Synthesis 2018; 50(24): 4889-4896
DOI: 10.1055/s-0037-1610244
paper
© Georg Thieme Verlag Stuttgart · New York

First Example of C–H Functionalisation in the 6-Nitroazolo[5,1-c]triazine Series

Evgeny B. Gorbunov*
a  Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskaya St. 22, Ekaterinburg 620041, Russian Federation
b  Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation   Email: nitrozo@yandex.ru
,
Evgeny N. Ulomsky
a  Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskaya St. 22, Ekaterinburg 620041, Russian Federation
b  Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation   Email: nitrozo@yandex.ru
,
Egor K. Voinkov
b  Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation   Email: nitrozo@yandex.ru
,
Roman A. Drokin
b  Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation   Email: nitrozo@yandex.ru
,
Daniil N. Lyapustin
b  Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation   Email: nitrozo@yandex.ru
,
Gennadiy L. Rusinov
a  Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskaya St. 22, Ekaterinburg 620041, Russian Federation
b  Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation   Email: nitrozo@yandex.ru
,
Vladimir L. Rusinov
a  Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskaya St. 22, Ekaterinburg 620041, Russian Federation
b  Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation   Email: nitrozo@yandex.ru
,
Valery N. Charushin
a  Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskaya St. 22, Ekaterinburg 620041, Russian Federation
b  Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation   Email: nitrozo@yandex.ru
,
Oleg N. Chupakhin
a  Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskaya St. 22, Ekaterinburg 620041, Russian Federation
b  Ural Federal University named after the First President of Russia B. N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation   Email: nitrozo@yandex.ru
› Author Affiliations
This research study was carried out with the financial support of the Russian Ministry of Education and Science (State contract 4.6351.2017/8.9). NMR spectra and elemental analyses were covered by a grant from the Russian Science Foundation (project 16-13-00008).
Further Information

Publication History

Received: 18 June 2018

Accepted after revision: 19 July 2018

Publication Date:
23 August 2018 (online)


Abstract

The reaction of 6-nitroazolo[5,1-c]triazines with O-methylated polyphenols, with pyrrole and its benzo analogues, and with thiophene has been studied. Methods for the reduction of the nitro group in the resulting σH-adducts and subsequent oxidative aromatisation have been developed.

Supporting Information

 
  • References


    • For selected reviews on the nucleophilic aromatic substitution of hydrogen (SN H reactions), see:
    • 2a Chupakhin ON. Charushin VN. Van der Plas HC. Nucleophilic Aromatic Substitution of Hydrogen . Academic Press; New York/San Diego: 1994: 367
    • 2b Charushin VN. Chupakhin ON. Pure Appl. Chem. 2004; 76: 1621
    • 2c Charushin VN. Chupakhin ON. Mendeleev Commun. 2007; 17: 249
    • 2d Makosza M. Wojciechowski K. Chem. Rev. 2004; 104: 2631
    • 2e Makosza M. Chem. Soc. Rev. 2010; 39: 2855
    • 2f Charushin VN. Chupakhin ON. In Topics in Heterocyclic Chemistry . Vol. 5. Charushin VN. Chupakhin ON. Springer International Publishing; Switzerland: 2013: 1-50
    • 2g Makosza M. Wojciechowski K. In Topics in Heterocyclic Chemistry . Vol. 5. Charushin VN. Chupakhin ON. Springer International Publishing; Switzerland: 2013: 51-105
    • 3a Makosza M. Winiarski J. Acc. Chem. Res. 1987; 20: 282
    • 3b Goumont R. Jan E. Makosza M. Terrier F. Org. Biomol. Chem. 2003; 1: 2192
  • 4 Rusinov VL. Myasnikov AV. Pilicheva TL. Chupakhin ON. Kiprianova EA. Garagulya AD. Pharm. Chem. J. 1990; 24: 52
  • 5 Rusinov GL. Gorbunov EB. Charushin VN. Chupakhin ON. Tetrahedron Lett. 2007; 48: 5873
  • 6 Rusinov VL. Pilicheva TL. Chupakhin ON. Klyuev NA. Allakhaverdieva DT. Chem. Heterocycl. Compd. 1986; 22: 543
  • 7 Voinkov EK. Ulomsky EN. Rusinov VL. Drokin RA. Fedotov VV. Gorbunov EB. Mendeleev Commun. 2017; 27: 285