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

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

doi:10.1039/D5RA02166A

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

Disha P. Vala
, Bhavesh N. Socha
, Victoria G. Collins
, Mehul P. Parmar
, Chirag D. Patel
, Savan S. Bhalodiya
, Subham G. Patel
, Sourav Banerjee (Lead / Corresponding author)
, Hitendra M. Patel (Lead / Corresponding author)

Research output: Contribution to journal › Article › peer-review

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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 (SN2) reaction. We report, for the first time, a novel C-C bond formation between allyl and acetoacetanilide derivatives, supported by a 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 insight into its pathway and dynamics.

Original language	English
Pages (from-to)	15712-15723
Number of pages	12
Journal	RSC Advances
Volume	15
Early online date	12 May 2025
DOIs	https://doi.org/10.1039/D5RA02166A
Publication status	E-pub ahead of print - 12 May 2025

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10.1039/D5RA02166ALicence: CC BY

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A Single Kinase Modulates The Diverse Extracellular Phosphoproteome Of Glioblastoma Multiforme
Banerjee, S. (Investigator)
1/08/22 → 31/07/26
Project: Research

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Vala, D. P., Socha, B. N., Collins, V. G., Parmar, M. P., Patel, C. D., Bhalodiya, S. S., Patel, S. G., Banerjee, S., & Patel, H. M. (2025). 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. RSC Advances, 15, 15712-15723. Advance online publication. https://doi.org/10.1039/D5RA02166A

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title = "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",

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 (SN2) reaction. We report, for the first time, a novel C-C bond formation between allyl and acetoacetanilide derivatives, supported by a 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 insight into its pathway and dynamics.",

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

year = "2025",

month = may,

day = "12",

doi = "10.1039/D5RA02166A",

language = "English",

volume = "15",

pages = "15712--15723",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

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Vala, DP, Socha, BN, Collins, VG, Parmar, MP, Patel, CD, Bhalodiya, SS, Patel, SG, Banerjee, S & Patel, HM 2025, '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', RSC Advances, vol. 15, pp. 15712-15723. https://doi.org/10.1039/D5RA02166A

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. / Vala, Disha P.; Socha, Bhavesh N.; Collins, Victoria G. et al.
In: RSC Advances, Vol. 15, 12.05.2025, p. 15712-15723.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 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

AU - Vala, Disha P.

AU - Socha, Bhavesh N.

AU - Collins, Victoria G.

AU - Parmar, Mehul P.

AU - Patel, Chirag D.

AU - Bhalodiya, Savan S.

AU - Patel, Subham G.

AU - Banerjee, Sourav

AU - Patel, Hitendra M.

PY - 2025/5/12

Y1 - 2025/5/12

N2 - 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 (SN2) reaction. We report, for the first time, a novel C-C bond formation between allyl and acetoacetanilide derivatives, supported by a 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 insight into its pathway and dynamics.

AB - 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 (SN2) reaction. We report, for the first time, a novel C-C bond formation between allyl and acetoacetanilide derivatives, supported by a 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 insight into its pathway and dynamics.

U2 - 10.1039/D5RA02166A

DO - 10.1039/D5RA02166A

M3 - Article

SN - 2046-2069

VL - 15

SP - 15712

EP - 15723

JO - RSC Advances

JF - RSC Advances

ER -

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

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A Single Kinase Modulates The Diverse Extracellular Phosphoproteome Of Glioblastoma Multiforme

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