Regioselective synthesis of 1,3,5-tri- and 1,3,4,5-tetrasubstituted pyrazoles from N-arylhydrazones and nitroolefins

被引：134

作者：

Deng, Xiaohu ^{[1
]}

Mani, Neelakandha S. ^{[1
]}

机构：

[1] Johnson & Johnson Pharmaceut Res & Dev LLC, San Diego, CA 92121 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 06期

关键词：

D O I：

10.1021/jo7026195

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Two general protocols are developed for the regioselective synthesis of 1,3,5-tri- and 1,3,4,5-tetrasubstituted pyrazoles by the reaction of electron-deficient N-arylhydrazones with nitroolefins. Studies on the stereochemistry of the key pyrazolidine intermediate suggest a stepwise cycloaddition mechanism.

引用

页码：2412 / 2415

页数：4

共 35 条

[1]

[Anonymous], BER

[2]

[Anonymous], 2002, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products

[3] Efficient tautomerization hydrazone-azomethine imine under microwave irradiation.: Synthesis of [4,3′] and [5,3′]bipyrazoles [J].

Arrieta, A ;

Carrillo, JR ;

Cossío, FP ;

Díaz-Ortiz, A ;

Gómez-Escalonilla, MJ ;

de la Hoz, A ;

Langa, F ;

Moreno, A .

TETRAHEDRON, 1998, 54 (43) :13167-13180

[4] Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents [J].

Bekhit, AA ;

Abdel-Aziem, T .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (08) :1935-1945

[5] Regioselective synthesis of 1,3,5-substituted pyrazoles from acetylenic ketones and hydrazines [J].

Bishop, BC ;

Brands, KMJ ;

Gibb, AD ;

Kennedy, DJ .

SYNTHESIS-STUTTGART, 2004, (01) :43-52

[6] STEREOSPECIFICITY OF 1,3-DIPOLAR CYCLOADDITIONS OF CYCLIC NITRONES TO (E) AND (Z)-BETA-NITROSTYRENES [J].

BURDISSO, M ;

GAMBA, A ;

GANDOLFI, R ;

PEVARELLO, P .

TETRAHEDRON, 1987, 43 (08) :1835-1846

[7] Reaction of N-monosubstituted hydrazones with nitroolefins:: A novel regioselective pyrazole synthesis [J].

Deng, Xiaohu ;

Mani, Neelakandha S. .

ORGANIC LETTERS, 2006, 8 (16) :3505-3508

[8]

Elguero J., 2002, TARGETS HETEROCYCL S, V6, P52, DOI DOI 10.12691/WJOC-5-1-4

[9]

Gomez-Guillen M., 1988, CARBOHYD RES, V180, P1

[10] NEW PENTAHYDROXYPENTYLPYRAZOLES FROM THE REACTIONS OF D-MANNOSE AND D-GALACTOSE METHYLHYDRAZONES WITH NITROALKENES [J].

GOMEZGUILLEN, M ;

HANSHANS, F ;

SIMON, JML ;

MARTINZAMORA, ME .

CARBOHYDRATE RESEARCH, 1989, 189 :349-358

← 1 2 3 4 →