DBU-mediated [4+2] annulations of donoracceptor cyclopropanes with 3-aryl-2-cyanoacrylates for the synthesis of fully substituted anilines

作者：Liu, Jiaming; Qian, Siran; Su, Zhenjie; Wang, Cunde^*

来源：RSC Advances, 2017, 7(61): 38342-38349.

DOI：10.1039/c7ra07230a

• DONOR-ACCEPTOR CYCLOPROPANES
• 1-CYANOCYCLOPROPANE 1-ESTERS
• POLYSUBSTITUTED BENZENES
• STRAIGHTFORWARD APPROACH
• CARBENE COMPLEXES
• BENZOIC-ACID
• RING
• BENZANNULATION
• CONSTRUCTION
• STRATEGY

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.

• 出版日期2017
• 单位扬州大学