132932-77-5Relevant academic research and scientific papers
CYCLOADDITIONS OF PYRANOINDOL-3-ONES WITH 1,2-BIS-ACCEPTOR SUBSTITUTED ETHENES: FIRST EVIDENCE FOR A NON-CONCERTED DIELS-ALDER STEP
Pindur, Ulf,Erfanian-Abdoust, Houshang
, p. 1751 - 1761 (1990)
The Diels-Alder reactions of pyranoindol-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 cycloaddition is mainly in operation.The pyridoindol-3-one (11) was attacked by dienophiles only at the lactam nitrogen atom and cycloaddition did not take place.
