Isoquinolone Syntheses by Annulation Protocols

Abstract

Isoquinolones (isoquinolin-1(2H)-ones) are one of the important nitrogen-heterocyclic compounds having versatile biological and physiological activities, and their synthetic methods have been recently developed greatly. This short review illustrates the significant advances in the construction of isoquinolone ring with atom- and step-economy, focusing on the intermolecular annulation protocols and intramolecular cyclization in the presence of a variety of catalyst systems. The syntheses of isoquinolone-fused rings are also included.

An asymmetric metal-templated route to amino acids with an isoquinolone coreviaa Rh(iii)-catalyzed coupling of aryl hydroxamates with chiral propargylglycine Ni(ii) complexes

“…Among the different strategies to synthesize isoquinolones, 4,5 a Rh( iii )-catalyzed C–H activation/annulation of various readily available aryl hydroxamates with alkynes is one of the most efficient and straightforward approaches. 6,7 In particular, this reaction proved to be a key step in the total synthesis of natural products, such as rosettacin and nauclefine.…”

Dess–Martin Periodinane-Mediated Oxidative Coupling Reaction of Isoquinoline with Benzyl Bromide

“…Isoquinoline is an essential structural unit in pharmaceutical molecules and naturally occurring alkaloids [ 1 , 2 , 3 ]. In particular, isoquinolinones and their derivatives are the critical moiety of many pharmaceuticals [ 4 , 5 ]. As a member of the isoquinoline alkaloid family, isoquinolinones have exhibited a wide range of structural diversity and biological activity [ 6 , 7 ], and gliquidone is used as a commercial drug to treat diabetes ( Figure 1 , I ) [ 8 ].…”

Synthesis of Fused Tetracyclic Compounds via Oxidative Annulation: Access to Copper-Catalyzed Indolo[1,2-a]quinolines and to Ruthenium-Catalyzed Isoquinolin-1[2H]-ones

“…To synthetize such molecules, the oxidative addition of benzamides with alkynes has drawn a lot of attention as it does not require prefunctionalization of the substrates while affording multi-substituted adducts . In particular, alkynyl-tethered amides are well-recognized as versatile building blocks towards N -containing cyclic architectures and proved to be efficient in intramolecular oxidative annulations, leading to isoquinolinone fused tricyclic compounds .…”