Palladium-Catalyzed Synthesis of 2,3-Disubstituted 5-Azaindoles via Heteroannulation Reaction and of 2-Substituted 5-Azaindoles through Domino Sila-Sonogashira/5-Endo Cyclization

被引：26

作者：

Livecchi, Marion ^{[1
,2
,3
]}

Calvet, Geraldine ^{[1
,2
]}

Schmidt, Frederic ^{[1
,2
]}

机构：

[1] Inst Curie, Ctr Rech, F-75248 Paris, France

[2] CNRS, UMR 176, F-75248 Paris, France

[3] Univ Paris 05, Ecole Doctorale MTCE, F-75006 Paris, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 11期

关键词：

HETEROCYCLES; INDOLES; AZAINDOLE; FUNCTIONALIZATION; 4-AZAINDOLES; DERIVATIVES; INHIBITORS;

D O I：

10.1021/jo300481s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and efficient procedure for the synthesis of 2,3-disubstituted 5-azaindoles through the palladium-catalyzed heteroannulation of 4-acetamido-3-iodopyridines and diaryl-, dialkyl-, or arylalkylalkynes is described along with a study of the reaction regioselectivity. The preparation of 2-monosubstituted 5-azaindoles via sila-Sonogashira/5-endo cyclization is also reported. These methods allowed us to prepare 36 diversely substituted 5-azaindoles in good yields.

引用

页码：5006 / 5016

页数：11

共 55 条

[1]

Bartoli G., 1978, J CHEM SOC P1, V7, P692

[2]

Batcho A.D., 1985, Org. Synth, V63, P214, DOI DOI 10.15227/orgsyn.063.0214

[3]

Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671

[4]

Bemotas R. C., 2009, BIOORG MED CHEM LETT, V19, P6935

[5] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[6] 2-Aryl and 2-heteroaryl pyrrolo[2,3-b]quinoxalines via copper-catalyzed reaction of 1-alkynes with 2-bromo-3-trifluoroacetamidoquinoxaline [J].

Cacchi, S ;

Fabrizi, G ;

Parisi, LM ;

Bernini, R .

SYNLETT, 2004, (02) :287-290

[7] Nitrogen-containing heterocycles via palladium-catalyzed reaction of alkynes with organic halides or triflates [J].

Cacchi, S ;

Fabrizi, G ;

Parisi, LM .

HETEROCYCLES, 2002, 58 :667-682

[8] Synthesis of Polysubstituted 5-Azaindoles via Palladium-Catalyzed Heteroannulation of Diarylalkynes [J].

Calvet, Geraldine ;

Livecchi, Marion ;

Schmidt, Frederic .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (11) :4734-4740

[9] Discovery of an orally efficacious inhibitor of coagulation factor Xa which incorporates a neutral P1 ligand [J].

Choi-Sledeski, YM ;

Kearney, R ;

Poli, G ;

Pauls, H ;

Gardner, C ;

Gong, Y ;

Becker, M ;

Davis, R ;

Spada, A ;

Liang, G ;

Chu, V ;

Brown, K ;

Collussi, D ;

Leadley, R ;

Rebello, S ;

Moxey, P ;

Morgan, S ;

Bentley, R ;

Kasiewski, C ;

Maignan, S ;

Guilloteau, JP ;

Mikol, V .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (05) :681-684

[10]

Fischer E., 1883, CHEM BER-RECL, V16, P2241, DOI [10.1002/cber.188301602141, DOI 10.1002/CBER.188301602141]

← 1 2 3 4 5 6 →