Nickel nanoparticle-catalyzed facile and efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

“…For example, chloroquine (46) has been used for its antimalarial activity for more than 60 years; [56][57][58] bedaquiline (47), an inhibitor of the mycobacterial ATP synthase, has been approved to treat multi-drug resistant tuberculosis, [59] and cabozantinib (48), a multitargeted receptor tyrosine kinase inhibitor, showed effective anticancer activity and has been marketed for the treatment of medullary thyroid cancer ( Figure 4) [60]. Therefore, in the last decade, several new synthetic routes to quinoline derivatives under MW-irradiation have been reported [61][62][63][64][65][66]. Kulkarni et al [61] described a solid acid-catalyzed synthesis of substituted quinolines via a MW-assisted three-component domino reaction between anilines, aldehydes and terminal aryl alkynes.…”

“…The combination of solid acid catalysis, multicomponent domino reaction approach and microwave irradiation provided the quinolones 52 in excellent selectivities and short reaction times (Scheme 10). Therefore, in the last decade, several new synthetic routes to quinoline derivatives under MW-irradiation have been reported [61][62][63][64][65][66]. Kulkarni et al [61] described a solid acid-catalyzed synthesis of substituted quinolines via a MW-assisted three-component domino reaction between anilines, aldehydes and terminal aryl alkynes.…”

“…This synthetic pathway showed a significant acceleration of the reaction under MW (10 min) compared to the conventional heating (4 h), and leads to the expected tetrahydrobenzo [ The use of nickel nanoparticles as a heterogeneous catalyst for the synthesis of polyhydroquinoline derivatives 74 via solvent-free Hantzsch condensation was described by Sapkal et al [66]. In this work, a one-pot four component reaction involving aromatic aldehydes 71, dimedone (72), ethyl acetoacetate (73) and ammonium acetate led to polyhydroquinoline derivatives in excellent yields after short reaction times (Scheme 16).…”

1-Butyl-3-Methyl Imidazolium Hydrogen Sulphate Promoted One-Pot Three-Component Synthesis of Amidoalkyl Naphthols

“…15 Very recently, we have reported the convenient synthesis of polyhydroquinolines and 2,4,5-triarylimidazole derivatives via multicomponent condensation reaction. 16,17 Due to the environmental concerns, the use of benign solvents as an alternative to volatile organic solvents and are of much interest to organic chemist. The use of ionic liquid as a reaction media and catalyst can offer a solution to solvent emission and catalyst recycle problems.…”

Carbon-Based Solid Acid Catalyzed Synthesis of Polyhydroquinoline Derivatives via Hantzsch Reaction Under Solvent-Free Conditions

“…, and nickel nano particle 23 . However, most of these methodologies suffer from disadvantages such as unsatisfactory yields, toxic organic solvents, harsh reaction conditions, long reaction times and the use of relatively expensive reagents.…”