Heteroaromatic Aldehydes with Unprecedented Catalytic Performance in Selective Radical Reactions: Synthesis of α‐Aminophosphonate Scaffolds

Abstract

Heterocyclic compounds have gained immense importance because of their low resonance energy and strong hydrogen-bonding abilities, which provide good catalytic potential in a variety of organic transformations. Herein an unexpected metal-free catalytic performance of heteroaromatic aldehydes has been reported. Accordingly, a unique method for the synthesis of new scaffolds of peptidomimetic compounds, α-aminophosphonates has been developed, which was difficult using previous methods. The aerobic auto-oxidation of heteroaromatic aldehydes acts as a driving force for the coupling of aromatic N-benzylamines and hydrophosphoryl compounds according to a one-pot, metal-and solvent-free procedure. Heteroaromatic aldehydes, in addition to their individual ability to promote selective radical reactions through the auto-oxidation process, can provide hydrogen bonding frameworks at different stages of the reaction and thereby change the reaction pathways and induce new activities and selectivities, which unveiled their other important catalytic features. We believe that this highlights the catalytic potential of heteroaromatic aldehydes, which may offer an opportunity to change the traditional harsh conditions necessary to generate alkyl radicals.[a] Dr. reaction, as monitored by TLC, the reaction mixture was allowed to cool at room temperature. The mixture was then extracted with ethyl acetate three times and dried over MgSO 4 , filtered, and concentrated under reduced pressure. 4 5 6 7 8

Green-inspired synthetic drives for organophosphorus compounds under solvent-free conditions

“…Recently, Aghahosseini et al developed, for the first time, a selective radical reaction, promoted via the auto-oxidation of quinoline-4-carbaldehyde as an effective organocatalyst in the synthesis of αaminophosphonates from a dialkyl phosphite and two molecules of the same N-benzylamine upon heating the reaction mixture in the presence of air (Scheme 12). 99 Interestingly, this is a new version of the Kabachink-Fields reaction that avoids the use of carbonyl compound(s) as one component of this three-component reaction. Instead, the heteroaromatic aldehyde generates a stable acyl radical out of its aerobic autooxidation.…”

Green and efficient synthesis of 1H‐indazolo[1,2‐b] phthalazine‐1,6,11(13H)‐triones using ZrO(NO3)2.2H2O as a novel catalyst and theoretical study of synthesized compounds

“…As MCRs are one‐pot reactions, they are easier to carry out than multistep syntheses. In the last decade, the significance of MCRs for drug discovery has been identified and significant attempts by both academic and industrial researchers have been made, particularly toward the planning and extension of multicomponent proceedings for the production of libraries of heterocyclic compounds . The synthesis of nitrogen‐containing heterocyclic compounds has drawn a considerable amount of attention .…”

Innovational combination of hetero-bifunctional N-PEG quinoline scaffolds derivatives with improved anticancer activity against breast and colon cancer cell lines and P-glycoprotein, cytochrome p450 enzyme activity prediction

“…It was evident that the higher the molecular weight of the starting PEG, the more difficult it was for the isolation of monosubstituted PEG from the reacted mixture. This is because there was no sharp difference between monosubstituted, disubstituted, and raw PEGs in the chemical and physical properties [20][21][22].Heterocyclic mixes have increased gigantic significance as a result of their low reverberation vitality and solid hydrogen-bonding capacities [23]. A recent investigation reported the fruitful synthesis of new heterocyclic-like ester and amide under water as a solvent and the surface of silica-coated CoFe 2 O 4 magnetic nanoparticles for the synthesis of 3-pyrrolin-2-ones [24], as well as for the preparation of 2-amino-4,6-diarylnicotinonitrile under microwave irradiation [25].…”