.1039/P19920001111
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1992, 1111-1117

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Mannich/Friedel–Crafts preparations of 1-(arylmethyl)benzotriazoles and synthetic transformations of their lithio derivatives

A. R. Katritzky, M. F. Gordeev, J. V. Greenhill and P. J. Steel, J. Chem. Soc., Perkin Trans. 1, 1992, 1111 DOI: 10.1039/P19920001111

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