Catalyst- and solvent-free synthesis of 2-fluoro-N- (3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide through a microwave-assisted Fries rearrangement : X-ray structural and theoretical studies
Moreno-Fuquen, R. and Arango-Daraviña, K. and Becerra, D. and Castillo, J.-C. and Kennedy, A. R. and Macías, M. A. (2019) Catalyst- and solvent-free synthesis of 2-fluoro-N- (3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide through a microwave-assisted Fries rearrangement : X-ray structural and theoretical studies. Acta Crystallographica Section C: Structural Chemistry, C75 (Part 3). pp. 359-371. ISSN 2053-2296 (https://doi.org/10.1107/S2053229619002572)
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Abstract
An efficient approach for the regioselective synthesis of (5-amino-3-methylsulfanyl- 1H-1,2,4-triazol-1-yl)(2-fluorophenyl)methanone, C10H9FN4OS, (3), from the N-acylation of 3-amino-5-methylsulfanyl-1H-1,2,4-triazole, (1), with 2-fluorobenzoyl chloride has been developed. Heterocyclic amide (3) was used successfully as a strategic intermediate for the preparation of 2-fluoro-N-(3- methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide, C10H9FN4OS, (4), through a microwave-assisted Fries rearrangement under catalyst- and solvent-free conditions. Theoretical studies of the prototropy process of (1) and the Fries rearrangement of (3) to provide (4), involving the formation of an intimate ion pair as the key step, were carried out by density functional theory (DFT) calculations. The crystallographic analysis of the intermolecular interactions and the energy frameworks based on the effects of the different molecular conformations of (3) and (4) are described.
ORCID iDs
Moreno-Fuquen, R., Arango-Daraviña, K., Becerra, D., Castillo, J.-C., Kennedy, A. R. ORCID: https://orcid.org/0000-0003-3652-6015 and Macías, M. A.;-
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Item type: Article ID code: 67299 Dates: DateEvent1 March 2019Published20 February 2019Published Online20 February 2019AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 14 Mar 2019 10:17 Last modified: 30 Sep 2024 00:26 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/67299