Transition Metal‐Catalyzed C−H Activation/Annulation Approaches to Isoindolo[2,1‐b]isoquinolin‐5(7H)‐ones

Abstract

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 CÀ 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 CÀ H activation/ annulation. It will help researchers to find hidden opportunities and accelerate the discovery of novel transformations based on CÀ H activation/annulation.

Recent Advances in the Synthesis of Rosettacin

“…Compared with all-carbon cycles, heterocycles often own different physical and chemical properties due to the presence of heteroatoms [1][2][3][4][5][6][7]. Thus far, heterocycles are the largest branch of organic compounds.…”

“…In addition, they are not only important in biology and industry but also have great significance in the operation of human society. Their involvement in multiple fields should be given more attention [1][2][3][4]. The main portion of commercial drugs based on mimicking biologically active natural products is heterocycles.…”

“…In the Comprehensive Medicinal Chemistry database, more than 60% of the compounds possess heterocycles [11]. Therefore, researchers continuously design and produce drugs, insecticides, rodenticides and herbicides with better effects based on natural product models [1][2][3][4]. Heterocycles play an important role in biochemical processes and are also the most typical and important organic compounds in living cells [1][2][3][4].…”

Chemical insights into the synthetic chemistry of five-membered saturated heterocycles—a transition metal–catalyzed approach

“…As a result, the structure of drug-like candidates is changing ( Bauer et al, 2021 ), with more emphasis placed on saturated rings such as heterocycles ( Ahmad Khera et al, 2010 ). Further, the combination of saturated heterocycles with aromatic substituents caters for special, attractive screening of sole compounds or lead-like compounds due to the different hidden available binding interactions ( Croft et al, 2019 ; Tang et al, 2023a ).…”

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“…Given the above, advancements in post-Ugi transformations still represent a highly active research field aimed at overcoming bottlenecks in the synthesis of target bioactive heterocycles, natural products, and macrocycles. [9] As part of ongoing interest in this field, [10a] a twostep strategy involving Ugi isocyanide based multicomponent reactions (IMCRs) followed by a Bischler-Napieralski (B-N) heterocyclization directly enabled the synthesis of trisubstituted 5,6-dihydroimidazo[1,2a]pyrimidines [1',5':1,2]-pyrido [3,4-b]indol-2-ium salts (Scheme 1, previous work). [10b] Currently, one of the most popular reactions usually associated with MCRs is the Pictet-Spengler (P-S) ring closure.…”