CONSTRUCTION OF POLYCYCLIC COMPOUNDS BY CYCLOCARBONYLATION .6. PALLADIUM-CATALYZED CYCLOCARBONYLATION OF 3-(HETEROARYL)ALLYL ACETATES

被引：60

作者：

IWASAKI, M ^{[1
]}

KOBAYASHI, Y ^{[1
]}

LI, JP ^{[1
]}

MATSUZAKA, H ^{[1
]}

ISHII, Y ^{[1
]}

HIDAI, M ^{[1
]}

机构：

[1] UNIV TOKYO,FAC ENGN,DEPT SYNTHET CHEM,BUNKYO KU,TOKYO 113,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 05期

关键词：

D O I：

10.1021/jo00005a046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130-170-degrees-C under 50-70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively. The synthetic utility of the reaction was demonstrated by the synthesis of cannabifuran from isothymol.

引用

页码：1922 / 1927

页数：6

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