PREPARATION OF ORTHO-HYDROXYALKYLANILINES AS ORTHO-QUINONE METHIDE IMINE PRECURSORS VIA AN AMINOBORANE COMPLEX

被引：28

作者：

MIGNEAULT, D ^{[1
]}

BERNSTEIN, MA ^{[1
]}

LAU, CK ^{[1
]}

机构：

[1] MERCK FROSST CANADA INC,MERCK FROSST CTR THERAPEUT RES,DEPT MED CHEM,POINTE CLAIRE,PQ H9R 4P8,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1995年 / 73卷 / 09期

关键词：

QUINONE METHIDE IMINE; ORTHO-HYDROXYALKYLANILINE; AZACANNABINOIDS;

D O I：

10.1139/v95-186

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general process for ortho-specific hydroxyalkylation of secondary anilines has been developed. N-Methylanilinochlorophenylboranes react readily with aryl aldehydes, and with alpha,beta-unsaturated or saturated aliphatic aldehydes to give the corresponding ortho-hydroxyalkylanilines in good yield. Thermolysis of the latter generated the corresponding ortho-quinone methide imine, which can participate in an electrocyclic or intramolecular [4+2] cycloaddition reaction to give various dihydro- and tetrahydroquinoline derivatives. Application of the method to the syntheses of 5-aza analogs of hexahydrocannabinol is demonstrated.

引用

页码：1506 / 1513

页数：8

共 14 条

[1] N-PHENYLBENZOAZETINE [J].