Synthesis and regioselective alkylation of 1,6-and 1,7-naphthyridines

被引:28
作者
Colandrea, VJ [1 ]
Naylor, EM [1 ]
机构
[1] Merck Res Labs, Dept Med Chem, Rahway, NJ 07065 USA
关键词
D O I
10.1016/S0040-4039(00)01400-3
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
A regioselective alkylation of naphthyridines 4a-d, through the action of ethylchloroformate and benzylstannane 5, afforded the benzyl substituted dihydronaphthyridines 3a-d. These key intermediates 3a-d were transformed into the desired targets 2a-d in seven steps. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8053 / 8057
页数:5
相关论文
共 11 条
[1]
BROCKUNIER L, 1999, Patent No. 44609A
[2]
Discovery of 1,6-naphthyridines as a novel class of potent and selective human cytomegalovirus inhibitors [J].
Chan, L ;
Jin, H ;
Stefanac, T ;
Lavallée, JF ;
Falardeau, G ;
Wang, W ;
Bédard, J ;
May, S ;
Yuen, L .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (16) :3023-3025
[3]
REGIOSELECTIVE SUBSTITUTION IN AROMATIC 6-MEMBERED NITROGEN-HETEROCYCLES [J].
COMINS, DL ;
OCONNOR, S .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1988, 44 :199-267
[4]
A facile preparation of benzyltrimethylstannanes and their utility in the synthesis of 1-benzyl-1,2-dihydroisoquinolines [J].
Deline, JE ;
Miller, RB .
TETRAHEDRON LETTERS, 1998, 39 (13) :1721-1724
[5]
A NEW APPROACH TO THE PREPARATION OF 1,6-NAPHTHYRIDINE AND 1,7-NAPHTHYRIDINES [J].
GIAM, CS ;
AMBROZICH, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (05) :265-266
[6]
PALLADIUM(O)-CATALYZED CROSS-COUPLING REACTION OF ALKOXYDIBORON WITH HALOARENES - A DIRECT PROCEDURE FOR ARYLBORONIC ESTERS [J].
ISHIYAMA, T ;
MURATA, M ;
MIYAURA, N .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7508-7510
[7]
KRESS TJ, 1967, J CHEM SOC CHEM COMM, P3
[8]
3-pyridylethanolamines:: Potent and selective human β3 adrenergic receptor agonists [J].
Naylor, EM ;
Colandrea, VJ ;
Candelore, MR ;
Cascieri, MA ;
Colwell, LF ;
Deng, LP ;
Feeney, WP ;
Forrest, MJ ;
Hom, GJ ;
MacIntyre, DE ;
Strader, CD ;
Tota, L ;
Wang, PR ;
Wyvratt, MJ ;
Fisher, MH ;
Weber, AE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (21) :3087-3092
[9]
Numata A, 1999, SYNTHESIS-STUTTGART, P306
[10]
ELECTROORGANIC CHEMISTRY .79. EFFICIENT SYNTHESIS OF PYRROLIZIDINE AND INDOLIZIDINE ALKALOIDS UTILIZING ANODICALLY PREPARED ALPHA-METHOXY CARBAMATES AS KEY INTERMEDIATES [J].
SHONO, T ;
MATSUMURA, Y ;
UCHIDA, K ;
TSUBATA, K ;
MAKINO, A .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) :300-304