One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives using new organocatalyst (original) (raw)

One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives in fluoro alcohols

Journal of Fluorine Chemistry, 2009

À [16], in situ generated HCl [17], K 7 [PW 11 CoO 40 ] [18], metal triflates [19], I 2 [20] silica-supported acids [21,22], ceric ammonium nitrate [23], PTSA-SDS [24], tris(pentafluorophenyl)borane [25] and boronic acids [26,27]. These methods, however, suffer from drawbacks such as unsatisfactory yields, acidic or basic catalysts,

FeF3 as a novel catalyst for the synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction

Journal of Fluorine Chemistry, 2012

A facile and highly efficient one-pot synthesis of polyhydroquinoline derivatives is reported via fourcomponent condensation reaction of aldehydes, b-keto compounds, active methylene compounds and ammonium acetate in the presence of FeF 3 as a catalyst in ethanol at 75-80 8C. The method offers several advantages including high yields, short reaction time, simple work-up procedure and catalyst reusability for several runs. The higher catalytic activity of FeF 3 ascribed due to its high acidity, thermal stability and water tolerance. The superiority of use of FeF 3 to the current process is compared with other Lewis acids, Fe-salts, fluoride sources and insights of the origin of the efficiency are discussed.

LaCl3.7H20: An efficient catalyst for one-pot multi-component synthesis of 1,4-polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction

Iranian Chemical Communication, 2017

An efficient one-pot multi component synthesis of 1, 4-Polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction using lanthanum chloride heptahydrate (LaCl3.7H2O) from an aromatic aldehyde, ethyl acetoacetate, dimedone and ammonium acetate as a nitrogen precursor in ethanol at room temperature is described. In the present work, we report lanthanum chloride heptahydrate remarkably non-toxic in nature and ease of handling, we explored the utility of lanthanum chloride heptahydrate as a catalyst for the synthesis of 1, 4polyhydroquinoline derivatives. We newly report p-N, N-dimethylaminocinnamaldehyde and m-chlorobenzaldehyde for the synthesis of 1, 4-Polyhydroquinoline derivatives through unsymmetrical Hantzsch reaction and the products were characterized by IR and 1 HNMR spectroscopic methods.

One-Pot Synthesis of Polyhydroquinoline Derivatives through Organic-Solid-Acid-Catalyzed Hantzsch Condensation Reaction

ChemCatChem, 2017

We report the synthesis of a new microporous copolymer PPN using triphenylamine and ,-dibromo-p-xylene via Friedel-Crafts alkylation process promoted through anhydrous FeCl3 as an oxidising agent and after the sulfonation of PPN we got sulfonated polymer SPPN having high surface acidity with high BET surface area. We have characterized the PPN and SPPN materials thoroughly by using powder XRD, FT IR, 13 C solid state MAS NMR, FE SEM, HR TEM and N2 sorption techniques. This sulfonated material SPPN has been employed as a heterogeneous, reusable and environmentally benign organic solid acid catalyst for the onepot synthesis of biologically important polyhydroquinoline derivatives under microwave irradiation. Scheme 2. Synthesis of PPN and SPPN.

Silica-Supported Alginic Acid-L-Glutamic Acid: An Efficient Heterogeneous Catalyst for Solvent-free Synthesis of 1,8-Dioxohexahydroacridine and Polyhydroquinoline Derivatives

Proceedings of The 18th International Electronic Conference on Synthetic Organic Chemistry, 2014

The classical Hantzsch reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful 1,4-dihydropyridine derivatives. Silica-supported alginic acid-L-glutamic acid (SiO2-AA-L-Glu) under thermal and solvent free conditions is proven to act as a highly efficient catalyst for a one-pot four component reaction of various aldehydes, ammonium acetate, cyclic 1,3-dicarbonyl compounds and ethyl acetoacetate for the synthesis of biologically active substituted Hantzsch 1,8dioxohexahydroacridine and polyhydroquinoline derivatives in excellent yields. The present environmentally benign procedure for the synthesis of 1,4-dihydropyridines is suitable for library synthesis and it will find application in the synthesis of potent biologically active molecules. The process presented here is operationally simple, environmentally benign and has excellent yield with short reaction time and straightforward workup. Furthermore, the catalyst can be recovered conveniently and reused efficiently.

ONE-POT SYNTHESIS OF HANTZSCH ESTERS AND POLYHYDROQUINOLINE DERIVATIVES CATALYZED BY γ-Al 2 O 3 -NANOPARTICLES UNDER SOLVENT-FREE THERMAL CONDITIONS

Revue Roumaine de Chimie

Alumina nanoparticles are used as an effective and reusable catalyst for one-pot synthesis of 1,4-dihydropyridine and polyhydroquinoline derivatives via multicomponent Hantzsch reaction at 90 o C under solvent-free conditions. A broad range of structurally diverse aldehydes were applied successfully, and corresponding products were obtained in high yields without any byproduct. Compared with other methods, satisfactory results are obtained with high yields, short reaction times, and simplicity in the experimental procedure. The catalyst could easily be recycled and reused four times without noticeable decrease in catalytic activity.

Nafion-H®-catalyzed synthesis of polyhydroquinolines via the Hantzsch multicomponent reaction

Monatshefte für Chemie - Chemical Monthly, 2012

A facile and efficient one-pot, four-component synthesis of polyhydroquinoline derivatives via the Hantzsch reaction using Nafion-H Ò as heterogeneous catalyst in PEG 400-water solvent system is described herein. The present methodology offers several advantages such as excellent yields, simple procedure, shorter reaction times, and milder conditions with remarkable recyclability.