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

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 σ^H-adducts and subsequent oxidative aromatisation have been developed.

Key words

6-nitroazolo[5,1-c]triazines - σ^H-adducts - nitro group reduction - nucleophilic aromatic substitution of hydrogen - C–H functionalisation

• References

• 1a Topics in Current Chemistry . Vol. 292. Yu J.-Q. Shi Z. Springer; Berlin/Heidelberg: 2010: 1-379
• 1b Wencel-Delord J. Glorius F. Nat. Chem. 2013; 5: 369
• 1c Topics in Organometallic Chemistry . Vol. 55. Dixneuf PH. Doucet H. Springer International Publishing; Switzerland: 2016: 1-260

For selected reviews on the nucleophilic aromatic substitution of hydrogen (S_N ^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