Synthesis of N-substituted aminomethylene-benzofuran-2-ones

One-pot domino syntheses of 3-alkyl-3- N -substituted aminobenzofuran-2(3 H )-ones based on alkali-promoted Michael addition and lactonization

“…They serve as important scaffolds for biologically active compounds with interesting cytotoxic and pharmacological properties [4,5]. Furthermore, they play a role in functionalized organic molecules used in materials, supramolecular and polymer chemistry [6][7][8][9]. Many of these compounds feature an aminated quaternary stereocentre at the C3 position of the 2-coumaranone ring.…”

Organocatalytic Aza-Friedel–Crafts/Lactonization Domino Reaction of Naphthols and Phenols with 2-Acetamidoacrylate to Naphtho- and Benzofuranones Bearing a Quaternary Center at the C3 Position

“…The structural motifs of 3,3-disubstituted benzo- and naphthofuranone are common in a variety of medicinally effective natural products . They are also found as synthetic intermediates of valuable biologically active compounds that possess interesting cytotoxic and pharmacological properties as well as in functionalized compounds with applications in materials, supramolecular, and polymer chemistry . Many of these structures feature a chiral quaternary stereocenter at the C3 position of the heterocyclic ring (Figure ).…”

Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones

“…Benzofuranones as one of the important building blocks exist in a variety of natural products 9 and potential medicines. 10 The enantioselective synthesis of chiral benzofuranones remains a considerable challenge, 11 especially in the field of construction of a chiral spiro-quaternary center at the C3 position of benzofuranones. 12 As part of our ongoing investigation on phosphine-catalyzed asymmetric cycloaddition, 13 we wish to report a spiro phosphine ( R )-SITCP 14 catalyzed asymmetric [3 + 2] cycloaddition of allenic esters with benzofuranones, furnishing the spiro cycloadducts in good yields with excellent regio-, diastereo- and enantioselectivities, by adjusting the substituents of the allenic esters to obtain both the α-addition and γ-addition products, and using rational DFT calculations to reveal the reason for the regioselectivity.…”