Specific features of amidoalkylation of 6-hydroxy-5-isopropyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

During the synthesis of new structural analogs of isothiobarbamine, the amidoalkylation of 6-hydroxy-5-isopropyl-2-thioxo-2,3-dihydropyrimidin-4(1 H )-one was found to give a mixture of mono-, di-, and trisubstituted products. Possible explanations for low regioselectivity of the reaction are given.

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Bibliographic Details
Published inRussian chemical bulletin Vol. 69; no. 12; pp. 2363 - 2369
Main Authors Novakov, I. A., Sheikin, D. S., Chapurkin, V. V., Nawrozkij, M. B., Kirillov, I. A., Ruchko, E. A.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.12.2020
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Full Articles
Inorganic Chemistry
Organic Chemistry
regioselectivity
isothiobarbamine
amido-alkylation
6-hydroxy-5-isopropyl-2-thioxo-2,3-dihydropyrimidin-4
one
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Summary:During the synthesis of new structural analogs of isothiobarbamine, the amidoalkylation of 6-hydroxy-5-isopropyl-2-thioxo-2,3-dihydropyrimidin-4(1 H )-one was found to give a mixture of mono-, di-, and trisubstituted products. Possible explanations for low regioselectivity of the reaction are given.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-020-3029-7