REACTIONS OF 2-PHENYL-4H-1,3,2-BENZODIOXABORIN, A STABLE ORTHO-QUINONE METHIDE PRECURSOR

被引：57

作者：

CHAMBERS, JD ^{[1
]}

CRAWFORD, J ^{[1
]}

WILLIAMS, HWR ^{[1
]}

DUFRESNE, C ^{[1
]}

SCHEIGETZ, J ^{[1
]}

BERNSTEIN, MA ^{[1
]}

LAU, CK ^{[1
]}

机构：

[1] MERCK FROSST CTR THERAPEUT RES,DEPT MED CHEM,POB 1005,POINTE CLAIRE H9R 4P8,QUEBEC,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1992年 / 70卷 / 06期

关键词：

D O I：

10.1139/v92-216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thermolysis of 1-phenyl-4H-1,3,2-benzodioxaborins generated the corresponding ortho-quinone methides, which were found to undergo intermolecular cycloaddition reactions with ethyl vinyl ether, dihydropyran, beta-methylstyrene, cyclohexene, and 1-ethoxy-1-z-trimethylsiloxy-1-propenes to give various substituted chromans. Intramolecular trapping of the quinone methides with an olefin led to the syntheses of several analogs of tetrahydrocannabinols. ortho-Quinone methides, generated by treatment of the 2-phenyl-4H-1,3,2-benzodioxaborins with a Lewis acid, react with various nucleophiles to give the corresponding 1,4-addition products. Thus, alkyl and aryl thiols, alcohols, amine, hydride, allyl trimethylsilane, acetophenone, and diethylmalonate as well as some aryl compounds react with the quinone methide to give various 2-substituted phenols. Intramolecular reaction of the quinone methide with an aryl group led to the preparation of some 4-phenylchromans and tetralins.

引用

页码：1717 / 1732

页数：16