CONDENSATION OF REISSERT HYDROFLUOROBORATE SALTS WITH ALKENES AND ALKYNES

被引：32

作者：

MCEWEN, WE ^{[1
]}

CABELLO, CC ^{[1
]}

CALABRO, MA ^{[1
]}

ORTEGA, AM ^{[1
]}

STOTT, PE ^{[1
]}

ZAPATA, AJ ^{[1
]}

ZEPP, CM ^{[1
]}

LUBINKOWSKI, JJ ^{[1
]}

机构：

[1] UNIV SIMON BOLIVAR, DEPT CHEM, CARACAS 108, VENEZUELA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1978年 / 44卷 / 01期

关键词：

D O I：

10.1021/jo01315a025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydrofluoroborate salts of 2-acyl-1, 2-dihydroisoquinaldonitriles (Reissert compounds) undergo reactions with alkenes to give substituted 2-(1-isoquinolyl)pyrroles and with alkynes to give substituted pyrrolo[2, 1-a]isoqui-nolines. To expand the scope and synthetic usefulness of these reactions, a wide variety of Reissert salts, alkenes, and alkynes, respectively, have been utilized. The reactions are general in nature. They take place successfully when the acyl group of the Reissert compound is varied from a simple aliphatic one (N-acetyl, for example) to a sterically hindered aromatic one [N-(1-naphthoyl)]. The olefin reactions take place with monosubstituted ethylenes (styrene) and with 1, 2-disubstituted ethylenes (trcms-stilbene). Also, the reactions occur when either electron-withdrawing (as in diethyl maleate) or electron-donating [as in 1-(3, 4-dimethoxyphenyl)propene] substituents are bonded to the ethylene moiety. With regard to the alkyne reactions, wide variations in either the Reissert salt or the alkynes are also consonant with successful reactions. © 1979, American Chemical Society. All rights reserved.

引用

页码：111 / 117

页数：7

共 19 条

[1]

BIRCH AJ, 1972, TETRAHEDRON LETT, P4789

[2] Aluminium oxide with gradual absorption capacity to chromatographic absorption. [J].