Title

Conformational Analysis of 5,6-dihydropyrimidine and Its Derivatives

Document Type

Article

Language

eng

Publication Date

3-1995

Publisher

Springer

Source Publication

Russian Chemical Bulletin

Source ISSN

1066-5285

Abstract

The equilibrium geometry and inversion barriers of 5,6-dihydropyrimidine, 6,7-dihydroazolopyrimidines with node nitrogen atoms and their alkyl (Me, Et, Pri, But) and phenyl derivatives were calculated using a molecular mechanics approach. Annelation with azole cycles and the introduction of substituents have a slight effect on the equilibrium conformation of the dihydrocycle (distorted sofa). Alkyl substutuents at saturated carbons have an essentially equatorial orientation in 5,6-dihydropyridimine derivatives and are axial in the annelated analogs. On the other hand, the equatorial conformers are more stable in phenyl derivatives of dihydroazolopyrimidines. Factors determining the relative stability of conformers were analyzed.

Comments

Russian Chemical Bulletin, Vol. 44, No. 3 (March 1995): 470-474. DOI.

Sergey Lindeman was affiliated with A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation at time of publication.

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