Intramolecular Diels-Alder reactions of N-alkenyl-2(1H)-pyrazinones:: generation of a novel type of cis-1,7-naphthyridine

被引：15

作者：

Rombouts, FJR ^{[1
]}

De Borggraeve, W ^{[1
]}

Toppet, SM ^{[1
]}

Compernolle, F ^{[1
]}

Hoornaert, GJ ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Organ Synth Lab, B-3001 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(01)01545-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular Diels Alder reaction of three 1-(omega -alkenyl)-2(1H)-pyrazinones was investigated. Cycloaddition was shown to proceed for 1-(4-pentenyl)- and 1-(5-hexenyl)-2(1H)- pyrazinone 5a and 5b to give the corresponding tricyclic hydrolysed adducts 7a and 7b, but not for the 1-(3-butenyl) derivative 5c. In contrast to 7b. the more strained 7a under,,vent selective acidic solvolysis of the tertiary lactam group to give methyl cis-8-oxo-6-phenyldecahydro[1,7]naphthyridine-6-carboxylate 8. An NMR analysis of 8 is presented, (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7397 / 7399

页数：3

共 9 条

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