Highly regioselective synthesis of 1-aryl-3,4,5-substituted pyrazoles

被引：112

作者：

Gosselin, Francis

O'Shea, Paul D.

Webster, Robert A.

Reamer, Robert A.

Tillyer, Richard D.

Grabowski, Edward J. J.

机构：

[1] Merck Frosst Ctr Therapeut Res, Dept Proc Res, Kirkland, PQ H9H 3L1, Canada

[2] Merck & Co Inc, Merck Sharp & Dohme Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

SYNLETT | 2006年 / 19期

关键词：

1,3-diketones; arylhydrazines; cyclocondensation; regioselectivity; amide solvents;

D O I：

10.1055/s-2006-956487

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly regioselective synthesis of 1-aryl-3,4,5-substituted pyrazoles based on the condensation of 1,3-diketones with arylhydrazines is described. The reaction proceeds at room temperature in N,N-dimethylacetamide and furnishes pyrazoles in 59-98% yields.

引用

收藏

页码：3267 / 3270

页数：4

相关论文

共 21 条

[1]

DEAN JA, 1985, LANGES HDB CHEM, P103

[2] 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

[3]

Elguero J., 1997, COMPREHENSIVE HETERO, V5, P167, DOI DOI 10.1016/B978-008096519-2.00072-2

[4]

[5]

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

[6]

GILCHRIST TL, 1992, HETEROCYCLIC CHEM, P294

[7] Parallel synthesis of potent, pyrazole-based inhibitors of Helicobacter pylori dihydroorotate dehydrogenase [J].

Haque, TS ;

Tadesse, S ;

Marcinkeviciene, J ;

Rogers, MJ ;

Sizemore, C ;

Kopcho, LM ;

Amsler, K ;

Ecret, LD ;

Zhan, DL ;

Hobbs, F ;

Slee, A ;

Trainor, GL ;

Stern, AM ;

Copeland, RA ;

Combs, AP .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (21) :4669-4678

[8] Regioselective synthesis of 1,3,5-triaryl-4-alkylpyrazoles: Novel ligands for the estrogen receptor [J].

Huang, YR ;

Katzenellenbogen, JA .

ORGANIC LETTERS, 2000, 2 (18) :2833-2836

[9] Regioselective synthesis of polysubstituted pyrazoles and isoxazoles [J].

Katritzky, AR ;

Wang, MY ;

Zhang, SM ;

Vonkov, AVV ;

Steel, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6787-6791

[10] Sequential functionalization of pyrazole 1-oxides via regioselective metalation: Synthesis of 3,4,5-trisubstituted 1-hydroxypyrazoles [J].

Paulson, AS ;

Eskildsen, J ;

Vedso, P ;

Begtrup, M .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3904-3907