Kabachnik-Fields Reaction by Mechanochemistry: New Horizons from Old Methods

被引:22
作者
Fiore, Cecilia [1 ,2 ,3 ,4 ]
Sovic, Irena [5 ]
Lukin, Stipe [5 ]
Halasz, Ivan [5 ]
Martina, Katia [2 ,3 ]
Delogu, Francesco [8 ]
Ricci, Pier Carlo [6 ]
Porcheddu, Andrea [7 ]
Shemchuk, Oleksii [4 ]
Braga, Dario [4 ]
Pirat, Jean-Luc [1 ]
Virieux, David [1 ]
Colacino, Evelina [1 ]
机构
[1] Univ Montpellier, ENSCM, CNRS, ICGM, Montpellier, France
[2] Univ Torino, Dipartimento Sci & Tecnol Farmaco, I-10125 Turin, Italy
[3] Univ Torino, NIS, I-10125 Turin, Italy
[4] Univ Bologna, Mol Crystal Engn Lab, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[5] Rudjer Boskovic Inst, Div Phys Chem, Zagreb 10000, Croatia
[6] Univ Cagliari, Dept Phys, I-09042 Monserrato, CA, Italy
[7] Univ Cagliari, Dept Chem & Geol Sci, I-09042 Monserrato, CA, Italy
[8] Univ Cagliari, Dept Mech Chem & Mat Engn, I-09123 Cagliari, Italy
关键词
alpha-Aminophosphonates; Domino reactions; Kabachnik-Fields reaction; Mechanochemistry; Raman in situ monitoring; Kinetics; Solid-state characterization; ONE-POT SYNTHESIS; ALPHA-AMINOPHOSPHONATES; SOLVENT-FREE; MEDICINAL MECHANOCHEMISTRY; ORGANOPHOSPHORUS COMPOUNDS; CRYSTAL-STRUCTURE; REAL-TIME; MECHANISM; CATALYST; ACID;
D O I
10.1021/acssuschemeng.0c05744
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
alpha-Aminophosphonates are an important class of biologically active compounds, attracting considerable attention in medicinal chemistry, by inhibiting enzymes involved in amino acid metabolism. Herein, the Kabachnik-Fields domino reaction was investigated by mechanochemistry for the first-time preparation of alpha-aminophosphonate derivatives in high yields and with full selectivity, outperforming comparable solution procedures. The reaction occurs without the addition of any external catalyst, possibly via a metal-mediated process occurring on the surface of the jar (zirconium oxide was used as the milling media). The mechanism of the mechanochemical reaction was also investigated by in situ Raman spectroscopy, and the kinetic behavior was disclosed. The solid-state structures of two representative compounds have been determined by single-crystal X-ray diffraction.
引用
收藏
页码:18889 / 18902
页数:14
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