CuCl2-catalyzed inexpensive, faster and ligand/additive free synthesis of isoquinolin-1(2H)-one derivatives via the coupling–cyclization strategy: Evaluation of a new class of compounds as potential PDE4 inhibitors

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

“…Thirupataiah et al established an additive free approach towards synthesising isoquinolinone derivative 35 (Scheme 6). 50 The protected aminosulfonyl compound 32 gets activated by a copper catalyst and functionalized with 2-iodobenzamides 33 to achieve the amidate intermediate 34 . Cascade cyclization of intermediate 34 involving a 6- endo-dig results in 3-substituted isoquinoline scaffolds 35 .…”

“…49 A cascade asymmetric Heck/Suzuki reaction of 2-iodobenzamide 27 with phenyl boronic acid pinacol ester 28, catalysed by Pd/Xu-Phos, affords 4,4-disubstituted dihydroisoquinolinone 30. 50 The protected aminosulfonyl compound 32 gets activated by a copper catalyst and functionalized with 2-iodobenzamides 33 to achieve the amidate intermediate 34.…”

Recent Advances in the 3 d‐Transition‐Metal‐Catalyzed Synthesis of Isoquinolines and its Derivatives

“…Mechanistically, with the support of K Benzimidazo[2,1-a]isoquinolin-6(5H)-ones 130 were synthesized from cyclobutanone oxime esters 128 and N-methacryloyl-2-phenylbenzimidazoles 129 via Cu-catalyzed domino ring-opening/cyclization reactions by Wei and coworkers (Scheme 47). [81] The domino reaction has been performed in a biomassderived solvent 2-methyltetrahydrofuran ( 2 In 2021, Pal and coworkers [82] synthesized a series of isoquinolin-( 1 Ultrasound-assisted synthesis of isoquinolinones 136 from easily available precursors, 2-iodobenzamide 134 and ketones 135 via a CuI-catalyzed sequential coupling reaction, followed by cyclization in one-pot has been reported by Pal and coworkers (Scheme 49). [83] Various isoquinolinones 136 contain-ing different functional groups were synthesized in yields up to 93%.…”

“…In 2021, Pal and coworkers [82] synthesized a series of isoquinolin‐(1)2 H ‐ones 133 bearing aminosulphonyl moiety via a CuCl 2 ‐mediated coupling/cyclization reaction of 2‐iodobenzamides 131 with alkynes 132 in a chemo‐/regio‐selective manner (Scheme 48). They conducted anti‐inflammatory activities of the synthesized compounds and some of them displayed good inhibitory activity towards PDE4 (phosphodiesterase 4).…”

Ultrasound Assisted α‐Arylation of Ketones: A Rapid Access to Isoquinolinone Derivatives

“…[25,26] Several metal catalyzed reactions have been reported to be accelerated by ultrasound irradiation that was thought to be because of synergy between catalysis and ultrasound, implosion of cavitation bubbles on the catalytic surface thereby activating the catalyst etc. [26] Due to our interest in this area [27,28] herein, we report ultrasound assisted αarylation of ketones (2) using 2-iodobenzamide (1) as the aryl halide in the presence of CuI affording a rapid and greener access to various isoquinolin-1(2H)-one derivatives (3, Scheme 1).…”