Influence of Lewis acids on the Diels–Alder reaction. Part I. An improved synthesis of 7-azanorbornadiene, 3-azaquadricyclane, and azepine derivatives
- 1 July 1969
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 47 (13) , 2391-2394
- https://doi.org/10.1139/v69-390
Abstract
Depending on the experimental conditions the AlCl3-promoted reaction of 1-carbomethoxypyrrole and dimethyl acetylenedicarboxylate yields 2,3,7-tricarbomethoxy-7-azanorbornadiene, either in almost quantitative yield or together with dimethyl 1-carbomethoxy-2-pyrrolyl maleate and fumarate. The azanorbornadiene has been quantitatively converted to 1,4,5-tricarbomethoxyazepine via the corresponding 3-azaquadricyclane. The proton magnetic resonance spectra were analyzed with the aid of the Laocoon II program.Keywords
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