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Paper | Regular issue | Vol 63, No. 2, 2004, pp.283-296
Published online, 8th December, 2003
DOI: 10.3987/COM-03-9914
Facile Synthesis of Biologically Active Heterocycles by Indium-induced Reactions of Aromaic Nitro Compounds in Aqueous Ethanol

Bimal K. Banik,* Indrani Banik, Susanta Samajdar, and Mary Wilson

*Department of Molecular Pathology, Box-089, M. D. Anderson Canaer Center, The University of Texas, 515 Holcombe Blvd. , Houston, TX 77030, U.S.A.

Abstract

Indium/ammonium chloride-induced reduction of aromatic nitro compounds to aromatic amines in aqueous ethanol was developed. Useful chemo-selectivity was observed in the reduction reaction. This method was extended to reductive cyclization and rearrangement toward the synthesis of various biologically active heterocycles, including quinoline, oxazines, quinalonones, and phenanthridine in excellent yield. The oxophilicity of indium metal influenced the reaction in aqueous ethanol. Metals like zinc and tin were not effective in promoting this kind of reactions under the present environmentally friendly conditions.