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Pure Appl. Chem., 2004, Vol. 76, No. 9, pp. 1621-1631

SNH methodology and new approaches to condensed heterocyclic systems

V. N. Charushin and O. N. Chupakhin

Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya st. 20, 620219, Ekaterinburg, Russia

Abstract: The review surveys the reactions of electron-deficient azaaromatic compounds with mono- and bifunctional nucleophilies in which a nucleophilic attack at the unsubstituted CH carbon of an aromatic ring is one of the key steps. Use of the SNH methodology for the synthesis of fused heterocyclic systems by means of nucleophilic addition –addition AN–AN, addition –substitution of hydrogen AN–SNH, tandem substitution of hydrogen SNH–SNH, and other strategies will be discussed. Intramolecular SNH reactions will also be considered as effective synthetic tools to obtain condensed heterocyclic systems.