Abstract
A convenient and efficient synthesis of new bis -quinoxaline is described, involving condensation of 1,2-diamines with 9-ethyl-3,6-di(1,2-dioxoethyl)carbazole in the presence of Tonsil clay, a readily available and inexpensive catalyst. The structures of all new products were identified by 1 H-NMR, 13 C-NMR and FT-IR spectral data and microanalysis. KEY WORDS : bis -Quinoxaline, bis -Glyoxal, Green chemistry, 1,2-Diamine, Tonsil clay Bull. Chem. Soc. Ethiop. 2016 , 30(1), 129-136. DOI: http://dx.doi.org/10.4314/bcse.v30i1.12
Highlights
Quinoxaline derivatives have shown a broad spectrum of biological activity including antibacterial, antiviral, anti-inflammatory, kinas inhibitory and anti-cancer activities [1]
We have previously reported the synthesis of bis-glyoxal (1) by the reaction of 3,6-diacetyl9-ethylcarbazole with several oxidizing agents in good yields [19]
Tonsil clay has never been used in quinoxaline synthesis as a heterogeneous catalyst, and can be separated by simple filtration and be recycled
Summary
Quinoxaline derivatives have shown a broad spectrum of biological activity including antibacterial, antiviral, anti-inflammatory, kinas inhibitory and anti-cancer activities [1]. In continuation of our studies on the development of new routes for the synthesis of heterocyclic compounds using aryl glyoxals [13,14,15,16,17,18], we report the synthesis of new bisquinoxaline derivatives from the glyoxal, 9-ethyl-3,6-di(1,2-dioxoethyl)carbazole (1), and 1,2diamines (2) in the presence of the Bentonite clay, Tonsil, as catalyst in solvent free conditions or in ethanol/DMF solvents at reflux (Scheme 1). We have previously reported the synthesis of bis-glyoxal (1) by the reaction of 3,6-diacetyl9-ethylcarbazole with several oxidizing agents in good yields [19].
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