Synthesis of bromodifluoromethyl substituted pyrazoles and isoxazoles

被引：11

作者：

Yang, Xueyan ^{[2
,3
]}

Shui, Shengxia ^{[2
,3
]}

Chen, Xi ^{[2
,3
]}

He, Hai'ou ^{[2
,3
]}

Wu, Fanhong ^{[1
,2
,3
,4
]}

机构：

[1] Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai 200235, Peoples R China

[2] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[3] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[4] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin, Peoples R China

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2010年 / 131卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Bromodifluoromethyl; Pyrazoles; Isoxazoles; Regioselectivity; Synthesis; TRIFLUOROMETHYL-BETA-DIKETONES; INHIBITORS; HETEROCYCLES; DESIGN;

D O I：

10.1016/j.jfluchem.2009.12.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 [无机化学];

摘要：

Bromodifluoromethyl substituted beta-diketone 3a-3d, prepared from corresponding ketones and ethyl bromodifluoroactate in the presence of sodium methoxide, reacted with aryl hydrazine derivatives affording bromodifluoromethyl substituted pyrazoles in high regioselectivity. The reaction of 3a-3d with hydroxylamine hydrochloride gave dihydroisoxazoles, which afforded bromodifluoromethyl substituted isoxazoles through dehydration by PPA or concentrated sulfuric acid. (C) 2010 Published by Elsevier B.V.

引用

收藏

页码：426 / 432

页数：7

相关论文

共 26 条

[1]

Copper-mediated reaction of 2-halopyridines with ethyl bromodifluoroacetate [J].

Ashwood, MS ;

Cottrell, IF ;

Cowden, CJ ;

Wallace, DJ ;

Davies, AJ ;

Kennedy, DJ ;

Dolling, UH .

TETRAHEDRON LETTERS, 2002, 43 (50) :9271-9273

[2]

Tetrakis(dimethylamino)ethylene as a useful reductant of some bromodifluoromethyl heterocycles.: Application to the synthesis of new gem-difluorinated heteroarylated compounds [J].

Burkholder, C ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5385-5394

[3]

Synthesis and reactivity of halogeno-difluoromethyl aromatics and heterocycles -: Application to the synthesis of gem-difluorinated bioactive compounds [J].

Burkholder, CR ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF FLUORINE CHEMISTRY, 2001, 109 (01) :39-48

[4]

The syntheses of nonnucleoside, HIV-1 reverse transcriptase inhibitors containing a CF2 group -: The SRN1 reactions of 2-(bromodifluoromethyl)benzoxazole with the anions derived from heterocyclic thiols and phenolic compounds [J].

Burkholder, CR ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF FLUORINE CHEMISTRY, 2000, 102 (1-2) :369-376

[5]

Fluorinated heterocyclic compounds.: An effective strategy for the synthesis of fluorinated Z-oximes of 3-perfluoroalkyl-6-phenyl-2H-1,2,4-triazin5-ones via a ring-enlargement reaction of 3-benzoyl-5-perfluoroalkyl-1,2,4-oxadiazoles and hydrazine [J].

Buscemi, S ;

Pace, A ;

Piccionello, AP ;

Macaluso, G ;

Vivona, N ;

Spinelli, D ;

Giorgi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3288-3291

[6]

Design, synthesis, and antipicornavirus activity of 1-[5-(4-arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one derivatives [J].

Chang, CS ;

Lin, YT ;

Shih, SR ;

Lee, CC ;

Lee, YC ;

Tai, CL ;

Tseng, SN ;

Chern, JH .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (10) :3522-3535

[7]

Effects of isoxazole herbicides on protoporphyrinogen oxidase and porphyrin physiology [J].

Dayan, FE ;

Duke, SO ;

Reddy, KN ;

Hamper, BC ;

Leschinsky, KL .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (03) :967-975

[8]

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

[9]

SYNTHESIS AND HERBICIDAL ACTIVITY OF 3-ARYL-5-(HALOALKYL)-4-ISOXAZOLECARBOXAMIDES AND THEIR DERIVATIVES [J].

HAMPER, BC ;

LESCHINSKY, KL ;

MASSEY, SS ;

BELL, CL ;

BRANNIGAN, LH ;

PROSCH, SD .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1995, 43 (01) :219-228

[10]

Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-4-phenyl-3-trifluoromethylpyrazoles [J].

Kumar, V ;

Aggarwal, R ;

Tyagi, P ;

Singh, SP .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (09) :922-927