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

页码：5204 / 5211

页数：8

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