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

页码：1043 / 1050

页数：8

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