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
Ov. Shishkin et al., 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, Russian chemical bulletin, 43(8), 1994, pp. 1343-1345
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-dihydropyrimido[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 degrees does not exceed 1 kcal mol(-1). The mobility of the dih
ydro ring increases as interactions between the pi-systems of the azol
e ring and the C=C double bond separated by an imino group and a methy
lene bridge decrease.