Patel Manan S, Parekh Jaydeepkumar N, Chudasama Dipakkumar D, Patel Harsh C, Dalwadi Priyanka, Kunjadiya Anju, Bhatt Vaibhav, Ram Kesur R
Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388 120, Gujarat, India.
Department of Applied and Interdisciplinary Sciences (IICISST), Sardar Patel University, Vallabh Vidyanagar 388 120, Gujarat, India.
ACS Omega. 2022 Aug 18;7(34):30420-30439. doi: 10.1021/acsomega.2c03787. eCollection 2022 Aug 30.
A simple, straightforward, and energy-efficient greener route for the synthesis of a series of biologically interesting functionalized 1,1-dihomoarylmethane scaffolds has been developed in the presence of meglumine as an efficient and eco-friendly organo-catalyst via one-pot pseudo-three-component reaction at room temperature. Following this protocol, it is possible to synthesize 1,1-dihomoarylmethane scaffolds of an assortment of C-H activated acids such as dimedone, 1,3-cyclohexadione, 4-hydroxy-6-methyl-2-pyrone, 4-hydroxycoumarin, and 1-phenyl-3-methyl-pyrazolone. The salient features of the present green protocol are mild reaction conditions, good to excellent yields, operational simplicity, easy isolation of products, no cumbersome post treatment, high atom economy, and low E-factor. In addition, this chemistry portrays several green advantages including the reusability of reaction media and product scalability, which makes protocol sustainably efficient. Additionally, several control experiments such as protection of catalyst reactive site, DO exchange, and H NMR studies revealed possible pathways for meglumine-promoted reactions. Inspired by the natural physiological environment of 1,1-dihomoarylmethane scaffolds, we reconnoitered the biological profile of our compounds and synthesized compounds that were promising for their antiproliferative and antibacterial activities.
在葡甲胺作为高效且环保的有机催化剂存在下，通过室温下单锅伪三组分反应，开发了一种简单、直接且节能的绿色路线，用于合成一系列具有生物学意义的功能化1,1-二高芳基甲烷支架。按照此方案，可以合成各种C-H活化酸的1,1-二高芳基甲烷支架，如达美酮、1,3-环己二酮、4-羟基-6-甲基-2-吡喃酮、4-羟基香豆素和1-苯基-3-甲基-吡唑啉酮。本绿色方案的显著特点是反应条件温和、产率良好至优异、操作简单、产物易于分离、无需繁琐的后处理、高原子经济性和低E-因子。此外，这种化学方法还具有几个绿色优势，包括反应介质的可重复使用性和产物的可扩展性，这使得该方案具有可持续的高效性。此外，一些对照实验，如催化剂活性位点的保护、DO交换和1H NMR研究，揭示了葡甲胺促进反应的可能途径。受1,1-二高芳基甲烷支架天然生理环境的启发，我们研究了我们化合物的生物学特性，并合成了具有抗增殖和抗菌活性潜力的化合物。
