An Efficient Synthesis of Multisubstituted 4-Nitrobuta-1,3-Dien-1-Amines and Application in Cyclisation Reactions
Tetrahedron 2018
B. Vīgante, A. Plotniece, M. Ruciņš, M. Petrova, R. Muhamadejev, K. Pajuste, Sergejs Beļakovs, Y.G. Shermolovich, A. Sobolev

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.


Atslēgas vārdi
multisubstituted 4-nitrobuta-1,3-dien-1-amines, cyclisation reactions
DOI
10.1016/j.tet.2018.03.075
Hipersaite
https://www.sciencedirect.com/science/article/pii/S0040402018303685

Vīgante, B., Plotniece, A., Ruciņš, M., Petrova, M., Muhamadejev, R., Pajuste, K., Beļakovs, S., Shermolovich, Y., Sobolev, A. An Efficient Synthesis of Multisubstituted 4-Nitrobuta-1,3-Dien-1-Amines and Application in Cyclisation Reactions. Tetrahedron, 2018, Vol.74, Iss.21, 2596.-2607.lpp. ISSN 0040-4020. Pieejams: doi:10.1016/j.tet.2018.03.075

Publikācijas valoda
English (en)
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