Insights into the synthesis and structural properties of pro-chiral 2-acetyl-N-aryl-2-(prop-2-yn-1-yl)pent-4-ynamides/-2-allyl-4-enamide derivatives through kinetics and energy frameworks†

IF 3.9 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

RSC Advances Pub Date : 2025-05-12 DOI:10.1039/D5RA02166A

Disha P. Vala, Bhavesh N. Socha, Victoria G. Collins, Mehul P. Parmar, Chirag D. Patel, Savan S. Bhalodiya, Subham G. Patel, Sourav Banerjee and Hitendra M. Patel

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引用次数: 0

Abstract

In this study, we successfully synthesized a series of pro-chiral 2-acetyl-N-aryl-2-(prop-2-yn-1-yl)pent-4-ynamide/-2-allyl-4-enamide derivatives 5(a–n) starting from 4-enamide-N-(prop-2-yn-1-yl)pent-4-ynamide/-N-allyl-4-enamide 4 through a bimolecular nucleophilic substitution (S_N2) reaction. We report, for the first time, a novel C–C bond formation between allyl and acetoacetanilide derivatives, supported by detailed mechanistic analysis involving alkyne interactions. The reaction mechanism, characterized by a nucleophilic attack at the substrate's carbon center leading to displacement of the leaving group, was validated through intrinsic reaction coordinate (IRC) analysis, providing deeper insights into its pathway and dynamics.

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通过动力学和能量框架研究前手性2-乙酰基- n-芳基-2-（丙-2-yn-1-基）4-芳酰/-2-烯丙基-4-酰胺衍生物的合成和结构性质

本研究以4-enamide- n- (prop-2-yn-1-yl) p4 -ynamide/- n-烯丙基-4-enamide 4为起点，通过双分子亲核取代（SN2）反应，成功合成了一系列前手性2-乙酰基- n-芳基-2-(prop-2-yn-1-yl) p4 -ynamide/-2-烯丙基-4-enamide衍生物5（a - n）。我们首次报道了烯丙基和乙酰乙酰苯胺衍生物之间形成的一种新的C-C键，并进行了涉及炔相互作用的详细机制分析。该反应机制的特点是在底物碳中心发生亲核攻击，导致离去基位移，通过内在反应坐标（IRC）分析进行了验证，为其途径和动力学提供了更深入的了解。

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来源期刊

RSC Advances chemical sciences-

CiteScore

7.50

自引率

2.60%

发文量

3116

审稿时长

1.6 months

期刊介绍： An international, peer-reviewed journal covering all of the chemical sciences, including multidisciplinary and emerging areas. RSC Advances is a gold open access journal allowing researchers free access to research articles, and offering an affordable open access publishing option for authors around the world.