title: Interrupted imino-Nazarov cyclization of 1-aminopentadienyl cation and related cascade process.
abstract: 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.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore).
authors.forename: Ronny
authors.initials: R
authors.lastname: William
authors.forename: Siming
authors.initials: S
authors.lastname: Wang
authors.forename: Feiqing
authors.initials: F
authors.lastname: Ding
authors.forename: Elise Nerissa
authors.initials: EN
authors.lastname: Arviana
authors.forename: Xue-Wei
authors.initials: XW
authors.lastname: Liu
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D002412:Cations / Q000737:chemistry; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D002412:Cations; D003517:Cyclopentanes; D007211:Indoles; D058116:Lewis Acids; D011804:Quinolines; D012834:Silver; C057812:indoline; C542964:1,2,3,4-tetrahydroquinoline; C013905:cyclopentenone
keywords: cations; cyclizations; electrocyclization; rearrangement; synthetic methods