Substituted Isocoumarins: An Assemble of Synthetic Strategies Towards 3‐Substituted and 3,4‐Disubstituted Isocoumarins

Abstract

The versatility of isocoumarin frameworks offers the privilege to access many pharmacological targets. This unique heterocycle core present in many natural products and complex organic molecules contribute to medicinal chemistry as anti-cancer, anti-inflammatory and immunomodulatory agents. The attractive properties exhibited by its analogues urged the scientists to explore their synthetic analogues. In regard to the myriads of synthetic methodologies, we have compiled a review update covering all the articles that have been published towards the synthesis of 3substituted and 3,4-disubstituted isocoumarins. Additionally, we have also highlighted a systematic survey of catalytic methods for their synthesis along with their scope towards diverse functionalizations and plausible mechanistic aspects.

[2.2]Benzoindenophane‐Based Chiral Indenyl Ligands: Design, Synthesis, and Applications in Asymmetric C−H Activation

“…Since the pioneering work by Miura, Satoh and co‐workers in 2007, [18] synthesis of isocoumarins through transition metal catalyzed C(sp 2 )−H activation/oxidative coupling of benzoic acids with internal alkynes has attracted wide interest and been intensively studied [19] . However, the asymmetric catalysis involving this elegant chemistry has never been reported.…”

“…Since the pioneering work by Miura, Satoh and co-workers in 2007, [18] synthesis of isocoumarins through transition metal catalyzed C(sp 2 )À H activation/oxidative coupling of benzoic acids with internal alkynes has attracted wide interest and been intensively studied. [19] However, the asymmetric catalysis involving this elegant chemistry has never been reported. With this in mind and also to further explore the application of our newly developed chiral Ind x Rh catalysts, we designed and investigated the asymmetric CÀ H activation reaction of benzoic acid 15 with alkyne 16, which would give axially chiral isocoumarin 17.…”

Novel Metal-Free Synthesis of 3-Substituted Isocoumarins and Evaluation of Their Fluorescence Properties for Potential Applications

“…Isocoumarins, especially 3-substituted isocoumarins, constitute an important class of heterocyclic scaffolds owing to their diverse biological activities, including antibacterial [ 1 ], enzyme inhibition [ 2 ], antifungal [ 3 ], and antipheromonal effects [ 4 ], as well as anticancer [ 5 ] and anti-HIV properties [ 6 ]. Additionally, there are important applications in organic light-emitting materials [ 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. Given their great importance, substantial efforts have been dedicated to developing new synthetic methods for the preparation of isocoumarins, driven by their potential applications ( Scheme 1 ) [ 14 ].…”