A new process has been developed for the selective construction of 2,6-disubstituted, 2,4,6-trisubstituted, and 3,5-disubstituted pyridines based on catabolism reconstruction behaviors amino acids. Molecular iodine was used as a tandem catalyst to trigger decarboxylation–deamination acids promote subsequent formation pyridine products.

A highly efficient I2/Cu(NO3)2·3H2O-mediated triple C(sp3)–H functionalization reaction for the synthesis of 2,4,5-trisubstituted furans from aryl methyl ketones and rongalite by employing as a C1 unit has been developed. This method allows rapid access to (2-acyl-4-methylthio-5-aryl) furans. Preliminary mechanistic studies indicate that in situ generated dimethyl(phenacyl)-sulfonium iodine HCHO were probably key intermediates this transformation.

An efficient I₂–DMSO reagent system-mediated multicomponent reaction strategy for the synthesis of C3-sulfenylated chromones from <italic>o</italic>-hydroxyaryl methyl ketones, rongalite, and dimethyl sulfoxide has been developed.

A highly efficient rongalite-mediated three-component radical annulation reaction to furnish fully substituted pyrazoles from aryldiazonium salts and α,β-unsaturated aldehydes or ketones under metal- oxidant-free conditions at room temperature has been developed. In this transformation, served as the precursor of both aryl hydrazine units. Mechanistic investigations indicated that rongalite could act a initiator reducing reagent simultaneously in reaction.

A novel mechanoredox-enabled synthesis of aromatic and aliphatic isothiocyanates from primary amines carbon disulfide under ball milling conditions using a piezoelectric material (BaTiO3) as the redox catalyst has been developed. This method displays several features, such short reaction time, operational simplicity, room temperature air conditions, minimal solvent, broad substrate scope, recyclable cheap catalyst. Preliminary mechanistic studies revealed that highly polarized acted...

A highly para-selective C–C bond coupling is presented between phenols C(sp2) and aryl methyl ketones C(sp3), which enables the direct construction of 4-hydroxybenzil derivatives. This practical method exhibits a broad substrate scope large-scale applicability represents general gateway to hydroxybenzil natural product family. Mechanistic investigations indicated that combination HI with DMSO realized oxidative carbonylation ketones, while boric acid acted as dual-functional relay reagent...

A novel synthesis strategy of <italic>N</italic>-aminosulfonamides has been reported which uses rongalite as a radical initiator, SO₂ surrogate and reducing reagent simultaneously.

A practicable quinoline synthesis from aniline and two amino acids was developed for generating a wide range of quinolines with high efficiency diversity. Thus, it facilitated the creations pharmaceutical derivatives, photochemical active compounds, challenging scaffolds. The concept using as heterocyclic precursors has been raised first time. Mechanistic studies revealed that I2 enabled decarboxylation, oxidative deamination, selective reconstruction new C-N C-C bonds processes.

This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application the one-pot total synthesis natural products. method featured stimulating example activating in one pot as multi-carbon building blocks for transformation into final targets which are equipped acid side chain backbones.

The one-pot total synthesis of evodiamine and its analogues is achieved using a three-component reaction. Through continuous biscyclization, various readily available substrates with good functional group tolerance were easily incorporated into biologically active quinazolinocarboline backbones. use triethoxymethane as cosolvent was crucial for this quick straightforward transformation.

Abstract The development of concise, sustainable, and cost‐effective synthesis aryltetralin lignans, bearing either a fused lactone or cyclic ether, is significant medicinal importance. Reported that in the presence Fukuzumi's acridinium salt under blue LED irradiation, functionalized dicinnamyl ether derivatives are converted into lignans with concurrent generation three stereocenters good to high yields up 20:1 diastereoselectivity. Oxidation an alkene radical cation key success this...

