An ab initio study and the corresponded instructing improvement of the multicomponent reaction consisted of acetone, aniline and 4-hydrocoumarine

Publication date: Available online 31 October 2018Source: Computational and Theoretical ChemistryAuthor(s): Guoxun Zhu, Dongting Huang, Wenyan Cao, Huacan Song, Ao YouAbstractMulti-component reaction (MCR) is a powerful, versatile and step-economical approach in organic synthesis due to reducing reaction steps and simplifying operation. An ab initio study was carried out on the MCR of acetone, aniline and 4-hydro-coumarine, including wave function analysis of the reactant complexes, intermediates, and reaction mechanism. Meantime, the effect of the solvent and noncovalent interaction on the reaction was also discussed. The obtained result was well matched with experimental data and gave a deeper understanding of the reaction. It is found that the reaction went through several cascade-reaction steps, including Aldol reaction, imine rearrangement, Michael addition reaction, and the whole reactions were equilibrium. Based on the ab initio analysis, the reaction was improved by increasing the yield with 20%.Graphical abstract

Source: Computational and Theoretical Chemistry - October 31, 2018 Category: Chemistry Source Type: research