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Eco-friendly and regiospecific intramolecular cyclization reactions of cyano and carbonyl groups in N,N-disubstituted cyanamide

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Abstract

Eco-friendly, low-cost and high-yielding synthetic route toward imidazoles and oxazoles has been developed. 1-(4,6-Dimethylpyrimidin-2-yl)-2-(alkylamino)-1,5-dihydro-4H-imidazol-4-one 3a–c have been synthesized via regiospecific reaction of ethyl 2-(N-(4,6-dimethylpyrimidin-2-yl)cyanamide)acetate 1 with primary aliphatic amines in water as green solvent. While, the reaction between 4,6-dimethylpyrimidin-2-yl(2-oxo-2-phenylethyl)cyanamide 2 and primary aliphatic amines using water and/or iso-propanol as green solvents afforded 3-(4,6-dimethylpyrimidin-2-yl)-5-phenyl-1,3-oxazole-2(3H)-imine 6 and 1-(4,6-dimethylpyrimidin-2-yl)-N-alkyl-4-phenyl-1H-imidazol-2-amine 7a–d, respectively.

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Acknowledgements

The authors extend their appreciation to Taif University for funding the current work under Taif University Researchers Supporting Project number (TURSP—2020/111), Taif University, Taif, Saudi Arabia.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Sohag University, Sohag, 82524, Egypt

    Amr H. Moustafa, Walaa W. Ahmed, Ahmed Khodairy & Amer A. Amer

  2. Department of Biology, College of Science, Taif University, P.O. Box 11099, Taif, 21944, Saudi Arabia

    Mohamed F. Awad

  3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Sohag University, Sohag, 82524, Egypt

    Moustafa O. Aboelez

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  1. Amr H. Moustafa
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Moustafa, A.H., Ahmed, W.W., Awad, M.F. et al. Eco-friendly and regiospecific intramolecular cyclization reactions of cyano and carbonyl groups in N,N-disubstituted cyanamide. Mol Divers 26, 2813–2823 (2022). https://doi.org/10.1007/s11030-022-10401-z

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