Concise synthesis of functionalized quinolines has received continuous research attention owing to the biological importance and synthetic potential bicyclic N-heterocycles. However, routes 2,4-unsubstituted alkyl quinoline-3-carboxylate scaffold, which is an important motif in drug design, remain surprisingly limited, with modular protocols that proceed from readily available materials being even more so. We herein report acidic I2-DMSO system converts aspartates anilines into...

The increasing importance of enzyme mimics in organic synthesis inspired us to design a novel biomimetic β-carboline alkaloids directly from tryptophan and second amino acid. This one-pot protocol utilizes abundant readily available starting materials thus presents green user-friendly alternative conventional methods that rely on stepwise synthesis. Driven by molecular iodine TFA, decarboxylation, deamination, Pictet–Spengler reaction, oxidation reactions proceeded sequentially, transforming...

An unexpected rearrangement aromatization of benzo[c]oxepine has been revealed to synthesize substituted naphthalenes. This observation was further exploited develop an efficient approach for the construction naphthalenes from simple and commercially available 1,3-dicarbonyl compounds 1,2-bis(halomethyl)benzene via a new domino reaction sequence.

Abstract We herein describe the development of a dimerization procedure for amino acids to prepare 2,5‐disubstituted thiazoles and oxazoles in presence Na 2 S⋅9H O H O, respectively. These approaches enabled direct formation five‐membered ring systems bearing two different heteroatoms from acid units. Mechanically, decarboxylation, deamination, S/O insertion, cyclization gradient oxidation processes were involved oligomer formation. magnified image

The pyrazolo-azepino-centred polyheterocyclic fused system is a privileged scaffold, but it lacks an effective synthetic approach, with modular synthesis being even more scarce.

An oxidative trimerization of three amino acids has been realized to furnish 2,3,5-trisubstuitued pyridines in both cross- and homo-trimerization types. This method is capable converting simple linear biomass material heterocycles, which features the assembly acid branched chains into one aromatic ring. Molecular iodine triggers sequential decarboxylation deamination then promotes selective formation new C–N C–C bonds.

An expeditious one-step synthesis of the imidazopyridoindole scaffold was achieved through C-H oxidation/two-fold cyclization reaction methyl ketone and tryptamine derivatives. Mild oxidizing conditions were employed to realize efficient oxidation C(sp3)-H bonds, while suppressing overoxidation intermediate ensuring cross-trapping two in situ generated acylimine intermediates.

Abstract Lignans, in spite of their structural diversity, are all biosynthetically derived from coniferyl alcohol. We report herein a divergent synthesis lignans biomass-derived monolignols short synthetic sequence. Blue LED irradiation dichloromethane solution dicinnamyl ether derivatives the presence Cu(TFA) 2 , an alcohol (2.0 equiv) and catalytic amount Fukuzumi’s salt affords C7-alkoxylated aryltetralin cyclic ethers. Increasing under otherwise identical conditions diverts reaction...

An efficient base-promoted C(sp3)–H bond functionalization strategy for the synthesis of multisubstituted chromans from formal [3+3] cycloaddition benzo[c]oxepines and electron-rich phenols has been developed. The corresponding 4H-chromenes can be easily obtained in excellent yields by simple filtration chromans. Preliminary mechanistic studies indicate that C–O cleavage is key step this reaction could have occurred through tandem cleavage/Michael addition/annulation reactions.

We herein report an efficient synthesis of 2-aroyl-3-arylquinolines from phenylalanines and anilines. The mechanism involves I2-mediated Strecker degradation enabled catabolism reconstruction amino acids a cascade aniline-assisted annulation. Both DMSO water act as oxygen sources in this convenient protocol.

Precise control of the chemoselectivity halogenation a substrate equipped with multiple nucleophilic sites is highly demanding and challenging. Most reported chlorinations methyl ketones show poor compatibility or even exclusive selectivity toward electron-rich arene, olefin, alkyne residues. This attributed to direct in situ employment electrophilic Cl2/Cl+ species. Here, we that, bearing those competitive residues, can still undergo dichlorination afford α,α-dichloroketones chemo-specific...