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The Mannich reaction in the synthesis of N,S-containing heterocycles 8. Aminomethylation of 3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates as a method for the synthesis of new functionally substituted 3,7-diazabicyclo[3.3.1]nonane derivatives

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Abstract

Aminomethylation of 3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates upon treatment with primary amines and excess formaldehyde leads to 3,7-diazabicyclo[3.3.1]nonane derivatives. N-Methylmorpholinium 4-(2-chlorophenyl)-3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate was obtained by the reaction of (E)-3-(2-chlorophenyl)-2-cyanoprop-2-enethioamide with 1-cyanoacetyl-3,5-dimethylpyrazole and N-methylmorpholine in acetone in quantitative yield.

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Authors and Affiliations

  1. State Enterprise “Luganskstandartmetrology”, 50 ul. Timiryazeva, 91021, Lugansk, Ukraine

    V. V. Dotsenko

  2. V. Dal’ East-Ukrainian National University, 20a kv. Molodyozhnyi, 91034, Lugansk, Ukraine

    V. V. Dotsenko & S. G. Krivokolysko

  3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. P. Litvinov

Authors
  1. V. V. Dotsenko
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  2. S. G. Krivokolysko
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  3. V. P. Litvinov
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Correspondence to V. V. Dotsenko.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2397–2400, December, 2007.

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Dotsenko, V.V., Krivokolysko, S.G. & Litvinov, V.P. The Mannich reaction in the synthesis of N,S-containing heterocycles 8. Aminomethylation of 3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates as a method for the synthesis of new functionally substituted 3,7-diazabicyclo[3.3.1]nonane derivatives. Russ Chem Bull 56, 2482–2486 (2007). https://doi.org/10.1007/s11172-007-0395-3

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  • DOI: https://doi.org/10.1007/s11172-007-0395-3

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