Reactions of β-methoxyvinyl trifluoromethyl ketones with 2-pyridinecarboxamidrazone A convenient route to trifluoromethylated 4,5-dihydro-1H-1-picolinoylpyrazole hydrochlorides

被引：21

作者：

Bonacorso, HG ^{[1
]}

Lewandowski, H ^{[1
]}

Drekener, RL ^{[1
]}

Costa, MB ^{[1
]}

Pereira, CMP ^{[1
]}

Wastowski, AD ^{[1
]}

Peppe, C ^{[1
]}

Martins, MAP ^{[1
]}

Zanatta, N ^{[1
]}

机构：

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

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2003年 / 122卷 / 02期

关键词：

enones; amidrazones; pyrazoles; hydrochlorides; Cl-35; NMR;

D O I：

10.1016/S0022-1139(03)00057-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new series of six 3-aryl-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-1-picolinoylpyrazole hydrochlorides were synthesised in one-step in high yields by the reaction of beta-methoxyvinyl trifluoromethyl ketones with 2-pyridinecarboxamidrazone in the presence of hydrochloric acid. The hydrochloride salts were easily converted to the respective new series of free trifluoromethylated 4,5-dihydro-1H-1-picolinoylpyrazoles using triethylamine in anhydrous diethyl ether. X-ray structure and Cl-35 NMR data from the pyrazole hydrochlorides are reported. (C) 2003 Elsevier Science B.V. All rights reserved.

引用

页码：159 / 163

页数：5

共 38 条

[1] Synthesis of trifluoromethylpyrroles and related heterocycles from 4-ethyloxy-1,1,1-trifluorobut-3-ene-2-one [J].

Andrew, RJ ;

Mellor, JM .

TETRAHEDRON, 2000, 56 (37) :7267-7272

[2] Stereoselective synthesis of substituted bicyclo-[3.3.1]-nonan-9-ones by additions of enamines of cyclohexanones to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one [J].

Andrew, RJ ;

Mellor, JM ;

Reid, G .

TETRAHEDRON, 2000, 56 (37) :7255-7260

[3]

BANFI E, 1993, J CHEMOTHERAPY, V5, P164

[4]

Banfi E, 1991, J Chemother, V3 Suppl 1, P66

[5] Haloacetylated enol ethers 10.: Condensation of β-alkoxyvinyl trifluoromethyl ketones with thiosemicarbazide.: Synthesis of new trifluoromethyl 4,5-dihydro-1H-1-pyrazolethiocarboxyamides [J].

Bonacorso, HG ;

Wastowski, AD ;

Zanatta, N ;

Martins, MAP ;

Naue, JA .

JOURNAL OF FLUORINE CHEMISTRY, 1998, 92 (01) :23-26

[6]

Bonacorso HG, 2002, SYNTHESIS-STUTTGART, P1079

[7] Reactions of β-alkoxyvinyl trifluoromethyl ketones.: The synthesis of N-[1-aryl-3-oxo-4,4,4-trifluoro-1-buten-1-yl]-o-phenylenediamines and 4-aryl-2-trifluoromethyl-3H-1,5-benzodiazepines [J].

Bonacorso, HG ;

Marques, LML ;

Zanatta, N ;

Martins, MAP .

SYNTHETIC COMMUNICATIONS, 2002, 32 (20) :3225-3232

[8]

Bonacorso HG, 2002, SYNTHESIS-STUTTGART, P1037

[9]

Bonacorso HG, 2001, SYNTHESIS-STUTTGART, P1505

[10]

Bonacorso HG, 2000, SYNTHESIS-STUTTGART, P1431

← 1 2 3 4 →