Moloney G P, Craik D J, Iskander M N
School of Pharmaceutical Chemistry, Victorian College of Pharmacy Ltd., Parkville, Australia.
J Pharm Sci. 1992 Jul;81(7):692-7. doi: 10.1002/jps.2600810721.
A series of 3,4-dihydro-1,3-benzoxazine and 3,4-dihydro-1,3-pyridooxazine derivatives was synthesized, and the hydrolysis of the derivatives was studied with proton nuclear magnetic resonance spectroscopy. The oxazine derivatives underwent various degrees of hydrolysis when H2O was added to dimethyl sulfoxide solutions of the compounds. The rates and extents of decomposition of the oxazine ring systems depended on the electronic effects of substituents within the molecules. Examination of the proton nuclear magnetic resonance spectra that were generated during decomposition of the oxazines and trends in stability of the oxazine derivatives suggest the formation of an intermediate in the hydrolysis mechanism.
合成了一系列3,4-二氢-1,3-苯并恶嗪和3,4-二氢-1,3-吡啶并恶嗪衍生物，并采用质子核磁共振光谱法研究了这些衍生物的水解情况。当向这些化合物的二甲基亚砜溶液中加入水时，恶嗪衍生物会发生不同程度的水解。恶嗪环体系的分解速率和程度取决于分子内取代基的电子效应。对恶嗪分解过程中产生的质子核磁共振光谱以及恶嗪衍生物稳定性趋势的研究表明，水解机理中会形成一种中间体。
