Base-Mediated Chemodivergent [4 + 1] and [2 + 1] Cycloadditions of N-Alkylpyridiniums and Enones DOI

Dehao Duan,

Yifei Wei,

Tianyou Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 11959 - 11974

Published: Aug. 27, 2024

Divergent synthesis of structurally different products from the same kinds starting materials is highly synthetically useful but very challenging. Herein, we reported a base-mediated chemodivergent [4 + 1] and [2 cycloaddition N-alkylpyridinium enone under mild conditions, leading to furan-fused bicycles with high diastereoselectivity spirobicycles, respectively, moderate yields. N-Alkylpyridinium salts were modular nucleophilic transfer reagents C1 synthons, which underwent tandem Michael addition α,β-unsaturated ketones cyclization base conditions. Late-stage derivatization 4-propyldicyclohexylanone an important industrial raw liquid crystal display (LCD) screens was realized. In vitro, compound 3f exhibited good activities against human colon cancer cells (HCT116) IC50 values in 9.82 ± 0.27 μM. Further biological evaluations investigated mechanism effective inhibition cell growth, including apoptosis ratio detection, cycle analysis, migration capacity HCT116 cells. effect studies, complex increased percentage apoptotic 26.8% (15 μM).

Language: Английский

Palladium-Catalyzed (4 + 1) Annulation of 4-Vinylbenzodioxinones with Sulfur Ylides: Diastereoselective Synthesis of Dihydrobenzofuran Derivatives DOI
Yi Tang, Xiaojing Sun,

Yu Tan

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8951 - 8959

Published: May 30, 2024

Palladium-catalyzed (4 + 1) annulation of 4-vinylbenzodioxinones with sulfur ylides has been developed to afford various dihydrobenzofuran derivatives in moderate high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating application potential current organic synthesis.

Language: Английский

Citations

1
Pd-Catalyzed Sequential Intramolecular Annulation/ Intermolecular [3+2] Cycloaddition of 5-Allenyloxazolidine-2,4-diones with Dipoles: Synthesis of Spiroheterocycles DOI
Yujie Dong, Jun Liu,

Rongjin Ning

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(76), P. 10516 - 10519

Published: Jan. 1, 2024

Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various reacted 1,3-dipoles such as nitrile

Language: Английский

Citations

0
Base-Mediated Chemodivergent [4 + 1] and [2 + 1] Cycloadditions of N-Alkylpyridiniums and Enones DOI

Dehao Duan,

Yifei Wei,

Tianyou Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 11959 - 11974

Published: Aug. 27, 2024

Divergent synthesis of structurally different products from the same kinds starting materials is highly synthetically useful but very challenging. Herein, we reported a base-mediated chemodivergent [4 + 1] and [2 cycloaddition N-alkylpyridinium enone under mild conditions, leading to furan-fused bicycles with high diastereoselectivity spirobicycles, respectively, moderate yields. N-Alkylpyridinium salts were modular nucleophilic transfer reagents C1 synthons, which underwent tandem Michael addition α,β-unsaturated ketones cyclization base conditions. Late-stage derivatization 4-propyldicyclohexylanone an important industrial raw liquid crystal display (LCD) screens was realized. In vitro, compound 3f exhibited good activities against human colon cancer cells (HCT116) IC50 values in 9.82 ± 0.27 μM. Further biological evaluations investigated mechanism effective inhibition cell growth, including apoptosis ratio detection, cycle analysis, migration capacity HCT116 cells. effect studies, complex increased percentage apoptotic 26.8% (15 μM).

Language: Английский

Citations

0