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http://dx.doi.org/10.12925/jkocs.2004.21.3.8

Diazotiation of Aminopyridines  

Chung, Yeong-Jin (School of Fire & Disaster Prevention, Samcheok National University)
Publication Information
Journal of the Korean Applied Science and Technology / v.21, no.3, 2004 , pp. 246-251 More about this Journal
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.
Keywords
diazotiation; aminopyridine; pyridinediazonium tetrafluoroborates;
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  • Reference
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)   DOI   ScienceOn
2 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)   DOI
3 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)   DOI   ScienceOn
4 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)
5 H. Pellissier and M. Santelli, The Use of Arynes in Organic Synthesis, Tetrahedron, 59, 2575 (2003)   DOI   ScienceOn
6 A. McKillop, 'Comprehensive Heterocyclic Chemistry' Vol. 5, p. 11, Elsvier, Oxford (1996)
7 R. A. Bartsch and I. W. Yang, Phase Tranfer Catalyzed Synthesis of Imidazoles from o-Alkylbenzendiazonium Tetrafluo-roborates, J. Heterocyclic Chem, 21, 1063 (1984)   DOI
8 A. Roe, Preparation of Aromatic Fluorine Compounds from Diazoniun Fluoroborstes, Org. React., 5, 193 (1949)
9 R. A. Bartsch and I. W. Yang, Polyethylene Glycol as Phasetransfer Catalyst for Aryldiazonium Salts Reactions, Tetrahedron Lett, 2503 (1979)