Bioorganic & Medicinal Chemistry 2012-03-01

AlCl3 induced (hetero)arylation of 2,3-dichloroquinoxaline: a one-pot synthesis of mono/disubstituted quinoxalines as potential antitubercular agents.

K Shiva Kumar, D Rambabu, Sandhya Sandra, Ravikumar Kapavarapu, G Rama Krishna, M V Basaveswara Rao, Kiranam Chatti, C Malla Reddy, Parimal Misra, Manojit Pal

Index: Bioorg. Med. Chem. 20(5) , 1711-22, (2012)

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Abstract

A direct and single-step method has been developed for the synthesis of mono and 2,3-disubstituted quinoxalines by using a AlCl(3) induced (hetero)arylation of 2,3-dichloroquinoxaline. Both symmetrical and unsymmetrical 2,3-disubstituted quinoxalines can be prepared conveniently by using this method under appropriate reaction conditions. The reaction proceeds via C-C bond formation and can be utilized for the preparation of a variety of quinoxaline derivatives from readily available starting materials and reagents. The molecular structure of a representative compound was confirmed by single crystal X-ray diffraction study. Some of the compounds synthesized were tested for chorismate mutase inhibitory properties in vitro and one compound showed promising activity representing one of the few examples of chorismate mutase inhibition by a heteroarene based small molecule.Copyright © 2012 Elsevier Ltd. All rights reserved.