Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 19, 2024

Abstract A novel bismuth(III) trifluoro‐methanesulfonate‐catalyzed and environmentally benign synthetic strategy for the construction of a wide range structurally diverse, sophisticated [5,6,5]‐oxygen‐containing tricyclic frameworks with easy‐to handle propargylic alcohols 2‐allylphenols as substrates in presence Bi(OTf) 3 AgOTf is described. This Lewis acid catalyzed [3+2] annulation protocol, which tolerates great deal functional groups, proceeds through sequential Meyer‐Schuster rearrangement, nucleophilic substitution, 5‐ exo ‐trig cyclization, endo proton exchange sequences, affording versatile approach accessing oxygen‐containing skeletons moderate‐to‐excellent yields. In addition, most obtained compounds exhibited anti‐tumor activities against three types human cancer cell lines vitro , including Caco‐2 colon cells, MCF‐7 breast Hepg‐2 liver cells.

Language: Английский

Organocatalytic Asymmetric [3 + 2] Cyclization: Enantioselective Synthesis of α-Indolyl Pyrrolo[1,2-a]indole Scaffolds

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 26, 2024

A novel asymmetric [3 + 2] cyclization of α-indolyl propargylic alcohols with 3-alkyl-1H-indoles via chiral phosphoric acid catalysis has been established. This strategy allowed the synthesis pyrrolo[1,2-a]indole derivatives high yields (up to 91%) and excellent enantioselectivities 99% ee), facilitating both reaction activity enantioselectivity by using solvent CH

Language: Английский