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Highly Regioselective Route to Substituted Imidazo[1,2-a]quinoxalines

[ Vol. 15 , Issue. 5 ]

Author(s):

Balendu Singh, Anand Acharya and Hiriyakkanavar Ila*   Pages 441 - 446 ( 6 )

Abstract:


A new synthesis of unsymmetrically substituted imidazo[1,2-a]quinoxalines via regioselective displacement of 3-chloro group in 2-(methylthio)-3-chloroquinoxalines by aminoacetaldehyde dimethylacetal and subsequent-acid mediated intramolecular cyclization of the resulting adducts is reported in this study. The utility of the 3-(methylthio) group in these imidazoquinoxalines is also demonstrated by conversion of one of the 2-(methylthio)quinoxalines to 2-(methylsulfonyl) derivative and its subsequent displacement by hydroxy-, phenoxy- and n-butylamino groups, thus affording various 2-substituted imidazo[1,2-a]quinoxalines.

Keywords:

Imidazo[1, 2-a]quinoxalines, aminoacetaldehyde dimethylacetal, chloroquinoxalines, (methylsulfonyl)imidazo[1, 2- a]quinoxalines, anti-allergic, unsymmetrically.

Affiliation:

Department of Chemistry, Indian Institute of Technology, Kanpur, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bengaluru, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bengaluru

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