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

Andrey V. Smolobochkin; Almir S. Gazizov; Lola J. Yakhshilikova; Nikita A. Sidlyaruk; Airat R. Khamatgalimov; Alexander R. Burilov; Michail A. Pudovik

doi:10.3762/bxiv.2022.32.v1

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

Andrey V. Smolobochkin ,
Almir S. Gazizov ,
Lola J. Yakhshilikova ,
Nikita A. Sidlyaruk ,
Airat R. Khamatgalimov ,
Alexander R. Burilov and
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

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Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

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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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

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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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)