Palladium-catalyzed C-N bond formation:: synthesis of 1-aryl-1H-pyrazoles from β-bromovinyl aldehydes and arylhydrazines

被引：47

作者：

Cho, Chan Sik ^{[1
]}

Patel, Daksha B.

机构：

[1] Kyungpook Natl Univ, Ind Technol Res Inst, Taegu 702701, South Korea

[2] Kyungpook Natl Univ, Dept Appl Chem, Taegu 702701, South Korea

来源：

TETRAHEDRON | 2006年 / 62卷 / 26期

关键词：

beta-bromovinyl aldehydes; C-N bond formation; arylhydrazines; palladium catalyst; pyrazoles;

D O I：

10.1016/j.tet.2006.04.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic and acyclic beta-bromovinyl aldehydes are cyclized with an array of arylhydrazines in toluene at 125 degrees C in the presence of a palladium catalyst and a phosphorus chelating ligand together with (NaOBu)-Bu-t to give 1-aryl-1H-pyrazoles in moderate to good yields. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6388 / 6391

页数：4

共 36 条

[1]

[Anonymous], ANGEW CHEM INT ED

[2] Catalytic amination of 2-substituted pyridines with hydrazine derivatives [J].

Arterburn, JB ;

Rao, KV ;

Ramdas, R ;

Dible, BR .

ORGANIC LETTERS, 2001, 3 (09) :1351-1354

[3] Synthesis of quinolines via ruthenium-catalysed amine exchange reaction between anilines and trialkylamines [J].

Cho, CS ;

Oh, BH ;

Kim, JS ;

Kim, TJ ;

Shim, SC .

CHEMICAL COMMUNICATIONS, 2000, (19) :1885-1886

[4] Palladium-catalyzed Sonogashira coupling reaction followed by isomerization and cyclization [J].

Cho, CS .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (17) :4094-4097

[5] Palladium-catalyzed aromatization of β-bromovinyl aldehydes with alkenes [J].

Cho, CS ;

Patel, DB ;

Shim, SC .

TETRAHEDRON, 2005, 61 (40) :9490-9494

[6] A palladium-catalyzed route for α-alkylation of ketones by primary alcohols [J].

Cho, CS .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 240 (1-2) :55-60

[7] An efficient dealkylative addition of trialkylamines to dialkyl acetylenedicarboxylates in the presence of a metallic chloride [J].

Cho, CS .

TETRAHEDRON LETTERS, 2005, 46 (09) :1415-1417

[8] Palladium-catalyzed tandem Heck and aldol reactions between 2-bromobenzaldehydes and functionalized alkenes leading to naphthalenes [J].

Cho, CS ;

Lim, DK ;

Zhang, JQ ;

Kim, TJ ;

Shim, SC .

TETRAHEDRON LETTERS, 2004, 45 (29) :5653-5656

[9] Facile palladium-catalysed synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines [J].

Cho, CS ;

Lim, DK ;

Heo, NH ;

Kim, TJ ;

Shim, SC .

CHEMICAL COMMUNICATIONS, 2004, (01) :104-105

[10] Ruthenium-catalyzed regioselective synthesis of 2-substituted indoles via ring-opening of epoxides by anilines [J].

Cho, CS ;

Kim, JH ;

Choi, HJ ;

Kim, TJ ;

Shim, SC .

TETRAHEDRON LETTERS, 2003, 44 (14) :2975-2977

← 1 2 3 4 →