Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles |
| |
| Authors: | Nerith Rocio Elejalde-Cadena,Mayra Garcí a-Olave,David Figueroa,Pietro Vidossich,Gian Pietro Miscione,Jaime Portilla |
| |
| Affiliation: | 1.Bioorganic Compounds Research Group, Department of Chemistry, Universidad de los Andes, Carrera 1 No. 18A-10, Bogotá 111711, Colombia; (N.R.E.-C.); (M.G.-O.);2.COBO-Computational Bio-Organic Chemistry Bogotá, Department of Chemistry, Universidad de los Andes, Cra 1 No. 18A-12, Bogotá 111711, Colombia; (D.F.); (G.P.M.);3.Laboratory of Molecular Modeling and Drug Discovery, Istituto Italiano di Tecnologia, Via Morego 30, 16163 Genova, Italy; |
| |
| Abstract: | A pseudo-three-component synthesis of N-aroylmethylimidazoles 3 with three new C–N bonds formed regioselectively under microwave conditions was developed. Products were obtained by reacting two equivalents of aroylmethyl bromide (ArCOCH2Br, 1) with the appropriate amidine salt (RCN2H3.HX, 2) and with K2CO3 as a base in acetonitrile. The bicomponent reaction also occurred, giving the expected 4(5)-aryl-1H-imidazoles 4. Notably, the ratio of products 3 and 4 is governed by steric factors of the amidine 2 (i.e., R = H, CH3, Ph). Therefore, a computational study was carried out to understand the reaction course regarding product ratio (3/4), regioselectivity, and the steric effects of the amidine substituent group. |
| |
| Keywords: | amidines N-aroylmethylimidazoles DFT calculations pseudo-MCRs steric effect |
|
|
