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

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

Volume: 15 Issue: 5

Author(s): Mateo Alajarin*, Francisco-Jose Ballester and Angel Vidal*

Affiliation:

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

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

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

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.

Cite this article as:

Alajarin Mateo *, Ballester Francisco-Jose and Vidal Angel *, Intramolecular Pauson-Khand Reaction of Alkyne-Ketenimines and Related [4+2] and [2+2] Cycloadditions, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178615666171220142731