A Convenient, One-Stage Transformation of 2,6-Diethyl-4(H)-pyranone to 4-Amino-2,6-diethylpyridine

References

• Yates , P. , Hand , E. I. , Singh , P. , Roy , S. K. and Still , I. W.J. 1969 . J. Org. Chem. , 34 : 4046 We found that the three-stage method described herein can be reduced to a single stage simply by the gradual addition of water to the hot sulphuric acid/propionic acid reaction mixture containing the initial product. 2,6-Diethyl-4(H)pyranone is formed directly. Separation from the propionic acid can be achieved by adding methanol to the mixture (thereby forming methyl propionate) and distillation. The yield from acetone dicarboxylic acid is 55%.
   Google Scholar
• Parisi , F. , Bovina , P. and Quilico , A. 1962 . Gazz. Chim. Ital. , 92 : 1138
   Google Scholar
• Bradbury , R. H. , Edwards , M. P. and Ratcliffe , A. H. EP 499415 . 19 August 1992 .
   Google Scholar
• Ellis , G. P. 1984 . Comprehensive Heterocyclic Chemistry , Edited by: Boulton , A. J. and McKillop , A. Vol 3 , Pergamon Press .
   Google Scholar
• Van Allen , J. A. , Chie Chang , S. and Reynolds , G. A. 1974 . J. Heterocyclic Chem. , 11 : 195
   Google Scholar
• Kato , T. , Sato , M. and Kimura , H. 1979 . J. Chem. Soc., Perkin Trans. I , : 529 The competitive formation of resorcinol derivatives during the cyclisation of 1,3,5-triketones is well-known. See, for example
   Google Scholar