Synthesis of diverse 2, 3, 4, 5-tetrahydro-1H-azepine derivatives via sequential Knoevenagel reaction and Michael addition of tertiary enamide. (22nd June 2021)

• Record Type: Journal Article
• Authors: Yang, Hanlin; Ning, Zhipeng; Wang, Shiyu; Li, Jiazhu; Wang, Zu-Li; Wang, Wei-Li; Xu, Xin-Ming
• Is Part Of: Tetrahedron letters. Volume 74(2021)
• Publication Date: 2021-06-22
• Subjects: Tertiary enamide -- Azepines -- Knoevenagel reaction -- Michael addition -- N-heterocyclic compound; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153174
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: This protocol underwent the sequential Knoevenagel reaction and Michael addition. The preparation of azepine derivatives containing a quaternary carbon center. High efficiency and mild reaction conditions. Abstract: An exquisite and practical access to construct seven-membered N -heterocyclic rings was established under mild conditions. Tertiary enamides underwent successively Knoevenagel reaction with different active methylene compounds and intramolecular Michael addition under the sequential catalysis of proline and AlCl3 to afford diverse 2, 3, 4, 5-tetrahydro-1 H -azepine derivatives in high yields. The resulting products contained multiple reactive sites and could be converted into other valuable N -heterocyclic compounds.