Journal of the Korean Applied Science and Technology (한국응용과학기술학회지)

The Korean Society of Applied Science and Technology (한국응용과학기술학회)
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Diazotiation of Aminopyridines

아미노피리딘의 디아조화 반응

  • Chung, Yeong-Jin (School of Fire & Disaster Prevention, Samcheok National University)
  • Published : 2004.09.30
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Abstract

Diazotization of three aminopyridine such as 3-amino-2-chloropyridine, 5-amino-2-chloropyridine, and 3-aminopyridine were investigated. Preparation of pyridinediazonium tetrafluoroborates were carried out employing two different methods. Diazotization of aminopyridines with a chlorine substituent in the pyridine ring were conducted in acidic aqueous solution with sodium nitrite in 70% and 74% yields respectively. 3-Pyridinediazonium tetrafluoroborate without any ring subsituent was unstable in an aquous solution and the diazotiation of 3-aminopyridine was proceded in an anhydrous methylene chloride-etherial $BF_3$ solution with tert-butyl nitrite in 40% yield.

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References

  1. S. Patai, 'The Chemistry of Diazonium and Diazo Groups', John Wiley & Sons, Inc., Chapter 14., New York, 1978; M. J. S. Carpes and C. R. D. Correia, Heck Arylations of N-Acyl-3-Pyrroline and N-Acyl-1,2,5,6-Tetrahydropyridine with Aryldiazonium Salts. Short Syntheses of Aryl $\gamma$- and $\delta$-Lactams, Baclofen Homobaclofen and Analogues, Tetrahedron Letters, 43, 741 (2002) https://doi.org/10.1016/S0040-4039(01)02267-5
  2. R. A. Bartsch and I. W. Yang, Polyethylene Glycol as Phasetransfer Catalyst for Aryldiazonium Salts Reactions, Tetrahedron Lett, 2503 (1979)
  3. S. H. Korzeniowski and G. W. Gokel, Crown-Cation Complex Effects. IV. Crown Ether and Quaternary Ion Mediated Displacements in Aryldiazonium Compounds, Tetrahedron Lett, 19, 1637 (1977)
  4. I. W. Yang and Y. J. Chung, Optimization of an Aryne Adduct Genarated from 3-Ch1orobenzenediazonium Tetrafluoro-borate (I), J. Korean Ind. Eng. Chem., 14(5), 641 (2003); H. Pellisser and M. Santelli, The Use of Arynes in Organic Synthesis, Tetrahedron, 59, 2575 (2003) https://doi.org/10.1016/S0040-4020(03)00296-5
  5. H. Pellissier and M. Santelli, The Use of Arynes in Organic Synthesis, Tetrahedron, 59, 2575 (2003) https://doi.org/10.1016/S0040-4020(03)00296-5
  6. R. A. Bartsch and I. W. Yang, Phase Tranfer Catalyzed Synthesis of Imidazoles from o-Alkylbenzendiazonium Tetrafluo-roborates, J. Heterocyclic Chem, 21, 1063 (1984) https://doi.org/10.1002/jhet.5570210428
  7. A. McKillop, 'Comprehensive Heterocyclic Chemistry' Vol. 5, p. 11, Elsvier, Oxford (1996)
  8. A. Roe, Preparation of Aromatic Fluorine Compounds from Diazoniun Fluoroborstes, Org. React., 5, 193 (1949)
  9. M. P. Doyle and W. J. Bryker, Alkyl Nitrite-Metal Halide Deamination Reactions. 6. Direct Synthesis of Arenediazonium Tetrafluoroborate Salts from Aromatic Amines, tert-Butyl Nitrite, and Boron Trifuororide Etherate in Anhydrous Media, J. Org. Chem., 44, 1572 (1979) https://doi.org/10.1021/jo01323a048