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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 3
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Original Articles

Application of the Curtius Rearrangement in a Convenient Preparation of 3-Aminopyrazinecarboxylic Acid, Methyl Ester

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Pages 617-622 | Received 06 Jun 1995, Published online: 21 Aug 2006

References

  • Barlin , G. B. 1982 . The Pyrazines, The Chemistry of Heterocyclic Compounds - A Series of Monographs , pp.247 – 377 . New York : John Wiley & Sons .
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  • Weijlard , J. , Tishler , M. and Erickson , A. E. 1945 . J. Am. Chem. Soc. , 67 : 802 – 806 .
  • Ellingson , R. C. , Henry , R. C. and McDonald , F. G. 1945 . J. Am. Chem. Soc. , 67 : 1711 – 1713 .
  • Buckland , P. R. 1980 . J. Heterocycl. Chem. , 17 : 397 – 398 .
  • Solomons , I. A. and Spoerri , P. 1953 . J. Am. Chem. Soc. , 75 : 679 – 681 .
  • Magnien , E. and Baltzly , R. 1958 . J. Org. Chem. , 23 : 2029 – 2032 .
  • Baumgarten , H. E. , Smith , H. L. and Staklis , A. 1975 . J. Org. Chem. , 40 : 3554 – 3561 .
  • Smith , P. A. S. 1947 . Organic Reactions III , pp.337 – 450 . New York : John Wiley & Sons .
  • Jones , R. G. and McLaughlin , K. C. 1963 . Organic Synthesis, Collective , Vol IV , pp.824 – 827 . New York : John Wiley & Sons .
  • Moisture will hydrolyze this compound to furnish 2,3-pyrazinedicarboxylic acid.
  • Organic azides may be explosive, thus, caution should be exercised. However, we have not encountered any problems up to a 500 g scale of this reaction in our lab.

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