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Reaction of 3-Alkynylquinoxaline-2-carbonitriles with Sodium Azide: an Experimental and Theoretical Study

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 3-alkynylquinoxaline-2-carbonitriles with sodium azide in DMF at 60 °C leads to the formation of 4,5-disubstituted 2H-1,2,3-triazoles in 38-82% yields. The analogous reaction in toluene in the presence of AlCl3 takes place as a tandem process involving 1,3-dipolar cycloaddition of the azide ion to the nitrile group followed by 6-endo-digonal cyclization with the formation of 5-aryl-tetrazolo[1′,5′:1,3]pyrido[3,4-b]quinoxalines.

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The work was carried out with financial support from the Russian Foundation for Basic Research (grant No. 11-03-00079).

The authors thank Z. A. Starikova* (Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow) for carrying out the X-ray structural investigation.

*Deceased

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Authors and Affiliations

  1. Southern Federal University, 7 Zorge St., Rostov-on-the-Don, 344090, Russia

    A. S. Tyaglivy, D. V. Steglenko & A. V. Gulevskaya

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  1. A. S. Tyaglivy
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  2. D. V. Steglenko
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  3. A. V. Gulevskaya
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Correspondence to A. V. Gulevskaya.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1346-1355, September, 2013.

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Tyaglivy, A.S., Steglenko, D.V. & Gulevskaya, A.V. Reaction of 3-Alkynylquinoxaline-2-carbonitriles with Sodium Azide: an Experimental and Theoretical Study. Chem Heterocycl Comp 49, 1255–1263 (2013). https://doi.org/10.1007/s10593-013-1373-3

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