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An efficient synthesis of multisubstituted 4-nitrobuta-1,3-dien-1-amines and application in cyclisation reactions
Authors:Brigita Vigante  Aiva Plotniece  Martins Rucins  Marina Petrova  Ruslan Muhamadejev  Karlis Pajuste  Sergey Belyakov  Yuriy G. Shermolovich  Arkadij Sobolev
Affiliation:1. Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, Riga, LV-1006, Latvia;2. Institute of Organic Chemistry NAS of Ukraine, Murmanska Str. 5, 02660, Kyiv, Ukraine
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.
Keywords:4-Nitrobuta-1,3-dien-1-amine  Nitrodienamine  3-Aminocrotonate  Nitroacetaldehyde potassium salt  Cyclisation reaction  Dihydropyridines
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