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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

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

Dong Jun J Du Hongguang H Xu Jiaxi J

RSC advances 20190812 43

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 ...[more]

PMID: 35528645

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