Bioorganic Compounds Research Group, Department of Chemistry, Universidad de los Andes, Carrera 1 No. 18A-10, Bogotá 111711, Colombia.
COBO-Computational Bio-Organic Chemistry Bogotá, Department of Chemistry, Universidad de los Andes, Cra 1 No. 18A-12, Bogotá 111711, Colombia.
Molecules. 2022 Feb 9;27(4):1165. doi: 10.3390/molecules27041165.
A pseudo-three-component synthesis of -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 (ArCOCHBr, ) with the appropriate amidine salt (RCNH.HX, ) and with KCO as a base in acetonitrile. The bicomponent reaction also occurred, giving the expected 4(5)-aryl-1-imidazoles . Notably, the ratio of products and is governed by steric factors of the amidine (i.e., R = H, CH, Ph). Therefore, a computational study was carried out to understand the reaction course regarding product ratio (/), regioselectivity, and the steric effects of the amidine substituent group.
发展了一种在微波条件下通过三个新的 C-N 键形成的 -芳基甲酰基咪唑的伪三组分合成方法，具有区域选择性。通过将当量的芳基甲酰基溴（ArCOCHBr， ）与适当的脒盐（RCNH.HX， ）和 KCO 作为碱在乙腈中反应，得到产物。双组分反应也发生了，得到了预期的 4(5)-芳基-1-咪唑。值得注意的是，产物 和 的比例受脒的空间因素（即，R = H，CH，Ph）的控制。因此，进行了计算研究以了解关于产物比例（/）、区域选择性和脒取代基的空间效应的反应过程。
