Abstract
| Language | English |
|---|---|
| Pages | 359-371 |
| Number of pages | 13 |
| Journal | Acta Crystallographica Section C: Structural Chemistry |
| Volume | C75 |
| Issue number | Part 3 |
| Early online date | 20 Feb 2019 |
| DOIs | |
| Publication status | Published - 1 Mar 2019 |
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Keywords
- Fries rearrangement
- heterocyclic amides
- crystal structure
- amino-1,2,4-triazole
- prototropy process
- microwave-assisted reaction
- DFT
- computational chemistry
- Hirshfeld surface maps
Cite this
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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.; Arango-Daraviña, K.; Becerra, D.; Castillo, J.-C.; Kennedy, A. R.; Macías, M. A.
In: Acta Crystallographica Section C: Structural Chemistry, Vol. C75, No. Part 3, 01.03.2019, p. 359-371.Research output: Contribution to journal › Article
TY - JOUR
T1 - 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
T2 - Acta Crystallographica Section C: Structural Chemistry
AU - Moreno-Fuquen, R.
AU - Arango-Daraviña, K.
AU - Becerra, D.
AU - Castillo, J.-C.
AU - Kennedy, A. R.
AU - Macías, M. A.
PY - 2019/3/1
Y1 - 2019/3/1
N2 - 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.
AB - 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.
KW - Fries rearrangement
KW - heterocyclic amides
KW - crystal structure
KW - amino-1,2,4-triazole
KW - prototropy process
KW - microwave-assisted reaction
KW - DFT
KW - computational chemistry
KW - Hirshfeld surface maps
UR - http://journals.iucr.org/c/
U2 - 10.1107/S2053229619002572
DO - 10.1107/S2053229619002572
M3 - Article
VL - C75
SP - 359
EP - 371
JO - Acta Crystallographica Section C: Structural Chemistry
JF - Acta Crystallographica Section C: Structural Chemistry
SN - 2053-2296
IS - Part 3
ER -