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Synthesis 2016; 48(24): 4525-4532
DOI: 10.1055/s-0036-1588304
DOI: 10.1055/s-0036-1588304
paper
A New Powerful Approach to Multi-Substituted 3(2H)-Furanones via Brønsted Acid-Catalyzed Reactions of 4-Diazodihydrofuran-3-ones
Further Information
Publication History
Received: 03 July 2016
Accepted after revision: 02 August 2016
Publication Date:
14 September 2016 (online)
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
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588304.
- Supporting Information
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For the synthesis of initial 4-diazo-3(2Н)-dihydrofuranones 1, see: