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Paper | Regular issue | Vol 45, No. 12, 1997, pp.2413-2423
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8016
A Facile General Synthesis of 9-Position Functionalised Heteroniumanthracene Salts

Alan R. Katritzky,* Sergey N. Denisenko, and Peter Czerney

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


Heteroniumanthracenes react selectively as the cations (1a) or as the corresponding carbinol bases (9a,c) with benzotriazole to give the corresponding 9H-(benzotriazol-1-yl)heterocycles (10a-c). As novel heterocyclic anion precursors, (10a-c) undergo smooth lithiations at the positions α to the benzotriazol-1-yl function, corresponding to the 9-position of the heterocycles (1a) and (9b,c). Subsequent trapping of the benzotriazolyl stabilised carbanions (11a-c) with various long chain alkyl halides forms intermediates of type (12b) which are converted by treatment with mineral acid, into the corresponding 9-functionalised heteroniumanthracene salts (13-16) (or their free bases (17-19)) in good to excellent yields.