Department of Chemistry, Faculty of Superior Studies Cuautitlan, Field 1, Autonomous National University of Mexico, Cuautitlan Izcalli, State of Mexico, 54740, Mexico.
Int J Mol Sci. 2013 Jan 30;14(2):2903-15. doi: 10.3390/ijms14022903.
Multicomponent reactions are excellent methods that meet the requirements of green chemistry, by reducing the number of steps, and consequently reducing purification requirements. Accordingly, in this work, 11 novel hybrid-boron-containing molecules, namely eight 1,4-dihydropyridines and three 3,4-dihydropyrimidinones, derived from formylphenylboronic acids (ortho, meta and para), were obtained using a green approach, involving H-4CR and B-3CR practices, in the presence of ethanol, which is a green solvent, and using three comparatively different modes of activation (mantle heating, yield 3%-7% in 24 h, Infrared Radiation (IR) irradiation, yield 12%-17% in 12 h, and microwave irradiation, yield 18%-80%, requiring very low reaction times of 0.25-0.33 h). In addition, as a green-approach is offered, a convenient analysis, of the 12 green chemistry principles for the overall procedure was performed. Finally, since all the products are new, characterizations were carried out using common analytic procedures (1H, 11B, and 13C NMR, FAB+MS, HRMS, and IR). The accurate mass data of unexpected ions related to interactions between thioglycerol and the expected products, in the FAB+-mode, enabled unequivocal characterization of the target molecules.
多组分反应是一种优秀的方法，通过减少步骤数，从而满足绿色化学的要求，并降低了对纯化的要求。因此，在这项工作中，使用了一种绿色方法，在乙醇存在的情况下，通过 H-4CR 和 B-3CR 实践，获得了 11 种新型的含硼杂合分子，即 8 种 1,4-二氢吡啶和 3 种 3,4-二氢嘧啶酮，这些分子源自醛基苯基硼酸（邻位、间位和对位）。乙醇是一种绿色溶剂，使用了三种相对不同的激活模式（套加热、红外辐射（IR）辐射和微波辐射）。套加热的产率为 3%-7%，需要 24 小时；IR 辐射的产率为 12%-17%，需要 12 小时；微波辐射的产率为 18%-80%，需要非常短的反应时间 0.25-0.33 小时。此外，由于提供了一种绿色方法，对整个过程的 12 条绿色化学原则进行了方便的分析。最后，由于所有的产物都是新的，所以使用常见的分析程序（1H、11B 和 13C NMR、FAB+MS、HRMS 和 IR）对其进行了表征。在 FAB+-模式下，与硫甘油之间的相互作用相关的意想不到的离子的精确质量数据，使得目标分子的特征化变得明确。
