Haloacetylated enol ethers: 16[5] regiospecific synthesis of 5-trichloromethyl-pyrazoles

被引：31

作者：

Flores, AFC ^{[1
]}

Martines, MAP ^{[1
]}

Rosa, A ^{[1
]}

Flores, DC ^{[1
]}

Zanatta, N ^{[1
]}

Bonacorsso, HG ^{[1
]}

机构：

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

来源：

SYNTHETIC COMMUNICATIONS | 2002年 / 32卷 / 10期

关键词：

pyrazoles; cyclocondensations; trichloromethyl ketones;

D O I：

10.1081/SCC-120004150

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiospecific synthesis and isolation of three series of 5-trichloromethyl-pyrazoles 2f-j, 3a-j and 4a-j from the cyclo-condensation of 1,1,1-trichloro-4-alkoxy-3-alken-2-ones (1a-f) or trichloroacetyl containing beta-diketones (1g-j) with dry hydrazine and phenyl-hydrazine is reported. It was established by H-1- and C-13-NMR spectroscopy that the 5-hydroxy-5-trichloromethyl-4,5-dihydro-1H-pyrazole intermediates 2a-j were formed quantitatively.

引用

页码：1585 / 1594

页数：10

共 21 条

[1] Haloacetylated enol ethers:: 12 [18].: Regiospecific synthesis and structural determination of stable 5-hydroxy-1H-pyrazolines [J].

Bonacorso, HG ;

Oliveira, MR ;

Wentz, AP ;

Wastowski, AD ;

de Oliveira, AB ;

Höerner, M ;

Zanatta, N ;

Martins, MAP .

TETRAHEDRON, 1999, 55 (02) :345-352

[2] A convenient method for the synthesis of 2-trichloromethyl-4-p-substituted-phenyl-3H-1,5-benzodiazepines. [J].

Bonacorso, HG ;

Bittencourt, ST ;

Wastowski, AD ;

Wentz, AP ;

Zanatta, N ;

Martins, MAP .

TETRAHEDRON LETTERS, 1996, 37 (51) :9155-9156

[3] HALOACETYLATED ENOL ETHERS .2. SYNTHESIS OF 5-TRIFLUOROMETHYLPYRAZOLES [J].

BRAIBANTE, MEF ;

CLAR, G ;

MARTINS, MAP .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (04) :1159-1160

[4]

BUSH W, 1976, CHEM ABSTR 123914F, V85

[5]

KATRIZKY, 1995, COMPREHENSIVE HETERO, V1

[6] CHEMISTRY OF CHLORAL [J].

LUKNITSKII, FI .

CHEMICAL REVIEWS, 1975, 75 (03) :259-289

[7] Trellis based code combining protocols for Reed-Muller codes [J].

Martin, I ;

Honary, B .

ELECTRONICS LETTERS, 2000, 36 (03) :217-218

[8]

Martins M.A.P., 1994, QUIM NOVA, V17, P298

[9] Molecular structure of heterocycles: 3. Semiempirical MO calculations and Karplus-type dihedral angle dependence for the coupling constant relationship of some 4,5-dihydro-5-hydroxy-5(3)-halomethylisoxazoles [J].

Martins, MAP ;

Zoch, AN ;

Zanatta, N ;

Flores, AFC .

SPECTROSCOPY LETTERS, 1998, 31 (03) :621-631

[10] HALOACETYLATED ENOL ETHERS .3. SYNTHESIS OF 3,3A,4,5,6,7-HEXAHYDRO-3-HALOMETHY[2,1]BENZOISOXAZOLES [J].

MARTINS, MAP ;

FLORES, AFC ;

FREITAG, R ;

ZANATTA, N .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (03) :731-733

← 1 2 3 →