Regiospecific synthesis of polysubstituted furans with mono- to tricarboxylates from various sulfonium acylmethylides and acetylenic esters.

ABSTRACT: Polysubstituted furans were prepared in moderate to good yields from various sulfur ylides and alkyl acetylenic carboxylates. The direct reactions of dimethylsulfonium acylmethylides with dialkyl acetylenedicarboxylates afforded dialkyl furan-3,4-dicarboxylates through a tandem sequence of Michael addition, intramolecular nucleophilic addition, 4π ring opening, intramolecular Michael addition, and elimination. The method was extended to synthesize furan-3-carboxylate, -2,4-dicarboxylates, and -2,3,4-tricarboxylates as well. The current method provides a direct and simple strategy in the synthesis of structurally diverse polysubstituted furans with mono to tricarboxylate groups from safe and readily available dimethylsulfonium acylmethylides and different alkyl acetylenic carboxylates.

SUBMITTER: Dong J 

PROVIDER: S-EPMC9070029 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature