Abstract
The title compound, C20H23NO2, was obtained via the reaction of N-allyl-N-phenyl-acryl-amide with 3-iodo-cyclo-hex-2-en-1-one using PdCl2(PPh3)2 as a catalyst. The compound crystallizes in the monoclinic space group P21/c. The fused-ring system is not planar and the five- and six-membered rings are trans-fused. The mol-ecular geometry is partially stabilized by an intra-molecular C-H⋯O hydrogen bond, forming an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯π inter-actions into a three-dimensional network. To further analyse the inter-molecular inter-actions, a Hirshfeld surface analysis was performed. The results indicate that the most important contributions to the overall surface are from H⋯H (65.5%), O⋯H/H⋯O (17.5%) and C⋯H/H⋯C (14.3%) inter-actions.
Highlights
The title compound, C20H23NO2, was obtained via the reaction of N-allyl-Nphenylacrylamide with 3-iodocyclohex-2-en-1-one using PdCl2(PPh3)2 as a catalyst
The molecular geometry is partially stabilized by an intramolecular C— HÁ Á ÁO hydrogen bond, forming an S(6) ring motif
The results indicate that the most important contributions to the overall surface are from HÁ Á ÁH (65.5%), OÁ Á ÁH/HÁ Á ÁO (17.5%) and CÁ Á ÁH/HÁ Á ÁC (14.3%) interactions
Summary
A cascade reaction is a chemical process that comprises at least two consecutive reactions such that each subsequent reaction occurs only by virtue of the chemical functionality formed in the previous step (Nicolaou et al, 2010; Jash et al, 2019; Knowles et al, 2021). McGlacken described a Pd-catalysed coupling procedure for tricyclic oxoisochromene derivatives, which represents an example of the arylation of activated carbocyclic enone-based substrates (Muimhneachain et al, 2017). Huang and co-workers have realized a series of reactions including Sonogashira coupling, propargylallenyl isomerization, and [4 + 2] cycloaddition combined via alkylation of carbocyclic enone-based substrates, affording an efficient and stereoselective synthesis of polycyclic skeletons (Shen & Huang, 2008). Given this background, we report the synthesis and crystal structure of the title compound.
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