Efficient formation of σ H-adducts as a key step in the synthesis of acridines via Lewis acid-promoted transformations of the nitro group

M Bobin, A Kwast, Z Wróbel

Index: Bobin, Mariusz; Kwast, Andrzej; Wrobel, Zbigniew Tetrahedron, 2007 , vol. 63, # 45 p. 11048 - 11054

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Citation Number: 15

Abstract

A step-by-step methodology was applied in the Lewis acid-promoted synthesis of fused heterocyclic systems from carbanions and nitroarenes. Efficient formation of σH-adducts of substituted nitrobenzenes and phenylacetonitrile derivatives followed by reductive transformation of the nitro group with silylating or acylating agents leads to 9- cyanoacridines. The method was found to be superior to the earlier one-pot approach, ...