An efficient solvent-free synthesis of NH-pyrazoles from β-dimethylaminovinylketones and hydrazine on grinding

被引：61

作者：

Longhi, Kelvis ^{[1
]}

Moreira, Dayse N. ^{[1
]}

Marzari, Mara R. B. ^{[1
]}

Floss, Vagner M. ^{[1
]}

Bonacorso, Helio G. ^{[1
]}

Zanatta, Nilo ^{[1
]}

Martins, Marcos A. P. ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, Nucleo Quim Heterociclos NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 24期

关键词：

Enaminones; Pyrazoles; Grinding; Solvent-free conditions; ONE-POT SYNTHESIS; GREEN CHEMISTRY; IONIC LIQUID; BIOLOGICAL EVALUATION; KETONES; CONDENSATION; DERIVATIVES; ABSENCE; ENAMINONES; CATALYSIS;

D O I：

10.1016/j.tetlet.2010.04.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of NH-pyrazoles was efficiently synthesized from the reaction of beta-dimethylaminovinylketones ([(RC)-C-1(O)C(R-2)=CHN(Me-2)], where R-1 = Me, Ph, 3-MeO-Ph, 4-Me-Ph, 4-MeO-Ph, 4-F-Ph, 4-Cl-Ph, 4-Br-Ph, 4-O2N-Ph, fur-2-yl, thien-2-yl; R-2 = H, 2-MeO-Ph; R-1, R-2 = -(CH2)(3)C(O)-) and hydrazine sulfate in solid state on grinding in the presence of p-toluenesulfonic acid (PTSA). Most of the reactions proceeded smoothly at room temperature under solvent-free conditions. In comparison with the classical reaction conditions, which employ molecular solvent (ethanol), this new synthetic method has the advantages of shorter times, higher yields, mild reaction conditions as well as being environmentally friendly. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3193 / 3196

页数：4

共 52 条

[21] Ultrasound promoted synthesis of 5-hydroxy-5-trihalomethyl-4,5-dihydroisoxazoles and β-enamino trihalomethyl ketones in water [J].

Martins, MAP ;

Pereira, CMP ;

Cunico, W ;

Moura, S ;

Rosa, FA ;

Peres, RL ;

Machado, P ;

Zanatta, N ;

Bonacorso, HG .

ULTRASONICS SONOCHEMISTRY, 2006, 13 (04) :364-370

[22] Microwave-assisted synthesis of novel 5-trichloromethyl-4,5-dihydro-1H-1-pyrazole methyl esters under solvent free conditions [J].

Martins, MAP ;

Beck, P ;

Machado, P ;

Brondani, S ;

Moura, S ;

Zanatta, N ;

Bonacorso, HG ;

Flores, AFC .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2006, 17 (02) :408-411

[23] Simplified approach to the regiospecific synthesis of trichloromethylpyrazolines using microwave irradiation [J].

Martins, Marcos A. P. ;

Muraro, Paulo ;

Beck, Paulo ;

Machado, Pablo ;

Frizzo, Clarissa P. ;

Zanatta, Nilo ;

Bonacorso, Helio G. .

SYNTHETIC COMMUNICATIONS, 2008, 38 (20) :3465-3476

[24] An ionic liquid as reaction medium for the synthesis of halo-containing β-enaminones at room temperature [J].

Martins, Marcos A. P. ;

Guarda, Emerson A. ;

Frizzo, Clarissa P. ;

Marzari, Mara R. B. ;

Moreira, Dayse N. ;

Zanatta, Nilo ;

Bonacorso, Helio G. .

MONATSHEFTE FUR CHEMIE, 2008, 139 (11) :1321-1327

[25] Synthesis of β-enaminones by ionic liquid catalysis:: A one-pot condensation under solvent-free conditions [J].

Martins, Marcos A. P. ;

Frizzo, Clarissa P. ;

Moreira, Dayse N. ;

Rosa, Fernanda A. ;

Marzari, Mara R. B. ;

Zanatta, Nilo ;

Bonacorso, Helio G. .

CATALYSIS COMMUNICATIONS, 2008, 9 (06) :1375-1378

[26] A solvent-free synthesis of β-enamino trihalomethyl ketones [J].

Martins, Marcos A. P. ;

Peres, Rodrigo L. ;

Fiss, Gabriela F. ;

Dimer, Frantiescoli A. ;

Mayer, Rodrigo ;

Frizzo, Clarissa P. ;

Marzari, Mara R. B. ;

Zanatta, Nilo ;

Bonacorso, Helio G. .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2007, 18 (08) :1486-1491

[27] Microwave assisted regiospecific synthesis of 5-trifluoromethyl-4,5-dihydropyrazoles and pyrazoles [J].

Martins, Marcos A. P. ;

Pereira, Claudio M. P. ;

Moura, Sidnei ;

Frizzo, Clarissa P. ;

Beck, Paulo ;

Zanatta, Nilo ;

Bonacorso, Helio G. ;

Flores, Alex F. C. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (05) :1195-1199

[28] Solvent-free Route to β-Enamino Dichloromethyl Ketones and Application in the Synthesis of Novel 5-Dichloromethyl-1H-pyrazoles [J].

Martins, Marcos A. P. ;

Peres, Rodrigo L. ;

Frizzo, Clarissa P. ;

Scapin, Elisandra ;

Moreira, Dayse N. ;

Fiss, Gabriela F. ;

Zanatta, Nilo ;

Bonacorso, Helio G. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (06) :1247-1251

[29] Solvent-Free Heterocyclic Synthesis [J].

Martins, Marcos A. P. ;

Frizzo, Clarissa P. ;

Moreira, Dayse N. ;

Buriol, Lilian ;

Machado, Pablo .

CHEMICAL REVIEWS, 2009, 109 (09) :4140-4182

[30] A simple, modular method for the synthesis of 3,4,5-trisubstituted pyrazoles [J].

McLaughlin, Mark ;

Marcantonio, Karen ;

Chen, Cheng-yi ;

Davies, Ian W. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (11) :4309-4312

← 1 2 3 4 5 6 →