Recent advances in the use of conjugated nitro or dinitro-1,3-butadienes as building-blocks for the synthesis of heterocycles

• Published in: Tetrahedron letters 2020-09, Vol.61 (36), p.152297, Article 152297
• Main Authors: Petrillo, Giovanni, Benzi, Alice, Bianchi, Lara, Maccagno, Massimo, Pagano, Angela, Tavani, Cinzia, Spinelli, Domenico
• Format: Article
• Language: English
• Subjects: Benzannulation; Cyclization; Dinitrobutadienes; Heterocycles; Nitrobutadienes
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2020.152297

[Display omitted] •Nitro- or dinitro-1,3-butadienes are valuable building blocks in synthesis.•Diverse heterocycles can be prepared from nitro- or dinitro-1,3-butadienes.•Among others, benzannulation protocols can lead to fused heterocycles. The nitrovinyl moiety is surely one of the most reactive fragments in organic chemistry, continuously employed to explore original pathways and reach new targets. The short review herein represents an update on the potentialities in synthesis of conjugated mononitro or dinitro-1,3-butadienes: in such building blocks, the electrophilicity of the nitrovinyl moiety couples and takes advantage from the presence of a second, conjugated, vinyl moiety, most often leading to the eventual formation of diverse and/or diversely-functionalized heterocycles. The review will thus first of all provide chemists with recent, original protocols to such an important class of organic compounds as heterocycles, materials of choice for a lot of practical applications in different fields of human life.