Synthesis 2016; 48(24): 4525-4532
DOI: 10.1055/s-0036-1588304
paper
© Georg Thieme Verlag Stuttgart · New York

A New Powerful Approach to Multi-Substituted 3(2H)-Furanones via Brønsted Acid-Catalyzed Reactions of 4-Diazodihydrofuran-3-ones

Authors

  • Jury J. Medvedev

    Saint-Petersburg State University, Institute of Chemistry, Universitetskii pr. 26, Petrodvorets, St. Petersburg 198504, Russian Federation   eMail: vnikola@VN6646.spb.edu
  • Dmitrii V. Semenok

    Saint-Petersburg State University, Institute of Chemistry, Universitetskii pr. 26, Petrodvorets, St. Petersburg 198504, Russian Federation   eMail: vnikola@VN6646.spb.edu
  • Xenia V. Azarova

    Saint-Petersburg State University, Institute of Chemistry, Universitetskii pr. 26, Petrodvorets, St. Petersburg 198504, Russian Federation   eMail: vnikola@VN6646.spb.edu
  • Liudmila L. Rodina

    Saint-Petersburg State University, Institute of Chemistry, Universitetskii pr. 26, Petrodvorets, St. Petersburg 198504, Russian Federation   eMail: vnikola@VN6646.spb.edu
  • Valerij A. Nikolaev*

    Saint-Petersburg State University, Institute of Chemistry, Universitetskii pr. 26, Petrodvorets, St. Petersburg 198504, Russian Federation   eMail: vnikola@VN6646.spb.edu
Weitere Informationen

Publikationsverlauf

Received: 03. Juli 2016

Accepted after revision: 02. August 2016

Publikationsdatum:
14. September 2016 (online)


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Abstract

The interaction of 5,5-dialkyl(diaryl)-substituted 4-diazo-3(2H)furanones with Brønsted acids (TFA, TsOH, etc.) causes elimination of nitrogen accompanied by 1,2-nucleophilic rearrangement, giving rise to exclusive formation of 4,5-dialkyl(diaryl)-substituted 3(2Н)-furanones, ring-fused 3(2H)-furanones, and phenanthro[9,10-b]furan-3(2H)-ones in yields of up to 99%. The reaction is a new highly efficient way for the synthesis of multisubstituted 3(2Н)furanones.

Supporting Information