DBU-mediated [4 + 2] annulations of donor–acceptor cyclopropanes with 3-aryl-2-cyanoacrylates for the synthesis of fully substituted anilines
| Autor: | Cunde Wang, Siran Qian, Zhenjie Su, Jiaming Liu |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Annulation
Nucleophilic addition 010405 organic chemistry Stereochemistry General Chemical Engineering Aryl Aromatization Regioselectivity General Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Intramolecular force Michael reaction |
| Zdroj: | RSC Advances. 7:38342-38349 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c7ra07230a |
| Popis: | A facile synthesis of fully substituted anilines by the DBU-mediated [4 + 2] annulation of donor–acceptor 1,1-dicyano-cyclopropanes with 3-aryl-2-cyanoacrylate has been developed. This reaction involves a highly efficient multiple domino sequence consisting of ring opening of donor–acceptor cyclopropanes, regioselective intermolecular Michael addition, intramolecular nucleophilic addition and aromatization as key unit steps. This transformation provides a straightforward synthetic protocol for constructing fully substituted aniline derivatives. The structure of two typical products was confirmed by X-ray crystallography. |
| Databáze: | OpenAIRE |
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