Hydrophilic Pd-phosphines catalyzed one-pot synthesis of substituted isoquinolines, furopyridines and thienopyridines in aqueous medium

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

“…[172] Again in 2019, Guguloth et al reported the similar protocol as reported by Verma et al [42] towards the synthesis of isoquinolines and other N-heterocycles using a hydrophilic Pd-phosphine catalyst (Scheme 172). [173] Reddy et al have improvised the strategy developed by Grübel et al [128] using Pd-catalyzed 6-exo-trig cyclization of N-(2-halobenzyl)-N-allylamines 295 to furnish C4-substituted tetrahydroisoquinolines 296 (Scheme 173). [174] Sun developed protocols enables to achieve 3,4-dihydroisoquinolones 299 and 299* in excellent yields and enantioselectivity(Scheme 174).…”

“…towards the synthesis of isoquinolines and other N ‐heterocycles using a hydrophilic Pd‐phosphine catalyst (Scheme 172). [173] …”

Alkaline-Metal-Promoted Divergent Synthesis of 1-Aminoisoquinolines and Isoquinolines

“…Particularly, 1-aminosubstituted isoquinolines are the most common with potent biological and pharmacological properties, on which the discovery of drugs such as B-Raf inhibitor, tumor inhibitor (CWJ-082), topoisomerase inhibitor, and antagonist for the human adenosine A3 receptor (VUF8504) is based. Consequently, many synthetic methods have been developed to access isoquinoline scaffolds, including transition-metal-catalyzed benzannulation reactions and sequence Sonogashira coupling/cyclization, while the synthesis of aminated isoquinolines mainly depends on nucleophilic additions/annulation, cascade cyclization of 2-alkylnyl aromatic oximes/nucleophilic additions, C–N cross-coupling reactions and S N Ar reactions of 1-haloisoquinolines with amines …”

NHC-Mediated Stetter-Aldol and Imino-Stetter-Aldol Domino Cyclization to Naphthalen-1(2H)-ones and Isoquinolines

“…In general, derivatives of naphthalen-1­(2 H )-ones are synthesized by an intra/intermolecular Friedel–Crafts cyclization whereas isoquinolines and their derivatives are generally prepared by modified traditional methods such as Pictet–Spengler cyclization, Bischler–Napieralski cyclization/reduction, and Pomeranz–Fritsch–Bobbitt cyclization . However, in spite of significant advances, these methods suffer from limitations such as the use of expensive metal catalysts, special ligands, and/or harsh reaction conditions. Hence, the development of a suitable non-metal-catalyzed mild method for accessing substituted isoquinolines is highly desirable.…”