One-pot and regioselective synthesis of functionalized γ-lactams via a metal-free sequential Ugi 4CR/Intramolecular 5-exo-dig cyclization reaction. Issue 34 (21st August 2020)

• Record Type: Journal Article
• Authors: Yan, Yan-Mei; Wang, Meng-Liang; Liu, Yu-Long; He, Ying-Chun
• Is Part Of: Tetrahedron. Volume 76:Issue 34(2020)
• Publication Date: 2020-08-21
• Subjects: γ-lactam -- Regioselective -- Metal-free -- Propenoic acid -- Ugi reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131389
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A new one-pot and regioselective synthesis of functionalized γ -lactams by a metal-free Ugi 4CR/intramolecular 5- exo - dig cyclization sequence under mild conditions has been developed. The reaction of propenoic acids, aldehydes, amines, and isocyanides produced γ -lactams regioselectively in 72–89% yields via sequential Ugi 4CR/intramolecular 5- exo - dig cyclization reaction in the presence of Cs2 CO3 . Graphical abstract: To create your abstract, type over the instructions in the template box below. Fonts or abstract dimensions should not be changed or altered. Image 1 Highlights: We provided a new one-pot and regioselective synthesis of functionalized γ-lactams by a metal-free Ugi 4CR/intramolecular 5- exo-dig cyclization sequence. There is no report previously on the sequential Ugi 4CR/intramolecular cyclization to prepare γ -lactams regioselectively by using propenoic acid as acid component in the Ugi reaction. Owing to the high atom efficiency, the good yields, the mild reaction conditions, metal-free and the easily available starting materials, the efficient synthesis will make it useful in synthetic and medicinal chemistry. .