Pyridine-Catalyzed Chemoselective Four-Component Cascade Reaction of Aromatic Aldehydes, Malononitrile/Cyanoacetates, MBH Carbonates, and Alcohols
An efficient pyridine-catalyzed chemoselective four-component cascade reaction of aromatic aldehydes, malononitrile/cyanoacetates, Morita-Baylis-Hillman (MBH) carbonates, and alcohols has been established. This one-pot reaction progressed in an unusual reaction with solvent participation via a Knoevenagel condensation/oxa-Michael addition/S<sub>N</sub>2' substitution sequence. This method allowed for facile access to an array of functionalized chain alkylbenzenes and dihydroquinolinones bearing one all-carbon quaternary center in moderate to excellent yields. It is worth noting that the configuration of the all-carbon quaternary center could be modulated by changing only the electron-withdrawing groups via a tandem reduction/cyclization reaction.
Authors
- Boning Li (ORCID: https://orcid.org/0009-0008-1727-5242)
- Nengzhong Wang (ORCID: https://orcid.org/0000-0003-1690-7611)
- Hui Qin Yao (ORCID: https://orcid.org/0000-0002-4450-8602)
- Yi Li (ORCID: https://orcid.org/0000-0002-4236-262X)
- Nianyu Huang (ORCID: https://orcid.org/0000-0003-4483-160X)
- Dan Xu (ORCID: https://orcid.org/0009-0006-1798-1716)
- Xianfei Hu
Institutions
- China Three Gorges University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-03
- DOI
- https://doi.org/10.1021/acs.orglett.4c02612
- Citations
- 12
- Primary Topic
- Multicomponent Synthesis of Heterocycles
- Type
- article
- Field-Weighted Citation Impact
- 3.00
Funders
- Hubei Provincial Department of Education
- Natural Science Foundation of Yichang City
- National Natural Science Foundation of China
- Natural Science Foundation of Hebei Province
- Higher Education Discipline Innovation Project