Abstract
In the title compound, C20H19NO5, the central six-membered ring has a slightly distorted half-chair conformation, with puckering parameters of Q T = 0.3387 (11) Å, θ = 49.11 (19)° and φ = 167.3 (2)°. The conformation of the fused pyrrolidine ring is that of an envelope. Mol-ecules are connected by inter-molecular C-H⋯O hydrogen bonds, C-H⋯π inter-actions and π-π stacking inter-actions [centroid-to-centroid distance = 3.9536 (11) Å, with a slippage of 2.047 Å], forming a three-dimensional network. The most important contributions to the surface contacts are from H⋯H (46.3%), O⋯H/H⋯O (31.5%) and C⋯H/H⋯C (17.3%) inter-actions, as concluded from a Hirshfeld surface analysis.
Highlights
In the title compound, C20H19NO5, the central six-membered ring has a slightly distorted half-chair conformation, with puckering parameters of QT = 0.3387 (11) A, = 49.11 (19) and ’ = 167.3 (2)
The most important contributions to the surface contacts are from HÁ Á ÁH (46.3%), OÁ Á ÁH/HÁ Á ÁO
An IMDAV reaction is a useful tool for the one-step synthesis of benzofurans, indoles and benzothiophenes annulated with other carbo- and heterocycles (Krishna et al, 2020)
Summary
This work is a continuation of Diels–Alder reaction studies on vinylarene systems, previously carried out for the tandem acylation/[4 + 2] cycloaddition between 3-(aryl)allylamines and maleic anhydrides or acryloyl chlorides as an example of an IMDAV (the acronym for Intra Molecular Diels–Alder Vinylarene) reaction. Our group carried out a domino-sequence reaction involving acylation/IMDAV/ aromatization steps, which led to the target furo- and thieno[2,3-f]isoindoles (Zubkov et al, 2016; Horak et al, 2015, 2017; Nadirova et al, 2020). This process does not stop at the furo[2,3-f]isoindole (4) formation but is continued by an oxidation step yielding the 8-oxofuro[2,3f]isoindole (5) (Fig. 1). We highlight the role of weak interactions in the structural features of 5
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