Experimental and quantum chemical study of the reactions of 2-methyloxirane with 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo1,2-dihydropyrimidine-4(3H)-one derivatives

The reactions of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-1,2-dihydropyrimidin-4(3 H )-one with 2-methyloxirane in an alkaline medium afforded uracil and 2-[(2-hydroxyprop-1yl)sulfanyl]pyrimidin-4(3 H )-one derivatives. The mechanism proposed for these transformations was studied using the DFT/B3LYP/31...

Full description

Saved in:
Bibliographic Details
Published inRussian chemical bulletin Vol. 64; no. 3; pp. 525 - 533
Main Authors Yablokov, A. S., Steglenko, D. V., Ruchko, E. A., Nawrozkij, M. B., Brunilina, L. L., Novakov, I. A., Minkin, V. I.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.03.2015
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Full Articles
Inorganic Chemistry
Organic Chemistry
one derivatives
B3LYP functional
2-methyloxirane
density functional theory
2-[(2-hydroxyprop-1-yl)sulfanyl]pyrimidin-4
substitution of sulfur
Baker—Nathan effect
Online AccessGet full text

Cover

More Information
Summary:The reactions of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-1,2-dihydropyrimidin-4(3 H )-one with 2-methyloxirane in an alkaline medium afforded uracil and 2-[(2-hydroxyprop-1yl)sulfanyl]pyrimidin-4(3 H )-one derivatives. The mechanism proposed for these transformations was studied using the DFT/B3LYP/311+G** quantum chemical method, and the influence of the Nathan—Baker effect on the chemical nature and composition of the reaction products was shown.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-015-0896-4