AN IMPROVED SYNTHESIS OF 2,2-DISUBSTITUTED-1,2-DIHYDROQUINOLINES AND THEIR CONVERSION TO 3-CHLORO-2,2-DISUBSTITUTED-TETRAHYDROQUINOLINES

被引：71

作者：

WILLIAMSON, NM ^{[1
]}

MARCH, DR ^{[1
]}

WARD, AD ^{[1
]}

机构：

[1] UNIV ADELAIDE,DEPT CHEM,ADELAIDE,SA 5005,AUSTRALIA

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 42期

关键词：

D O I：

10.1016/0040-4039(95)01572-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(1,1-disubstitutedpropargyl)anilines can be cyclised to 2,2-disubstituted-12-dihydroquinolines by refluxing them in toluene containing cuprous chloride. Electron donating groups in the para position of the ring enhance the reaction rare and electron withdrawing groups markedly decrease the rare. The derived N-acetyldihydroquinolines can be cis dichlorinated and selectively monodechlorinated at the benzylic position to produce 3-chlorotetrahydroquinolines.

引用

页码：7721 / 7724

页数：4

共 9 条

[1]

EASTON NR, 1962, J ORG CHEM, V27, P4713

[2]

EASTON NR, 1967, Patent No. 3331846

[3] THE ALKYLATION OF AMINES WITH T-ACETYLENIC CHLORIDES - PREPARATION OF STERICALLY HINDERED AMINES [J].