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

作者：Medvedev Jury J; Semenok Dmitrii V; Azarova Xenia V; Rodina Liudmila L; Nikolaev Valerij A^*

来源：Synthesis (Germany), 2016, 48(24): 4525-4532.

DOI：10.1055/s-0036-1588304

• diazo compounds
• Bronsted acids
• catalysis
• rearrangement
• carbocation

The interaction of 5,5-dialkyl(diaryl)-substituted 4-diazo-3(2H)furanones with Bronsted 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(2H)-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(2H)furanones.

• 出版日期2016-12