Synthesis of Functionalized Thiophene Based Pyrazole Amides via Various Catalytic Approaches: Structural Features through Computational Applications and Nonlinear Optical Properties

Iram Kanwal and Nasir Rasool and Syeda Huda Mehdi Zaidi and Zainul Amiruddin Zakaria and Muhammad Bilal and Muhammad Ali Hashmi and Adeel Mubarik and Gulraiz Ahmad and Syed Adnan Ali Shah (2022) Synthesis of Functionalized Thiophene Based Pyrazole Amides via Various Catalytic Approaches: Structural Features through Computational Applications and Nonlinear Optical Properties. Molecules, 27. pp. 1-19. ISSN 1420-3049

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URL: https://www.mdpi.com/1420-3049/27/2/360

Abstract

In the present study, pyrazole-thiophene-based amide derivatives were synthesized by different methodologies. Here, 5-Bromothiophene carboxylic acid (2) was reacted with substituted, unsubstituted, and protected pyrazole to synthesize the amide. It was observed that unsubstituted amide (5-bromo-N-(5-methyl-1H-pyrazol-3-yl) thiophene-2-carboxamide (7) was obtained at a good yield of about 68 percent. The unsubstituted amide (7) was arylated through Pd (0)-catalyzed Suzuki–Miyaura cross-coupling, in the presence of tripotassium phosphate (K3PO4 ) as a base, and with 1,4-dioxane as a solvent. Moderate to good yields (66–81%) of newly synthesized derivatives were obtained. The geometry of the synthesized compounds (9a–9h) and other physical properties, like non-linear optical (NLO) properties, nuclear magnetic resonance (NMR), and other chemical reactivity descriptors, including the chemical hardness, electronic chemical potential, ionization potential, electron affinity, and electrophilicity index have also been calculated for the synthesized compounds. In this study, DFT calculations have been used to investigate the electronic structure of the synthesized compounds and to compute their NMR data. It was also observed that the computed NMR data manifested significant agreement with the experimental NMR results. Furthermore, compound (9f) exhibits a better non-linear optical response compared to all other compounds in the series. Based on frontier molecular orbital (FMO) analysis and the reactivity descriptors, compounds (9c) and (9h) were predicted to be the most chemically reactive, while (9d) was estimated to be the most stable among the examined series of compounds.

Item Type:	Article
Keyword:	Pyrazole , Amides , Arylation , Palladium , Cross-coupling , Computational
Subjects:	Q Science > QD Chemistry > QD1-999 Chemistry R Medicine > R Medicine (General) > R5-920 Medicine (General)
Department:	FACULTY > Faculty of Medicine and Health Sciences
Depositing User:	SITI AZIZAH BINTI IDRIS -
Date Deposited:	16 Jun 2022 11:39
Last Modified:	16 Jun 2022 11:39
URI:	https://eprints.ums.edu.my/id/eprint/32798

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