Tautomerism of diazepines fused with pyrimidine rings [Review]

摘要

The tautomerism of 1,4-diazepines fused with pyrimidine rings was studied by means of nmr spectroscopy, X-ray analysis and quantum chemical calculations. It was found that in the case of 6,8-diphenylpyrimido[4,5-b][1,4]diazepin-4-ols (7a - e) the enamine form is more stable than the diimine form. This result is rationalized with the electron-withdrawing effect of the 4-hydroxypyrimidine ring and with the formation of intermolecular hydrogen bonds. In contrast to 7a - e, the 6,8-diaryl-2,3,4,7-tetrahydro-1,3-dimethyl-1H-pyrimido[4,5-b][1,4]diazepin e-2,4-diones (9a, c, f) exist in the diimine form. [References: 22]