The isoindolo[2,1-b]isoquinolin-5(7H)-one scaffold is widely present in lots of bioactive natural products. Diverse types of strategies have been developed to construct this scaffold. Recently, transition metal-catalyzed C-H activation/annulation is emerging as a powerful and straightforward method to construct diverse polyheterocycles with high atom- and step-economy. It also has been employed for the synthesis of the isoindolo[2,1-b]isoquinolin-5(7H)-one scaffold. This review provides an introduction to recent advances for the preparation of isoindolo[2,1-b]isoquinolin-5(7H)-ones by using transition metal-catalyzed C-H activation/annulation. It will help researchers to find hidden opportunities and accelerate the discovery of novel transformations based on C-H activation/annulation.
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http://dx.doi.org/10.1002/tcr.202200255 | DOI Listing |
Chem Asian J
December 2024
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, Tamilnadu, India.
We disclosed an efficient protocol for regioselective C6 C-H/N-H activation/annulation reaction of indole-7-carboxamides with alkynes to synthesize highly substituted pyrrolo[3,2-h]isoquinolin-9-one derivatives. Under optimized reaction conditions, electron-deficient and electron-rich internal alkynes reacted efficiently with various indole-7-carboxamides to deliver desired products in good to excellent yields. The synthetic utility of the product is demonstrated by its selective oxidation to the corresponding isatin derivative.
View Article and Find Full Text PDFOrg Lett
December 2024
Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu, China.
Chem Commun (Camb)
October 2024
Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Göttingen, 37077, Göttingen, Germany.
Alkyne annulation represents a versatile and powerful strategy for the assembly of structurally complex compounds. Recent advances successfully enabled electrocatalytic alkyne annulations, significantly expanding the potential applications of this promising technique towards sustainable synthesis. The metallaelectro-catalyzed C-H activation/annulation stands out as a highly efficient approach that leverages electricity, combining the benefits of electrosynthesis with the power of transition-metal catalyzed C-H activation.
View Article and Find Full Text PDFNat Commun
September 2024
Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, People's Republic of China.
Acenaphthylene-containing polycyclic aromatic hydrocarbons (AN-PAHs) are noteworthy structural motifs for organic functional materials due to their non-alternant electronic structure, which increases electron affinity. However, the synthesis of AN-PAHs has traditionally required multiple sequential synthetic steps, limiting structural diversity. Herein, we present a tandem C-H penta- and hexaannulation reaction of aryl alkyl ketone with acetylenedicarboxylate.
View Article and Find Full Text PDFJ Org Chem
October 2024
Guangxi Key Laboratory of Electrochemical and Magneto-Chemical Function Materia, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China.
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