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

[11] Green Chemistry: challenges and opportunities [J].

Clark, JH .

GREEN CHEMISTRY, 1999, 1 (01) :1-8

[12] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[13] 3,5-bis(trifluoromethyl)pyrazoles: A novel class of NFAT transcription factor regulator [J].

Djuric, SW ;

BaMaung, NY ;

Basha, A ;

Liu, HQ ;

Luly, JR ;

Madar, DJ ;

Sciotti, RJ ;

Tu, NP ;

Wagenaar, FL ;

Wiedeman, PE ;

Zhou, X ;

Ballaron, S ;

Bauch, J ;

Chen, YW ;

Chiou, XG ;

Fey, T ;

Gauvin, D ;

Gubbins, E ;

Hsieh, GC ;

Marsh, KC ;

Mollison, KW ;

Pong, M ;

Shaughnessy, TK ;

Sheets, MP ;

Smith, M ;

Trevillyan, JM ;

Warrior, U ;

Wegner, CD ;

Carter, GW .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (16) :2975-2981

[14]

Fan W.-Q., 1996, COMPREHENSIVE HETERO, V4, P1, DOI [DOI 10.1016/B978-008096518-5.00059-9, 10.1016/b978-008096518-5.00059-9]

[15] Grindstone chemistry: one-pot synthesis of spiro[diindenopyridine-indoline]triones and spiro[acenaphthylene-diindenopyridine]triones [J].

Ghahremanzadeh, Ramin ;

Ahadi, Somayeh ;

Shakibaei, Ghazaleh Imani ;

Bazgir, Ayoob .

TETRAHEDRON LETTERS, 2010, 51 (03) :499-502

[16] N-ALKYLATION AND N-ARYLATION OF UNSYMMETRICAL PYRAZOLES [J].

GRIMMETT, MR ;

LIM, KHR ;

WEAVERS, RT .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (10) :2203-2213

[17]

*HYP INC, 2007, HYPERCHEM PROF 8 06

[18]

Katritzky A.R., 1996, COMPREHENSIVE HETERO, V3

[19] An efficient, catalyst- and solvent-free, four-component, and one-pot synthesis of polyhydroquinolines on grinding [J].

Kumar, Satish ;

Sharma, Poonam ;

Kapoor, Kamal K. ;

Hundal, Maninder Singh .

TETRAHEDRON, 2008, 64 (03) :536-542

[20] Synthesis and structure of novel 4,5-dihydro-1H-pyrazoles:: salicylic acid based analgesic agents [J].

Machado, Pablo ;

Rosa, Fernanda A. ;

Rossatto, Marcelo ;

Sant'Anna, Gabriela da S. ;

Sauzem, Patricia D. ;

da Silva, Rubia M. Siqueira ;

Rubin, Maribel A. ;

Ferreira, Juliano ;

Bonacorso, Helio G. ;

Zanatta, Nilo ;

Martinsa, Marcos A. P. .

ARKIVOC, 2007, :281-297

← 1 2 3 4 5 6 →