Synthesis of novel benzo[h][1,6]naphthyridine derivatives from 4-aminoquinoline and cyclic β-ketoester

被引：13
|
作者：
Toche, Raghunath B. [1 ]
Pagar, Balasaheb P. [1 ]
Zoman, Ravindra R. [1 ]
Shinde, Goraksha B. [1 ]
Jachak, Madhukar N. [1 ]
机构：
[1] BH Commerce & AM Sci Coll, KRT Arts, Dept Chem, Organ Chem Res Ctr, Nasik 422002, Maharashtra, India
来源：
TETRAHEDRON | 2010年 / 66卷 / 27-28期
关键词：
alpha-Acetyl gamma-butyrolactone; Benzo[h][1,6]naphthyridine; 2,8-Dichloroquinolin-4-amine; Regioselective; 5-HT4; RECEPTORS; AGENTS; AMINES;
D O I：
10.1016/j.tet.2010.04.085
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This paper describes the synthesis of 2,8-dichloroquinolin-4-amine 4 and 4,5,7-trichloro-3-(2-chloroethyl)-2-methylbenzo[h][1,6]naphthyridine 8 as novel class of building blocks. Also describes the regioselective S(N)Ar reactions of 2,4,8-trichloroquinoline 2 on C(2) and C(4) positions with azide, similarly S(N)Ar reactions of benzo[h][1,6]naphthyridine 8 at C(4), C(5) positions, and S(N)2 reactions on C(3)-(2-chloroethyl) side chain with nucleophiles such as primary aromatic amines, methoxide/ethoxide, and azide at different temperatures. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5204 / 5211
页数：8
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