Synthesis of Indenopyrazole Frameworks via Cascade C-H Functionalization/[3 + 2] Dipolar Cycloaddition/Aromatization
Min Wu1, Ruiqi Wang2, Fangyuan Chen1
1Guangzhou Municipal and Guangdong Provincial Key Laboratory of Protein Modification and Degradation & Molecular Target and Clinical Pharmacology, State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, Guangdong 511436, China.
Abstract:
The redox-neutral Ir(III)- or Ru(II)-catalyzed C-H couplings of azomethine imines with α,α-difluoromethylene alkynes have been realized, leading to the efficient synthesis of indenopyrazole frameworks via a tandem C-H functionalization/[3 + 2] dipolar cycloaddition/ring-opening aromatization rearrangement process, in which the generated fluoroallene species was involved as the dipolarophile via a selective β-F elimination process. Subsequent biological evaluation revealed that these synthesized indenopyrazoles could serve as interesting cytotoxic agents for further development.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Cycloaddition Reactions: MO Requirements for Thermal Activation
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
