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Mitt. XV: Struktur und reaktivität von isoanellierten heterocyclischen systemen mit 4nπ‐ und (4n + 2) π‐elektronen . 2‐ t ‐butyl‐4‐methyl‐2,4‐dihydropyrrolo[3,4‐ b ]indole. reaktionen mit aktivierten CC‐dienophilen
Author(s) -
Dyker Gerald,
Kreher Richard P.
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260411
Subject(s) - chemistry , medicinal chemistry , indole test , nucleophile , reagent , ring (chemistry) , reactivity (psychology) , acetal , stereochemistry , organic chemistry , catalysis , pathology , medicine , alternative medicine
Reactions of 2‐ t ‐butyl‐4‐methyl‐2,4‐dihydropyrrolo[3,4‐ b ]indoles with N ‐aryl‐maleimides have been investigated. The formation of 1:1‐cycloadducts is influenced by substituents at 1,3‐position. The consecutive transformations of these intermediates can be controlled by nucleophilic solvents or reagents. Ring opening reactions occur at the labile N,O ‐acetal group of the cycloadducts followed by eliminaton or addition reactions.