An efficient synthesis of multisubstituted 4-nitrobuta-1, 3-dien-1-amines and application in cyclisation reactions. Issue 21 (24th May 2018)

• Record Type: Journal Article
• Authors: Vigante, Brigita; Plotniece, Aiva; Rucins, Martins; Petrova, Marina; Muhamadejev, Ruslan; Pajuste, Karlis; Belyakov, Sergey; Shermolovich, Yuriy G.; Sobolev, Arkadij
• Is Part Of: Tetrahedron. Volume 74:Issue 21(2018)
• Page Start: 2596
• Page End: 2607
• Publication Date: 2018-05-24
• Subjects: 4-Nitrobuta-1, 3-dien-1-amine -- Nitrodienamine -- 3-Aminocrotonate -- Nitroacetaldehyde potassium salt -- Cyclisation reaction -- Dihydropyridines; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.03.075
• Languages: English
• ISSNs: 0040-4020

Abstract

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. Graphical abstract: