Benzoyl azides were used for the direct and atom economic C–H amidation of electron rich heteroarenes in presence phosphoric acid, a photocatalyst visible light.

We report the synthesis of various phthalazines

PdCl2(MeCN)2 in combination with dppp proved to be a powerful and efficient catalyst for the coupling of sterically hindered N-arylsulfonylhydrazones aryl halides, thus providing flexible convergent access tetrasubstituted olefins related iso-combretastatin A4 good yields. This new protocol has been applied successfully formal synthesis biphenylisopropylidene 4-pyridine CYP17 inhibitor, 12b, biological interest.

Legionella pneumophila, a bacterium that replicates within aquatic amoebae and persists in the environment as free-living microbe, is causative agent of Legionnaires' disease. Among many species described, L. pneumophila associated with 90% human disease, 15 serogroups (Sg), Sg1 causes more than 84% disease worldwide. Thus, rapid specific identification utmost importance for evaluation contamination collective water systems risk posed. Previously we had shown about 20 kb 33-kb locus carrying...

Carbon–carbon bond formation reactions are of longstanding interest in organic chemistry. Improvements the methods targeting its creation still being performed, especially thanks to development innovative methodologies transition metal catalysis and photocatalysis. This review will tackle combination photoredox cycles create carbon–carbon bonds, focusing on four metals most reported literature this domain: Ni, Pd, Au Cu.

A silver-catalyzed cycloisomerization reaction of a series o-alkynylbenzohydroxamic acids is reported. Several 5-exo-dig and 6-endo-dig modes cyclization were observed with the nitrogen or oxygen atoms amide group acting as nucleophiles. The selectivity was strongly dependent on silver salt used presence triphenylphosphine an additive. Indeed, while use Ag2O at room temperature allowed isolation isobenzofuran-1-one oximes (7 compounds, 48–92% yield), [Ag(Im)]n concomitant addition 2 equiv...

Unprotected thioglycosides were effective nucleophiles for Ni(0)-catalyzed C-S bond-forming reaction with functionalized (hetero)aryl, alkenyl, and alkynyl halides. The functional-group tolerance on the electrophilic partner was typically high anomeric selectivities of in all cases. efficiency this general procedure well-demonstrated by synthesis 4-methyl-7-thioumbelliferyl-β-D-cellobioside (MUS-CB).

Abstract An efficient and unprecedented palladium‐catalyzed S‐glycosylation reaction of a range alkenyl alkynyl halides by using thiosugars as nucleophile partners has been established. With palladium diacetate in combination with Xantphos the catalytic system, variety β‐alkenylthioglycosides well β‐alkynylthioglycosides can be prepared good to excellent yields. The efficiency this general protocol was well‐demonstrated formal synthesis leaf‐closure β‐glucosidase inhibitor. magnified image

The synthesis and structure–activity relationships associated with a series of 1,1-diarylethylene tubulin polymerization inhibitors 3 4 are described. key step for their preparation involves palladium-catalyzed coupling N-arylsulfonylhydrazones aryl halides, thus providing flexible convergent access to tri- tetrasubstituted 1,1-diarylolefins related isocombretastatin A-4 (isoCA-4). These compounds have been evaluated inhibitory activity as well cytotoxic activity. most potent...

Accessibility of highly functionalized polyheterocyclic compounds with efficient catalytic methods represents a long-standing challenge for organic chemists. The use transition metal catalysts and the recent development gold(III) complexes opens new opportunities. We herein report straightforward gold(III)-catalyzed domino cyclization / functionalization reactions to access scaffolds biological interest. methodology developed here is applied synthesis isochromenes through...

Abstract α‐ and β‐thioglycosides serve as effective nucleophiles for Buchwald–Hartwig cross‐coupling reactions using functionalized (hetero)aryl halides. The functional group tolerance on the electrophilic partner is typically high, both benzyl acetate protecting groups carbohydrate are tolerated, anomer selectivities of thioglycosides high in all cases studied. efficiency this general protocol was well demonstrated by synthesis 4‐methyl‐7‐thioumbelliferyl‐β‐ D ‐cellobioside (MUS‐CB).

Carbon–heteroatom bond formation is a long‐standing hot topic in organic chemistry owing to the ubiquitous presence of these bonds molecules. A major pathway form them heterofunctionalization unsaturated moieties mediated by transition metals or radical initiators. Recently, visible‐light catalysis has become powerful method for synthesis many chemical bonds, and carbon–heteroatom attracted particular attention photochemists. In this review, we highlight recent advances photocatalysis C–N,...

