Influence of Lewis acids on the Diels–Alder reaction. Part I. An improved synthesis of 7-azanorbornadiene, 3-azaquadricyclane, and azepine derivatives
1969 ◽
Vol 47
(13)
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pp. 2391-2394
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Keyword(s):
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.
1964 ◽
Vol 0
(0)
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pp. 682-688
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1967 ◽
Vol 45
(23)
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pp. 2969-2978
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1978 ◽
Vol 51
(3)
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pp. 132-139
1973 ◽
Vol 51
(24)
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pp. 4125-4136
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Keyword(s):
1990 ◽
Vol 38
(7)
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pp. 1832-1835
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1978 ◽
Vol 43
(19)
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pp. 3727-3729
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1971 ◽
Vol 49
(19)
◽
pp. 3152-3157
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Keyword(s):