The Effect of the Azole Ring on the Conformational Mobility of the Dihydropyrimidine Ring in 4,7-Dihydroazolo[1,5-a]Pyrimidines as Judged from MNDO Calculations

Authors

O. V. Shishkin, Kharkov State UniversityFollow
S. M. Desenko, Kharkov State University
V. D. Orlov, Kharkov State University
Sergey Lindeman, Marquette UniversityFollow
Yu T. Struchkov, Russian Academy of SciencesFollow
A. S. Polyakova, Kharkov Polytechnical InstituteFollow
E. I. Mikhedkina, Kharkov Polytechnical University

Document Type

Article

Language

eng

Publication Date

8-1994

Publisher

Springer

Source Publication

Russian Chemical Bulletin

Source ISSN

1066-5285

Abstract

The equilibrium geometries of 4,7-dihydropyrazolo[1,5-a]pyrimidine, 4,7-dihydrotetrazolo [1,5-a]pyrimidine, 4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine, and 1,4-di-hydropyrimido [1,2-a]imidazole were calculated by the semiempirical quantum-chemical MNDO method. The dihydropyrimidine ring exhibits high conformational mobility in all of these compounds. The change in the energy occurring in the transition of the molecule to the boat conformation with an angle between the planar fragments of ±20° does not exceed 1 kcal mol⁻¹. The mobility of the dihydro ring increases as interactions between the π-systems of the azole ring and the C=C double bond separated by an imino group and a methylene bridge decrease.

Comments

Russian Chemical Bulletin, Vol. 43, No. 8 (August 1994): 1343-1345. DOI.

Sergey Lindeman was affiliated with Russian Academy of Sciences at the time of publication.

Recommended Citation

Shishkin, O. V.; Desenko, S. M.; Orlov, V. D.; Lindeman, Sergey; Struchkov, Yu T.; Polyakova, A. S.; and Mikhedkina, E. I., "The Effect of the Azole Ring on the Conformational Mobility of the Dihydropyrimidine Ring in 4,7-Dihydroazolo[1,5-a]Pyrimidines as Judged from MNDO Calculations" (1994). Chemistry Faculty Research and Publications. 670.
https://epublications.marquette.edu/chem_fac/670