Regioselective synthesis of 1,3,5-substituted pyrazoles from acetylenic ketones and hydrazines

被引：133

作者：

Bishop, BC ^{[1
]}

Brands, KMJ ^{[1
]}

Gibb, AD ^{[1
]}

Kennedy, DJ ^{[1
]}

机构：

[1] Merck Sharp & Dohme Res Labs, Dept Proc Res, Hoddesdon EN11 9BU, Herts, England

来源：

SYNTHESIS-STUTTGART | 2004年 / 01期

关键词：

pyrazoles; ketones; alkynes; hydrazones; regioselectivity;

D O I：

10.1055/s-2003-44376

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of diversely substituted 1,3,5-substituted pyrazoles from the reaction of acetylenic ketones with substituted hydrazines is reported. The reactions were shown to be highly regioselective regardless of the nature of the substituents in the substrates and afforded essentially single pyrazole isomers in excellent yields.

引用

页码：43 / 52

页数：10

共 27 条

[1] Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia
Ahmed, MSM
Mori, A
[J]. ORGANIC LETTERS, 2003, 5 (17) : 3057 - 3060
[2] REGIOSPECIFIC SYNTHESIS OF 1-ARYLPYRAZOLES
ALBEROLA, A
ANDRES, C
ORTEGA, AG
PEDROSA, R
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (05) : 1575 - 1576
[3] ALFARKH YA, 1978, CHEM PHARM BULL, V26, P1298
[4] NONPEPTIDE ANGIOTENSIN-II ANTAGONISTS DERIVED FROM 1H-PYRAZOLE-5-CARBOXYLATES AND 4-ARYL-1H-IMIDAZOLE-5-CARBOXYLATES
ASHTON, WT
HUTCHINS, SM
GREENLEE, WJ
DOSS, GA
CHANG, RSL
LOTTI, VJ
FAUST, KA
CHEN, TB
ZINGARO, GJ
KIVLIGHN, SD
SIEGL, PKS
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (23) : 3595 - 3605
[5] 4-3(5)-PYRAZOLYLPYRIDINIUM SALTS - A NEW CLASS OF HYPOGLYCEMIC AGENTS
BAUER, VJ
DALALIAN, HP
FANSHAWE, WJ
SAFIR, SR
TOCUS, EC
BOSHART, CR
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (05) : 981 - &
[6] Reaction between hydrazines and chiral α-acetylenic ketones:: synthesis of novel enantiomerically pure pyrazolyl-β-amino alcohols
Cabarrocas, G
Ventura, M
Maestro, M
Mahía, J
Villalgordo, JM
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (12) : 2483 - 2493
[7] Studies on copper(I) catalysed cross-coupling reactions:: A convenient and facile method for the synthesis of diversely substituted α,β-acetylenic ketones
Chowdhury, C
Kundu, NG
[J]. TETRAHEDRON, 1999, 55 (22) : 7011 - 7016
[8] Propargyladehyds and the phenylpropargyaldehyds
Claisen, L
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1903, 36 : 3664 - 3673
[9] COISPEAU G, 1970, B SOC CHIM FR, P689
[10] COISPEAU G, 1970, B SOC CHIM FR, P2717

← 1 2 3 →