A novel one-step synthesis of 2-substituted 6-azaindoles from 3-amino-4-picoline and carboxylic esters

被引:22
作者
Song, JJ [1 ]
Tan, ZL [1 ]
Gallou, F [1 ]
Xu, JH [1 ]
Yee, NK [1 ]
Senanayake, CH [1 ]
机构
[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA
关键词
D O I
10.1021/jo0506480
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dilithiation of 3-amino-4-picoline (1) was achieved with sec-BuLi at room temperature. Condensation of the resulting dianion (2) with carboxylic esters afforded a wide range of 2-substituted 6-azaindoles in good yields.
引用
收藏
页码:6512 / 6514
页数:3
相关论文
共 33 条
[1]  
ANDERRSON PL, 1986, Patent No. 4751235
[2]  
[Anonymous], [No title captured]
[3]   DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS [J].
BEAK, P ;
SNIECKUS, V .
ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) :306-312
[4]  
CADGAN JIG, 1965, J CHEM SOC, P4831
[5]   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
[6]   REACTIONS OF BETA-(LITHIOMETHYL)AZINES WITH NITRILES AS A ROUTE TO PYRROLOPYRIDINES, PYRROLOQUINOLINES, PYRROLOPYRAZINES, PYRROLOQUINOXALINES AND PYRROLOPYRIMIDINES [J].
DAVIS, ML ;
WAKEFIELD, BJ ;
WARDELL, JA .
TETRAHEDRON, 1992, 48 (05) :939-952
[7]  
DININNO FP, 1994, Patent No. 5532261
[8]   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
[9]   AZAINDOLE ANTHELMINTIC AGENTS [J].
FISHER, MH ;
SCHWARTZKOPF, G ;
HOFF, DR .
JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (11) :1168-+
[10]  
GREENHILL JV, 1984, COMPREHENSIVE HETERO, V4, P497