Nickel(II)-Catalyzed Unexpected [3 + 2] Cycloaddition/[3,3]-Rearrangement of N-Vinyl α,β-Unsaturated Nitrones with
Xiao-Ting Qin1, Yue Leng1, Li-Fen Ning1
1Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, China.
Abstract:
A nickel(II)-catalyzed unexpected [3 + 2] cycloaddition/[3,3]-rearrangement cascade reaction was developed for the preparation of various polysubstituted 1-pyrroline-tethered quinazolinones containing three contiguous stereocenters in moderate to good yields with high diastereoselectivity from N-vinyl cinnamaldehyde nitrones and 2-alkynyl quinazolinones. Polysubstituted pyrrolizine-tethered quinazolinones were obtained in good yields when N-vinyl cinnamaldehyde nitrones were replaced by N-vinyl chalcone nitrones. The present method features a broad substrate scope, high [3,3]-rearrangement selectivity and diastereoselectivity, and two substituent bifurcated types of N-heterocycles.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Cycloaddition Reactions: Overview
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...
Nucleophilic Aromatic Substitution: Elimination–Addition
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
