This article is cited in 44 papers

Nucleophilic attack on the unsubstituted carbon atom of azines and nitroarenes as an efficient methodology for constructing heterocyclic systems

O. N. Chupakhin, D. G. Beresnev

I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, Ekaterinburg

Abstract: Data on new methods for the synthesis of fused azines by nucleophilic attack on the unsubstituted carbon atom of azines and nitroarenes are generalised. The review surveys tandem reactions of azines with binucleophiles comprising nucleophilic addition A_N – A_N nucleophilic addition – substitution A_N – S^ipso_N, and nucleophilic substitutions S^H_N – S^ipso_N and S^H_N-S^H_N. Intramolecular S^H_N reactions of azines and nitroarenes and other methods for the synthesis of fused heterocycles based on S^H_N nucleophilic substitution are also discussed. The bibliography includes 69 references.

Received: 24.06.2002

DOI: 10.1070/RC2002v071n09ABEH000747

 English version: Russian Chemical Reviews, 2002, 71:9, 707–720

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