Heterocycles p. 1751 - 1761 (1990)
Update date:2022-08-05
Topics:
Pindur, Ulf
Erfanian-Abdoust, Houshang
The Diels-Alder reactions of pyrano<3,4-b>indol-3-ones (1) with 1,2-bis-acceptor substituted ethenes yield stable 1,2-dihydrocarbazoles and fully aromatized carbazoles.The results of stereochemical determinations in the 1,2-dihydrocarbazoles and, in one case, the occurrence of a bimolecular, diene-catalyzed dienophile isomerization provide the first evidence that a non-concerted <4 + 2>cycloaddition is mainly in operation.The pyrido<3,4-b>indol-3-one (11) was attacked by dienophiles only at the lactam nitrogen atom and cycloaddition did not take place.
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Doi:10.1002/jhet.5570270746
(1990)Doi:10.1039/c3ra41935e
(2013)Doi:10.1021/acs.joc.7b03033
(2018)Doi:10.1021/ol402125t
(2013)Doi:10.1021/jo00052a066
(1992)Doi:10.1002/jhet.999
(2013)