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Intramolecular Pauson-Khand Reaction of Alkyne-Ketenimines and Related [4+2] and [2+2] Cycloadditions

[ Vol. 15 , Issue. 5 ]

Author(s):

Mateo Alajarin*, Francisco-Jose Ballester and Angel Vidal*   Pages 418 - 424 ( 7 )

Abstract:


The first examples of intramolecular Pauson-Khand reactions involving ketenimines are reported. The alkyne-ketenimines participate through the C=C bond of the ketenimine fragment in the [2+2+1] cyclization process giving rise to cyclopenta[b]quinolin-2-ones. In the absence of metal carbonyl complexes, two competitive periselective cycloadditions occur when the alkyne-ketenimines are heated in benzene solution: a [4+2] process leading to benz[b]acridines as the major products, and a [2+2] route giving minor amounts of cyclobuta[b]quinolines.

Keywords:

Alkyne, ketenimine, carbon monoxide, Pauson-khand, intramolecular, [4+2] cycloaddition, [2+2] cycloaddition, heterocycles.

Affiliation:

Departamento de Quimica Organica, Facultad de Quimica, Universidad de Murcia, Regional Campus of International Excellence "Campus Mare Nostrum", Espinardo, 30100 Murcia, Departamento de Quimica Organica, Facultad de Quimica, Universidad de Murcia, Regional Campus of International Excellence "Campus Mare Nostrum", Espinardo, 30100 Murcia, Departamento de Quimica Organica, Facultad de Quimica, Universidad de Murcia, Regional Campus of International Excellence "Campus Mare Nostrum", Espinardo, 30100 Murcia

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