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One-pot sequential coupling reactions as a new practical protocol for the synthesis of unsymmetrical 2,3-diethynyl quinoxalines and 4-ethynyl-substituted pyrrolo[1,2-a]quinoxalines

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Abstract

One palladium-catalyzed sequential coupling reactions were successfully used as a new protocol for the synthesis of unsymmetrical 2,3-diethynyl quinoxalines and 4-ethynyl-substituted pyrrolo[1,2-a]quinoxalines. The one-pot two coupling reactions of 2,3-dichloroquinoxaline, with two different terminal alkynes, under controlled conditions produced selectively unsymmetrical 2,3-diethynyl quinoxalines with high yields. When one of the two terminal alkynes was 3-propyne-1-ol, in the presence of secondary amines, cyclization occurred and 4-ethynyl-substituted pyrrolo[1,2-a]quinoxalines were successfully formed. All synthesized compounds were tested against the two bacterial strains including Micrococcus luteus and Pseudomonas aeruginosa.

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Acknowledgements

The authors wish to express their thanks to the Research Council of the Shahrood University of Technology for the financial support of this research work.

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  1. Faculty of Chemistry, Shahrood University of Technology, Shahrood, 36199-95161, Iran

    Ali Keivanloo, Saeed Lashkari, Mohammad Bakherad, Mahsa Fakharian & Sima Abbaspour

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  1. Ali Keivanloo
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  2. Saeed Lashkari
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Keivanloo, A., Lashkari, S., Bakherad, M. et al. One-pot sequential coupling reactions as a new practical protocol for the synthesis of unsymmetrical 2,3-diethynyl quinoxalines and 4-ethynyl-substituted pyrrolo[1,2-a]quinoxalines. Mol Divers 25, 981–993 (2021). https://doi.org/10.1007/s11030-020-10083-5

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