Synthesis of isoindolo[1,2-a]isoquinoline and isoindolo[2,1-a]quinoline derivatives via trifluoroacetic acid-mediated cascade reactions

Synthesis of Multifused Pyrrolo[1,2-a]quinoline Systems by Tandem Aza-Michael–Aldol Reactions and Their Application to Molecular Sensing Studies

“…To further explore the utility of our method, we wanted to examine the reaction in the cycloalkenyl system to get the tetracyclic fused pyrrolo­[1,2- a ]­quinoline which has been found in biologically active natural alkaloids such as jamtinine and hirsutine . These natural product analogues were successfully synthesized using the reductive/aza-Michael/aldol reaction under the optimized reaction condition as described in Table .…”

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

“…Bioactive scaffolds such as nuevamine, jamtine, and hirsutine have been embedded with framework of isoindolo[1,2- a ]isoquinoline as its pharmacophore. 121…”

Transition metal-free advanced synthetic approaches for isoindolinones and their fused analogues

“…10 Herein, we are interested in the synthetic pathways for isoindolinones and their fused analogues from available starting materials that do not contain any isoindolinone scaffolds in the initial step. Although there is a greater number of reports available on transition-metal catalyzed reactions 11 a – g via the reduction of the number of reaction steps to obtain the most available isoindolinone-based structures, transition metal-free protocols 12–53 offer various advantages over transformations involving transition metal catalysts. Transition metal-catalyzed protocols have the following drawbacks: (a) most metals are very sensitive to air and moisture, (b) toxic metals can easily mixed with drainage water during work-up, and (c) the high cost of metal catalysts is another barrier in the pharmaceutical industry.…”

“…The high functional group tolerance is an advantage of this atom-economic transformation. 15 This green protocol underwent cascade cyclization with a variety of o -(substituted ethynyl)benzoic acids 19 and benzyl amines 20 , under the optimum conditions (Scheme 5). A range of alkylamines and aromatic-substituted benzylamines could participate in the reaction to afford hydroxyisoindolinone 21 with excellent yields (70–98%).…”