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N-methylpyrrolidine as an effective organocatalyst for the regioselective synthesis of 3-hydroxy-3,5/6-di-aryl-1H-imidazo[1,2-a]imidazol-2(3H)-ones

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Abstract

N-Methylpyrrolidine catalyzed, concise and attractive synthesis of a new class of 3-hydroxy-3,5/6-di-aryl-1H-imidazo[1,2-a]imidazol-2(3H)-ones was attained with impressive yields, in the presence of EtOH as a solvent, by means of a convenient and elegant condensation reaction between different aryl glyoxal monohydrates and guanidine hydrochloride under reflux conditions. Some specific merits of the current procedure, including encompasses low operating cost, availability of the starting substrates, reasonable reaction times, high reaction yield, operational simplicity, cleaner reaction profile, no harmful by-products, and the isolated product is in pure form. Structures of all the freshly synthesized products have been deduced by their FT-IR, 1H-NMR, 13C-NMR, Mass spectrometry data and microanalysis.

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Acknowledgements

The authors are appreciatively thankful for all supports of the Urmia University.

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  1. Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran

    Bayram Parsa Habashi & Ahmad Poursattar Marjani

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  1. Bayram Parsa Habashi
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  2. Ahmad Poursattar Marjani
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Correspondence to Ahmad Poursattar Marjani.

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Parsa Habashi, B., Poursattar Marjani, A. N-methylpyrrolidine as an effective organocatalyst for the regioselective synthesis of 3-hydroxy-3,5/6-di-aryl-1H-imidazo[1,2-a]imidazol-2(3H)-ones. Res Chem Intermed 48, 2325–2336 (2022). https://doi.org/10.1007/s11164-022-04717-6

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