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Alkylation of 3-nitro-1,2,4-triazole in aqueous alkaline medium in the presence of N-methylmorpholine N-oxide and verification of the structure of the reaction products

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Chemistry of Heterocyclic Compounds Aims and scope

It is shown that alkylation of 3-nitro-1,2,4-triazole with alkyl bromides may be carried out in an aqueous alkaline medium in the presence of N-methylmorpholine N-oxide. Alkylation of 3-nitro-1,2,4-triazole with dibromoethane and propargyl bromide occurs regioselectively with the formation of the substitution products at the N-1 atom of the heterocycle. Alkylation with allyl bromide under similar conditions proceeds with low selectivity leading to regioisomeric substitution products at both N-1 and N-2 atoms. Establishing the structures of the obtained regioisomers by NMR spectroscopy and X-ray crystallography is discussed.

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The work was performed as part of the development program of Russian–Armenian (Slavonic) University, financed by the budget of the Russian Federation. The study was sponsored by the State Science Committee of the Ministry of Education and Science of the Republic of Armenia within the framework of research project № 15T-1D348.

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Authors and Affiliations

  1. Institute of Organic Chemistry of Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan, 0014, Armenia

    Geghetsik B. Zakaryan & Sargis S. Hayotsyan

  2. Molecular Structure Research Center of Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan, 0014, Armenia

    Armen G. Ayvazyan, Rafael A. Tamazyan & Henrik A. Panosyan

  3. Russian–Armenian (Slavonic) University, 123 Hovsep Emin St., Yerevan, 0051, Armenia

    Gevorg G. Danagulyan & Hovhannes S. Attaryan

Authors
  1. Geghetsik B. Zakaryan
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  2. Sargis S. Hayotsyan
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  3. Armen G. Ayvazyan
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  4. Rafael A. Tamazyan
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  5. Henrik A. Panosyan
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  6. Gevorg G. Danagulyan
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  7. Hovhannes S. Attaryan
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Correspondence to Hovhannes S. Attaryan.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(4), 253–256

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Zakaryan, G.B., Hayotsyan, S.S., Ayvazyan, A.G. et al. Alkylation of 3-nitro-1,2,4-triazole in aqueous alkaline medium in the presence of N-methylmorpholine N-oxide and verification of the structure of the reaction products. Chem Heterocycl Comp 52, 253–256 (2016). https://doi.org/10.1007/s10593-016-1870-2

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  • DOI: https://doi.org/10.1007/s10593-016-1870-2

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