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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 15
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Original Articles

Synthesis of 3-Acyl and 3-Carboalkoxyfurans by the Ceric Ammonium Nitrate Promoted Addition of 1,3-Dicarbonyl Compounds to Vinylic Acetates

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Pages 1841-1846 | Published online: 06 Dec 2006

References

  • Belg. Patent 902944 . C.A., 1986, 105, 172273; Shuichi, M. Jp. Patent 86263935, C.A., 1987, 106, 178121; Nunomura, M. and Yokotsuka, T., Agrie. Biol. Chem., 1984, 48, 1753, See, for example, Roussell-UCLAF
  • Baciocchi , E. , Civitarese , G. and Ruzziconi , R. 1987 . Tetrahedron Lett. , 28 : 5357
  • Baciocchi , E. and Ruzziconi , R. 1986 . Gazz. Chim. It. , 106 : 671
  • Giese , B. 1983 . Angew. Chem. Int. Ed. Engl. , 22 : 753
  • Miyashita , M. , Kumazowa , T. and Yoshikoshi , A. 1978 . J. Chem. Soc. Chem. Commun. , : 362
  • March , J. 1977 . “Advanced Organic Chemistry” , 82 New York : McGraw-Hill . 1 hr reflux, in toluene, in the presence of p-toluenesulfonic acid, was sufficient in our case
  • Solid 1,3-dicarbonyl compounds are dissolved in a small amount of acetone
  • This step is useful to increase the yield in dihydro-furan derivatives, in so far as it favors the ring closure with displacement of nitrate ion of the first formed adduct RCCOR'OCHCHR CONO2 HOCOCH3. Sodium bicarbonate is needed to neutralize nitric acid which forms in this step

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