Abstract
The crystal structures are reported for two unsubstituted arylnaphthalene lactones, 4-phenylnaphtho[2,3-c]furan-1(3H)-one (2), 9-phenylnaphtho[2,3-c]furan-1(3H)-one (3) and a non-aromatic dihydro arylnaphthene lactone, 3a,4-dihydro-9-phenylnaphtho[2,3-c]furan-1(3H)-one (5). There are only minor differences in the geometrical parameters of these structures. However, in certain cases, both isomers of arylnaphthalene lactones (termed Type I and Type II) were found in the same asymmetric unit cell.
Highlights
Arylnaphtalene lactones are a subclass of lignans that can be extracted from a wide range of species such as Justicia [1]
We focused on the heat-mediated Dehydro-Diels–Alder synthetic approach to these arylnaphthalene lactones [16,17,18]
The investigation of a Dehydro-Diels–Alder synthetic method for the synthesis of arylnapthalene lactones led to a set of high yield crystalline products
Summary
Arylnaphtalene lactones are a subclass of lignans that can be extracted from a wide range of species such as Justicia [1]. Of the many synthetic routes explored to efficiently obtain these arylnapthalene lactones, intramolecular Diels–Alder methods [8], multicomponent methods [9], Suzuki cross-coupling reactions [10], oxidative cyclizations [11], silver-catalyzed one-pot synthesis [12] and metal-catalyzed annulations [13,14,15] are just a sample of the possible synthetic pathways available Each of these approaches allow access to a large variety of original lactones, bearing a variety of substituents along the conjugated backbone. Such a structural investigation is an essential element for a better understanding of the structure–property relationship and the bioactivities associated with these lignans These crystal structures could provide the insight necessary to implement further modification to their conjugated backbones without interfering with their overall structural scaffolds.
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