An efficient synthesis of multisubstituted 4-nitrobuta-1,3-dien-1-amines and application in cyclisation reactions

Brigita Vigante, Aiva Plotniece, Martins Rucins, Marina Petrova, Ruslan Muhamadejev, Karlis Pajuste, Sergey Belyakov, Yuriy G. Shermolovich, Arkadij Sobolev (Coresponding Author)

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


The synthesis of multisubstituted 4-nitrobuta-1,3-dien-1-amines (nitrodienamines) from 3-aminocrotonates and nitroacetaldehyde potassium salt, has been performed in 45–89% yields. This one-step protocol works efficiently with a broad range of N-H and N-substituted 3-aminocrotonates and delivers both primary and secondary nitrodienamines. In addition, the possible variations of the substituents at the positions 2 and 3 of 4-nitrobuta-1,3-dien-1-amine have been shown. Generally, the yields of secondary 4-nitrobuta-1,3-dien-1-amines were lower than those of primary ones. The synthetic usefulness of obtained 4-nitrobuta-1,3-dien-1-amines has also been demonstrated by achieving the synthesis of multisubstituted 5-nitro-1,6-dihydropyridines in two-component cyclocondensation reactions of 4-nitrobuta-1,3-dien-1-amines with aromatic or aliphatic aldehydes. Lastly, diverse N-H and N-substituted 5-nitro-1,6-dihydropyridines have been obtained in 35–87% yields.

Original languageEnglish
Pages (from-to)2596-2607
Number of pages12
Issue number21
Publication statusPublished - 24 May 2018
Externally publishedYes


  • 3-Aminocrotonate
  • 4-Nitrobuta-1,3-dien-1-amine
  • Cyclisation reaction
  • Dihydropyridines
  • Nitroacetaldehyde potassium salt
  • Nitrodienamine

Field of Science*

  • 1.4 Chemical sciences
  • 3.1 Basic medicine

Publication Type*

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database


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