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Vanillic aldehydes for the one-pot synthesis of novel 2-oxo-1,2,3,4-tetrahydropyrimidines

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Abstract

A small library of novel 2-oxo-1,2,3,4-tetrahydropyrimidines was synthesized via a one-pot multicomponent Biginelli reaction. Copper complex \((\hbox {PhNH}_{3})_{2}\hbox {CuCl}_{4,}\) which was used for the first time as a homogeneous and heterogeneous catalyst, makes this a facile and efficient reaction at room temperature. All the obtained products fall out of the solution in pure form and are easily isolated via filtration in good-to-excellent yields. The molecular structure of one of the products, ethyl 6-methyl-2-oxo-4-(4\(^\prime \)-isopropoxy-3\(^\prime \)-methoxyphenyl) - 1,2,3,4 - tetrahydropyrimidine-5- carboxylate, has been determined by X-ray crystallography. All non-hydrogen atoms in the heterocyclic, six-membered ring are determined to be approximately coplanar.

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Acknowledgments

The authors are grateful to the Ministry of Education, Science and Technological Development of the Republic of Serbia for financial support (Grants 172011 and 172034).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Kragujevac, Radoja Domanovića 12, P.O. Box 60, Kragujevac, 34 000, Serbia

    Jovana Muškinja, Nenad Janković, Zoran Ratković & Zorica Bugarčić

  2. Laboratory of Theoretical Physics and Condensed Matter Physics, Faculty of Science, Vinča Institute of Nuclear Science, University of Belgrade, P.O. Box 522, Belgrade, 11001, Serbia

    Goran Bogdanović

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  1. Jovana Muškinja
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  2. Nenad Janković
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Correspondence to Nenad Janković.

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Muškinja, J., Janković, N., Ratković, Z. et al. Vanillic aldehydes for the one-pot synthesis of novel 2-oxo-1,2,3,4-tetrahydropyrimidines. Mol Divers 20, 591–604 (2016). https://doi.org/10.1007/s11030-016-9658-y

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