INTRAMOLECULAR DIELS-ALDER REACTIONS .4. ADDITIONS TO NAPHTHALENE

被引：6

作者：

CIGANEK, E ^{[1
]}

WUONOLA, MA ^{[1
]}

HARLOW, RL ^{[1
]}

机构：

[1] DUPONT CO INC,CENT RES & DEV,EXPTL STN,WILMINGTON,DE 19880

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1994年 / 31卷 / 05期

关键词：

D O I：

10.1002/jhet.5570310523

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Methyl-N-2-propynyl-1-naphthalenecarboxamide, N-methyl-N-2-propynyl-1-naphthaleneacetamide, and N-methyl-N-3-butynyl-1-naphthalenecarboxamide undergo intramolecular Diels-Alder reactions at 190-degrees, 250-degrees, and 270-degrees to give lactams 1, 6, and 9, respectively. The cyclization temperatures are higher by 80-120-degrees as compared to those of the corresponding anthracene derivatives. Elaboration of lactam 6 gave the trans-4a-aryldecahydroisoquinoline derivative 7a which, as the (-) isomer, was shown to have the same absolute stereochemistry as morphine.

引用

页码：1251 / 1257

页数：7

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