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Interrupted Imino‐Nazarov Cyclization of 1‐Aminopentadienyl Cation and Related Cascade Process
Author(s) -
William Ronny,
Wang Siming,
Ding Feiqing,
Arviana Elise Nerissa,
Liu XueWei
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405251
Subject(s) - chemistry , conrotatory and disrotatory , intramolecular force , aldehyde , catalysis , lewis acids and bases , aniline , cyclopentanone , combinatorial chemistry , organic chemistry , ring (chemistry)
Facile 4π conrotatory imino‐Nazarov cyclization of a 1‐aminopentadienyl cation generated from condensation an aldehyde and secondary aniline in the presence of a catalytic amount of a Lewis acid has been developed. Silver(I)‐catalyzed intramolecular arene trapping of the resulting cyclic oxyallyl cation leads to formation of tricyclic indoline‐fused cyclopentanone. The use of lanthanide salts allows transformation after the initial trapping to afford tetrahydroquinoline‐fused cyclopentenone in a concise manner.