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Synthesis of 1,2,3-Triazolo[1,5-а]Pyridin-8-Ium-3-Olates

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Chemistry of Heterocyclic Compounds Aims and scope

Alkylation of sodium 4-acetyl-1-phenyl-1,2,3-triazol-5-olate with α-bromoacetophenones was shown to occur at position 3 of the heterocycle, with the formation of 1,2,3-triazol-3-ium-5-olates. Intramolecular crotonic condensation of the latter led to the formation of 1,2,3-triazolo[1,5-а]pyridin-8-ium-3-olates.

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References

  1. Petronilho, A.; Müller-Bunz, H.; Albrecht, M. Chem. Commun. 2012, 48, 6499.

    Article  CAS  Google Scholar 

  2. Abu-el-Haj, M. J.; McFarland, J. W. US Patent 3933843; Chem. Abstr. 1976, 84, 121847.

    Google Scholar 

  3. Abu-el-Haj, M. J.; McFarland, J. W. US Patent 3939174; Chem. Abstr. 1976, 84, 164788.

    Google Scholar 

  4. Wall, R. J.; Bell, D. R.; Bazzi, R.; Fernandes, A.; Rose, M.; Rowlands, J. C.; Mellor I. R. Toxicology 2012, 302, 140.

    Article  CAS  Google Scholar 

  5. Wamhoff, H. In Comprehensive Heterocyclic Chemestry; Katritzky, A. R., Rees, C., Eds.; Pergamon Press: Oxford, 1984, vol. 5, p. 350.

    Google Scholar 

  6. Blume, F.; Franke, W.; Arndt, F.; Rees, R. US Patent 4859230.

  7. Abbott, P. A.; Bonnert, R. V.; Caffrey, M. V.; Cage, P. A.; Cooke, A. J.; Donald, D. K.; Furber, M.; Hill, S.; Withnall, J. Tetrahedron 2002, 58, 3185.

    Article  CAS  Google Scholar 

  8. Bocian, W.; Wiench, J.; Stefaniak, L.; Webb, G. A. Magn. Reson. Chem. 1996, 34, 453.

    Article  CAS  Google Scholar 

  9. Nein, Yu. I.; Pospelova, T. A.; Bakulev, V. A.; Morzherin, Yu. Yu. Chem. Heterocycl. Compd. 2005, 41, 940. [Khim. Geterotsikl. Soedin. 2005, 1107.]

    Article  CAS  Google Scholar 

  10. Nein, Yu. I.; Gladkova, S. V.; Pospelova, T. A.; Morzherin, Yu. Yu. Chem. Heterocycl. Compd. 2006, 42, 1472. [Khim. Geterotsikl. Soedin. 2006, 1714.]

    Article  CAS  Google Scholar 

  11. Nein, Yu. I.; Morzherin, Yu. Yu.; Rozin, Yu. A.; Bakulev, V. A. Chem. Heterocycl. Compd. 2002, 38, 1104. [Khim. Geterotsikl. Soedin. 2002, 1302.]

    Article  Google Scholar 

  12. Nein, Yu. I.; Polyakova, A. Yu.; Morzherin, Yu. Yu.; Savel'eva, E. A.; Rozin, Yu. A.; Bakulev, V. A. Russ. J. Org. Chem., 2004, 40, 879. [Zh. Org. Khim. 2004, 40, 917.]

    Article  CAS  Google Scholar 

  13. Nein, Yu. I.; Morzherin, Yu. Yu. Chem. Heterocycl. Compd. 2014, 50, 1021. [Khim. Geterotsikl. Soedin. 2014, 1107.]

    Article  CAS  Google Scholar 

  14. Savini, L.; Massarelli, P.; Chiasserini, L.; Pellerano, C.; Bruni, G. Farmaco 1994, 49, 633.

    CAS  Google Scholar 

  15. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

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The results were obtained within the framework of the State Assignment for sscientific activity No. 4.560.2014-K from the the Ministry of Education and Science of the Russian Federation and with support from the Russian Foundation for Basic Research (grant 13-03-00137).

The authors are grateful to the Laboratory of Complex Investigations and Expert Evaluation of Organic Materials, Collective Use Center of the Ural Federal University, for acquiring NMR spectra of the obtained compounds.

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Authors and Affiliations

  1. Ural Federal University, 19 Mira St., Yekaterinburg, 620002, Russia

    Inna S. Khazhieva, Pavel M. Demkin, Julia I. Nein, Tatiana V. Glukhareva & Yuri Yu. Morzherin

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  1. Inna S. Khazhieva
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  2. Pavel M. Demkin
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  3. Julia I. Nein
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  4. Tatiana V. Glukhareva
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  5. Yuri Yu. Morzherin
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Correspondence to Yuri Yu. Morzherin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(2), 199–202

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Khazhieva, I.S., Demkin, P.M., Nein, J.I. et al. Synthesis of 1,2,3-Triazolo[1,5-а]Pyridin-8-Ium-3-Olates. Chem Heterocycl Comp 51, 199–202 (2015). https://doi.org/10.1007/s10593-015-1681-x

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  • DOI: https://doi.org/10.1007/s10593-015-1681-x

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