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.
Graphical Abstract
Letters in Organic Chemistry
Title:Highly Regioselective Route to Substituted Imidazo[1,2-a]quinoxalines
Volume: 15 Issue: 5
Author(s): Balendu Singh, Anand Acharya and Hiriyakkanavar Ila*
Affiliation:
- New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bengaluru,India
Keywords: Imidazo[1, 2-a]quinoxalines, aminoacetaldehyde dimethylacetal, chloroquinoxalines, (methylsulfonyl)imidazo[1, 2- a]quinoxalines, anti-allergic, unsymmetrically.
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.
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Cite this article as:
Singh Balendu , Acharya Anand and Ila Hiriyakkanavar *, Highly Regioselective Route to Substituted Imidazo[1,2-a]quinoxalines, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178615666180108154309
DOI https://dx.doi.org/10.2174/1570178615666180108154309 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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