Regioselective rapid analogue syntheses of 1-methyl-3,5-diarylpyrazoles via palladium-catalysed coupling to 3(5)-pyrazolyl nonaflates

被引：29

作者：

Bourrain, S ^{[1
]}

Ridgill, M ^{[1
]}

Collins, I ^{[1
]}

机构：

[1] Merck Sharp & Dohme Res Labs, Neurosci Res Ctr, Dept Med Chem, Harlow CM20 2QR, Essex, England

来源：

SYNLETT | 2004年 / 05期

关键词：

regioselectivity; chemoselectivity; palladium; cross-coupling; heterocycles;

D O I：

10.1055/s-2004-820020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective rapid analogue syntheses of 1-methyl-3,5-diarylpyrazoles were developed, based on Pd-catalysed couplings to 1-methyl-3(5)-arylpyrazole nonaflates, which offered an advantage in hydrolytic stability over the corresponding triflates. The new bifunctional reagent 1-methyl-3-bromo-pyrazol-5-yl nonaflate underwent highly chemoselective Pd-catalysed couplings to the nonaflate, followed by Suzuki couplings to the bromide, allowing sequential, regioselective introduction of the two aryl substituents.

引用

页码：795 / 798

页数：4

共 28 条

[1]

Balle T, 2002, SYNTHESIS-STUTTGART, P1509

[2] 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

[3]

BOSCHI PM, 1981, Patent No. 4256902

[4]

COATES RM, 1984, SYNTHESIS-STUTTGART, P434

[5] Rapid analogue syntheses of heteroaromatic compounds [J].

Collins, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (17) :2845-2861

[6] Rapid analogue syntheses of heteroaromatic compounds [J].

Collins, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (17) :1921-1940

[7]

Cottineau B, 2002, SYNLETT, P769

[8]

ELGERO J, 1996, COMPERHENSIVE HETERO, V3, P1

[9]

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

[10]

← 1 2 3 →