DIHYDROISOBENZOFURANS AND ISOINDOLINES BY INTRAMOLECULAR INVERSE DIELS-ALDER REACTIONS OF PYRIDINES

被引：3

作者：

BIEDRZYCKI, M ^{[1
]}

DEBIE, DA ^{[1
]}

VANDERPLAS, HC ^{[1
]}

机构：

[1] AGR UNIV WAGENINGEN,ORGAN CHEM LAB,DREIJENPLEIN 8,6703 HB WAGENINGEN,NETHERLANDS

来源：

TETRAHEDRON | 1990年 / 46卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(01)85441-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyridines being substituted at position 2 or 3 with a silylated propynyloxymethyl side-chain undergo a thermolytic intramolecular Diels-Alder reaction with formation of dihydroisobenzofurans. The 3-substituted pyridines are found to be more reactive than the 2-substituted ones. Substitution of both hydrogens in the methylene group at the (α-position of this side-chain by one methyl as well as one phenyl substituent leads to a considerable increase of the reaction rate. In a similar way, from the N-acetyl derivative of 3-trimethylsilyl-propynylaminomethylpyridine, the isoindoline system is formed. The rate of the reaction is considerably lower than that of the corresponding propynyloxymethyl derivative. © 1990.

引用

页码：607 / 614

页数：8

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