A general and efficient synthesis of azaindoles and diazaindoles

被引：43

作者：

Harcken, C ^{[1
]}

Ward, Y ^{[1
]}

Thomson, D ^{[1
]}

Riether, D ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Med Chem, Ridgefield, CT 06877 USA

来源：

SYNLETT | 2005年 / 20期

关键词：

azaindole; diazaindoles; cyclization; heterocycles; alkynes;

D O I：

10.1055/s-2005-922753

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The DBU-mediated cyclization of ortho-(Boc-amino)alkynyl pyridines, -pyridazines, -pyrimidines and -pyrazines efficiently generates azaindoles and diazaindoles, respectively. The reaction proceeds under mild conditions and in high yields. A variety of functional groups are tolerated.

引用

页码：3121 / 3125

页数：5

共 23 条

[1] SOME REACTIONS OF 3-HALOGENOCINNOLINES CATALYZED BY PALLADIUM COMPOUNDS [J].

AMES, DE ;

BULL, D .

TETRAHEDRON, 1982, 38 (03) :383-387

[2] ALKYNYL-QUINOXALINES AND DIALKYNYL-QUINOXALINES - SYNTHESIS OF CONDENSED QUINOXALINES [J].

AMES, DE ;

BROHI, MI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (07) :1384-1389

[3]

Brière JF, 2000, HETEROCYCLES, V52, P1371

[4] 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

[5]

Crous R, 1999, HETEROCYCLES, V51, P721

[6] METALATION SRN1 COUPLING IN HETEROCYCLIC SYNTHESIS - A CONVENIENT METHODOLOGY FOR RING FUNCTIONALIZATION [J].

ESTEL, L ;

MARSAIS, F ;

QUEGUINER, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2740-2744

[7]

Hands D, 1996, SYNTHESIS-STUTTGART, P877

[8] DIRECTED LITHIATION OF 3-[(TERT-BUTOXYCARBONYL) AMINO]-2-METHOXYPYRIDINES - SYNTHETIC ROUTE TO NEVIRAPINE AND ITS 4-SUBSTITUTED DERIVATIVES [J].

KELLY, TA ;

PATEL, UR .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1875-1877

[9] Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases [J].

Koradin, C ;

Dohle, W ;

Rodriguez, AL ;

Schmid, B ;

Knochel, P .

TETRAHEDRON, 2003, 59 (09) :1571-1587

[10] SYNTHESIS OF 7-AZAINDOLE AND 7-AZAOXINDOLE DERIVATIVES THROUGH A PALLADIUM-CATALYZED CROSS-COUPLING REACTION [J].

KUMAR, V ;

DORITY, JA ;

BACON, ER ;

SINGH, B ;

LESHER, GY .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6995-6998

← 1 2 3 →