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

Author:
Vigante, Brigita, Plotniece, Aiva, Rucins, Martins, Petrova, Marina, Muhamadejev, Ruslan, Pajuste, Karlis, Belyakov, Sergey, Shermolovich, Yuriy G., Sobolev, Arkadij
Source:
Tetrahedron 2018 v.74 no.21 pp. 2596-2607
ISSN:
0040-4020
Subject:
aldehydes, chemical structure, cyclization reactions, potassium, protocols
Abstract:
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.
Agid:
6289834