Synthesis and some properties of alkynyl derivatives of 1,3-dialkylperimidones. An example of the 1,2-palladium migration in the Sonogashira reaction

A series of mono-, di-, tri- and tetra-alkynyl derivatives of 1,3-dimethyl- and 1,3-diethyl-1H-perimidine-2(3H)-ones have been obtained from the corresponding bromides via the Sonogashira reaction. It was found that placing two trimethylsilylethynyl groups into positions 6 and 7 (peri) of the perimi...

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Bibliographic Details
Published in:Tetrahedron 2016-03, Vol.72 (12), p.1547-1557
Main Authors: Filatova, Ekaterina A., Gulevskaya, Anna V., Pozharskii, Alexander F., Ozeryanskii, Valery A.
Format: Article
Language:English
Subjects:
1,2-Palladium migration
1,3-Dialkyl-1H-perimidine-2(3H)-ones
3,5-Diazadibenzo[cd,k]fluoranthenes
Alkynes
Deformation
Derivatives
Formations
Heterocyclic compounds
Migration
Naphthalene
Sonogashira coupling
Synthesis
Tetrahedrons
Thermal peri-cyclizations
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Summary:A series of mono-, di-, tri- and tetra-alkynyl derivatives of 1,3-dimethyl- and 1,3-diethyl-1H-perimidine-2(3H)-ones have been obtained from the corresponding bromides via the Sonogashira reaction. It was found that placing two trimethylsilylethynyl groups into positions 6 and 7 (peri) of the perimidone makes a sterically hindered system and, sometimes, is accompanied by a previously unknown 1,2-migration of the Pd(II)-X group in the intermediate complex. Several peri-dialkynyl perimidones were tested for thermal or electrophile-initiated cyclizations resulting in the formation of some new polynuclear heterocyclic compounds, mostly derivatives of 3,5-diazadibenzo[cd,k]fluoranthene. The cyclizations have been found to proceed with more difficulty than those of 1,8-bis(phenylethynyl)naphthalene. This fact was ascribed to larger in-plane deformation of the naphthalene moiety in the perimidones that results in moving the peri-alkynyl groups apart from each other. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.02.003