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A Double Mannich-type Reaction in the 1,4,5,6-Tetrahydropyridine-2-thiolate Series: A Convenient Approach to Functionalized 3,7-Diazabicyclo[3.3.1]nonane Derivatives

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Summary.

The reaction of N-methylmorpholinium 5-alkoxy-carbonyl-4-aryl-3-cyano-2-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with primary amines and formaldehyde under mild conditions afforded 7-substituted alkyl 9-aryl-5-cyano-2-oxo-4-thioxo-3,7-diazabicyclo[3.3.1]nonane-1-carboxylates in fair to good yields (52–74%).

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Authors and Affiliations

  1. “ChemEx” Laboratory, Vladimir Dal’ East Ukrainian National University, Lugansk, Ukraine

    Victor V. Dotsenko & Sergey G. Krivokolysko

  2. Russian Academy of Sciences, Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation

    Victor P. Litvinov

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

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Third author was Deceased on February 26, 2007

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Dotsenko, V., Krivokolysko, S. & Litvinov, V. A Double Mannich-type Reaction in the 1,4,5,6-Tetrahydropyridine-2-thiolate Series: A Convenient Approach to Functionalized 3,7-Diazabicyclo[3.3.1]nonane Derivatives. Monatsh. Chem. 138, 489–494 (2007). https://doi.org/10.1007/s00706-007-0620-7

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