Nucleophilic substitution at the C(4)atom in series of functionally 4-substituted hexahydropyrimidine-2-thiones. Synthesis of 4-alkylthiohexahydropyrimidine-2-thiones

✍ Scribed by L. A. Ignatova; A. D. Shutalev; M. T. Pagaev; B. V. Unkovskii

• Publisher: Springer US
• Year: 1988
• Tongue: English
• Weight: 630 KB
• Volume: 24
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00473332

✦ Synopsis

Nucleophilic substitution at the C(~) atom in 4-hydroxy(alkoxy)hexahydropyrimidine-2-thiones under the influence of alkanethiols in acidic, neutral, and basic media, as a result of which 4-alkylthiohexahydropyrimidine-2-thiones are formed, was studied. Hydrolysis and alcoholysis of the latter lead to the corresponding 4-hydroxy-or 4-alkoxyhexahydropyrimidine-2-thiones. The three-dimensional structures of the 4-alkylthiopyrimidines obtained were established by PMR spectroscopy, and it was shown that the stereoisomers with an axially oriented alkylthio group are thermodynamically more stable.