The computational study of substituent influence on the anomeric effect, aromatization and hydride removal in 1, 4 DHPs

Anomeric effect was introduced by stereoelectronical effect on carbohydrate chemistry almost 60 years ago. It caused preference of electronegative substituent in axial than equatorial position of pyranoid ring systems. Now anomeric effect is known as a basic issue in chemistry and has significant role in the field of organic transformations 1, 2. For the first time the role of anomeric effect in oxidative aromatization of some heterocyclic molecules was investigated by our research groups and named "anomeric base oxidation (ABO)". Oxidation is happening by transfer of heteroatom lone pair electrons through resonance, then electrons interact with anti-bonding orbital of C-H bond and make hydride removal from the intermediate 3, 4. In continuation of this research on ABO, was evaluated the substituent influence on cooperative vinylogous anomeric effect and aromatization in 1,4-DHPs (1,4-dihydropyridines). The characterization and energy of substituent effect on some of the 1,4-DHP derivatives were computed and found that the properties of substituent can play important role in anomeric effect and aromatization of these compounds.

کلیدواژه ها:

Computational study ، Anomeric effect ، Anomeric base oxidation ، 1 ، 4 DHPs