A new highly regioselective method for the synthesis of water-soluble 1,3,4-trisubstituted derivatives of tetrahydropyrimidin-2(1H)-one

  1. Andrey V. SmolobochkinORCID Logo,
  2. Almir S. GazizovORCID Logo,
  3. Lola J. Yakhshilikova,
  4. Nikita A. Sidlyaruk,
  5. Airat R. KhamatgalimovORCID Logo,
  6. Alexander R. Burilov and
  7. Michail A. Pudovik

Submitting author affiliation: Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russian Federation

Beilstein Arch. 2022, 202232. https://doi.org/10.3762/bxiv.2022.32.v1

Published 02 May 2022

  • Preprint

Abstract

In this article, we report a regioselective method for the synthesis of new water-soluble 1,3,4-trisubstituted tetrahydropyrimidin-2(1H)-one derivatives containing sodium methanesulfonate fragment in the first position of the heterocycle. The method is based on the reaction of (1-(3,3-diethoxypropyl)ureido)methanesulfonate with aromatic and heterocyclic nucleophiles. The proposed method is distinguished by the possibility of obtaining a wide range of water-soluble substituted tetrahydropyrimidinone derivatives, the absence of the need to use expensive metal complex catalysts, high product yield, and ease of purification.

Keywords: tetrahydropyrimidin-2(1H)-one; electrophilic substitution; C-nucleophiles; acetals

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Smolobochkin, A. V.; Gazizov, A. S.; Yakhshilikova, L. J.; Sidlyaruk, N. A.; Khamatgalimov, A. R.; Burilov, A. R.; Pudovik, M. A. Beilstein Arch. 2022, 202232. doi:10.3762/bxiv.2022.32.v1

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