Cobalt perchlorate hexahydrate catalyzed one-pot synthesis of dihydropyrimidin-ones/-thiones through sonochemistry and its mechanistic study using density functional theory calculations |
| |
Authors: | Ramesh Ambatwar Sumit Kumar Dhairiya Agarwal Lokesh Chandrakar Gopal L. Khatik |
| |
Affiliation: | Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research-Raebareli, Lucknow, Uttar Pradesh, India |
| |
Abstract: | A cobalt(II) perchlorate hexahydrate coordinated synthesis of dihydropyrimidin-ones and -thiones through sonochemistry is developed. Herein, the reaction was demonstrated as a simple, efficient, and one-pot method for synthesizing a series of interesting 3,4-dihydropyrimidin-2(1H)-ones. Further, the reaction mechanism was investigated using mass spectrometry and density functional theory calculations suggesting that a Lewis acid character of cobalt(II) perchlorate hexahydrate plays a crucial role in coordinating carbonyl functionalities and stabilizing the polar intermediates like imine–enamine which further led to cyclized dihydropyrimidin-ones and -thiones. This methodology was further explored to synthesize a gram-scale synthesis of monastrol drug, a kinase inhibitor. |
| |
Keywords: | |
|
|