Copper-Catalyzed Sulfonylation/Cyclization of Pent-4-ynamides toward Sulfonyl-Functionalized Pyrrol-2-ones

Abstract

A domino sulfonylation/intramolecular C–N coupling/dehydrogenation reaction was realized between pent-4-ynamides and sulfonyl chlorides by catalysis of Cu­(acac)2 and 2,2′-bis­(diphenylphosphanyl)-1,1′-binaphthalene. The reaction provides a convenient approach to sulfonyl-functionalized pyrrol-2-ones. This method can also be applied to the synthesis of 3-alkylidene isoindolinones from 2-ethynyl-benzamides.

Rh(III)-Catalyzed [4 + 1] Annulation of Benzamides with Vinyl Cyclic Carbonates for the Synthesis of Isoindolinones

“…As depicted in Figure , impatien A, aristoyagonine, pestalachloride A, and pagoclone are representative biologically active compounds displaying antifungal, anxiolytic, or aldose-reductase-inhibiting activities. In recent years, considerable efforts have been devoted to synthesize isoindolinones, and various methods such as cyclization of o -alkenyls or o -alkynylbenzamides, carbonylation of 2-aminomethylaryl halides, lactamization of o -(aminomethyl)­benzoic acids, and transition-metal-catalyzed difunctionalization of enamides have been established. However, these approaches usually suffered from harsh conditions, prefunctionalization of the substrates, and limited substrate scope.…”

Regioselective Construction of Indolylated Cyclic Tetrasubstituted Carbon Centers through Brønsted Acid‐Catalyzed Dearomative Skeletal Rearrangement of Azofurans

“…[4g] With these appealing contributions in mind, many reliable synthetic strategies have been established to access 1,5-dihydro-2H-pyrrol-2ones over the years. [5] However, there are few reports on the assembly of N-substituted 2H-pyrrol-2-ones bearing cyclic tetrasubstituted carbons, [6] probably because of the inherent difficulty in overcoming the congested nature of tetrasubstituted carbons. [7] Consequently, developing a new and widely used synthetic technology for the synthesis of cyclic tetrasubstituted carbon-containing pyrrol-2-ones is highly desirable, considering the potential of using these molecules for downstream studies in medicinal chemistry.…”