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A Convenient Mannich-Type One-Pot Synthesis of Pyrimido[6,1-b][1,3,5]thiadiazines

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Summary.

3-(Het)aryl-2-cyanoprop-2-enethioamides easily reacted with primary amines and excessive formaldehyde under mild conditions to afford pyrimido[6,1-b][1,3,5]thiadiazine derivatives in moderate yields. Furthermore, 2-cyano-2-cyclohexylideneethanethioamide reacted in the similar Mannich-type manner to give spiro-conjugated pyrimido-1,3,5-thiadiazines. The structure of 3,7-dibenzyl-8-(fur-2-yl)-3,4,7,8-tetrahydro-2H,6H-pyrimido[6,1-b][1,3,5]thiadiazine-9-carbonitrile was determined by X-ray diffraction analysis.

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Authors and Affiliations

  1. Chemistry Department, Vladimir Dal’ East Ukrainian National University, Lugansk, Ukraine

    Victor V. Dotsenko, Konstantin A. Frolov & Sergey G. Krivokolysko

  2. Institute of Organic Chemistry, National Academy of Sciences, Kiev, Ukraine

    Alexander N. Chernega

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

    Victor P. Litvinov

Authors
  1. Victor V. Dotsenko
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  2. Konstantin A. Frolov
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  3. Sergey G. Krivokolysko
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  4. Alexander N. Chernega
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  5. Victor P. Litvinov
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Correspondence to Victor V. Dotsenko.

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Dotsenko, V., Frolov, K., Krivokolysko, S. et al. A Convenient Mannich-Type One-Pot Synthesis of Pyrimido[6,1-b][1,3,5]thiadiazines. Monatsh. Chem. 137, 1089–1098 (2006). https://doi.org/10.1007/s00706-006-0512-2

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  • DOI: https://doi.org/10.1007/s00706-006-0512-2

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