Evaluation of the synthesis of 1-(pentafluorophenyl)-4,5-dihydro-1H-pyrazoles using green metrics

被引：5
|
作者：
Martins, Marcos A. P. [1 ]
Beck, Paulo H. [1 ]
Buriol, Lilian [1 ]
Frizzo, Clarissa P. [1 ]
Moreira, Dayse N. [1 ]
Marzari, Mara R. B. [1 ]
Zanatta, Marcileia [1 ]
Machado, Pablo [1 ]
Zanatta, Nilo [1 ]
Bonacorso, Helio G. [1 ]
机构：
[1] Univ Fed Santa Maria, Dept Chem, Nucleo Quim Heterociclos NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil
来源：
MONATSHEFTE FUR CHEMIE | 2013年 / 144卷 / 07期
关键词：
Pyrazoles; Atom economy; Reaction mass efficiency; E-factor; Green chemistry; IONIC LIQUIDS; SOLVENT; SUSTAINABILITY; OPTIMIZATION; CHEMISTRY;
D O I：
10.1007/s00706-013-0930-x
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
1-(Pentafluorophenyl)-4,5-dihydro-1H-pyrazoles were synthesized from the cyclocondensation reactions of 4-alkoxy-1,1,1-trihalo-3-alken-2-ones (CX3C(O)CH=C(R-1)OR, where X = F, Cl; R = Me, Et; R-1 = H, Me, Et, n-Pr, i-Pr, n-Bu, i-Pent, Ph, 4-Cl-C6H4, 4-Br-C6H4, 4-F-C6H4) with pentafluorophenyl hydrazine. Pyrazoles were obtained under microwave irradiation in solvent-free conditions or under conventional heating in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIM][BF4]. These procedures furnished products in moderate to good yields in a short reaction time. Atom economy, reaction mass efficiency (RME), and environmental factor (E-factor) were determined for the cyclocondensation reaction performed under microwave (MW)/solvent-free and under conventional thermal heating/[BMIM][BF4] conditions. RME and E-factor indicated that the solvent-free procedure is invariably less green than [BMIM][BF4] when the isolated product was considered.
引用
收藏
页码：1043 / 1050
页数：8
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