Dipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, Via Dodecaneso 31, 16146 Genova, Italy.
Dipartimento di Biotecnologie, Chimica e Farmacia, Università di Siena, Via A. Moro, 53100 Siena, Italy.
Molecules. 2022 May 14;27(10):3147. doi: 10.3390/molecules27103147.
Nitrostilbenes characterized by two different or differently substituted aryl moieties can be obtained from the initial ring-opening of 3-nitrobenzo[]thiophene with amines. Such versatile building blocks couple the well-recognized double electrophilic reactivity of the nitrovinyl moiety (addition to the double bond, followed by, e.g., intramolecular replacement of the nitro group) with the possibility to exploit a conjugated system of double bonds within an electrocyclization process. Herein, nitrostilbenes are reacted with different aromatic enols provided by a double (carbon and oxygen) nucleophilicity, leading to novel, interesting naphthodihydrofurans. From these, as a viable application, aromatization and electrocyclization lead in turn to valuable polycondensed, fully aromatic -heterocycles.
硝基二苯乙烯由两个不同或不同取代的芳基部分组成，可以通过 3-硝基苯并噻吩与胺的初始开环得到。这种多功能的构建块结合了硝基乙烯基部分（加成到双键上，然后例如，硝基基团的分子内取代）的公认的双重亲电性，以及在电环化过程中利用双键共轭体系的可能性。在此，硝基二苯乙烯与不同的芳香烯醇反应，这些烯醇由双重（碳和氧）亲核性提供，生成了新颖有趣的萘并二氢呋喃。从这些化合物中，作为一种可行的应用，芳构化和电环化依次生成有价值的缩合、全芳香杂环。