Visible light catalysis allows the regioselective synthesis of oxazolines in high yields. The mild photosensitized manifold leverages intermolecular formation with a wide functional group tolerance on both benzoyl azides and alkenes partners. Mechanistic investigations suggest sensitization azide moiety as key activation step.

Research on synthesizing nitrogen-containing heterocyclic scaffolds is important because these structures are commonly found in Nature, such as the alkaloids' family. In our study, we propose a new method to synthesize isoquinoline core using an electron donor-acceptor (EDA) complex strategy. Our mechanistic investigations have confirmed that synthesis process operates through EDA mechanism, which not extensively discussed literature, particularly regarding its applications alkynyl...

A mild and general method for the direct alkynylation of azoles such as pyrrole, indole, 7-azaindole is described here. Using a simple catalytic system Pd(OAc)2 (2.5 mol %), P(tBu)2Me·HBF4 (5 NaOAc (2 equiv) allowed regioselective introduction various alkynyl residues at C-2 position pyrroles. Interestingly, was also observed on C-3-substituted indoles, whereas classical C-3 obtained selected unsubstituted indoles 7-azaindole. Our methodology has been illustrated by efficient synthesis...

In this review we chose to concentrate on the bibliography data from 2013 2015 (until February), related application of Inverse Electron Demand Diels-Alder (IEDDA) reaction synthesis heterocycles, as building blocks for natural products synthesis. Moreover, IEDDA recently developed bioorthogonal ligations (in 2008), using tetrazines moieties diene partners, and engineered alkenes or alkynes dienophiles, will be detailed. The in vivo applications are particularly amazing undoubtedly...

Abstract An efficient method for the selective mono‐N‐arylation of 1‐aminoazoles to provide a range N ‐aryl‐1‐aminoazoles in good yields is described. This process based on use tris(dibenzylideneacetone)dipalladium associated Xphos as catalyst system general, and allows coupling proceed, first time, with variety cheaper less reactive aryl chlorides. The sequential combination monoarylation using chlorides second N‐arylation reaction (hetero)aryl bromides iodides proved be useful rapid...

An efficient and general palladium-catalyzed coupling of 3-chloro-quinoxalinones with a variety nitrogen-containing nucleophiles such as (hetero)aromatic aliphatic amides well some challenging weakly nucleophilic nitrogen compounds including lactams, carbamates NH-containing azoles is described. In all cases, the reactions take place rapidly cleanly in dioxane using Pd(OAc)2 catalyst, Xantphos ligand K2CO3 base furnishing 3-N-substituted quinoxalinone products good to excellent yields.

An efficient silver-catalyzed tandem reaction for the formation of 1,2-dihydroisoquinoline derivatives is herein reported. Highly functionalized multiheterocyclic scaffolds are accessible in a straightforward manner using readily starting materials under mild conditions. This methodology offers an attractive route synthesis and development biologically relevant new heterocyclic pharmacophore, merging biological activities isoquinolines with those various nitrogen-containing heterocycles...

Rearrangement reactions in organic chemistry are attractive strategies to build efficiently complex scaffolds, just one step, from simple starting materials. Among them, aryl migrations certainly of the most useful and straightforward rearrangement for building carbon–carbon bonds. Of note, anionic migration have been largely described compared their radical counterparts. Recently, visible-light catalysis has proven its efficiency generate such rearrangements due concomitant loss a particle...

Abstract Background Despite the improvement of relapse-free survival mediated by anti-angiogenic drugs like sunitinib (Sutent®), or combinations with immunotherapy, metastatic clear cell Renal Cell Carcinoma (mccRCC) remain incurable. Hence, new relevant treatments are urgently needed. The VEGFs coreceptors, Neuropilins 1, 2 (NRP1, 2) expressed on several tumor cells including ccRCC. We analyzed role VEGFs/NRPs signaling in ccRCC aggressiveness and evaluated relevance to target this pathway....

Visible-light catalysis is now widely acknowledged as a potent approach for efficiently constructing various types of frameworks, particularly bioactive compounds, with high yields. However, there still strong need further advancements in these methods because certain delicate compounds cannot be synthesized due to structural sensitivity. In this context, seamless reaction pathway toward 6-membered ring nitrogen-containing heterocycles presented here, offering access isoquinoline derivatives...

Diazo compounds as well their precursors represent an interesting category for organic synthesis. Particularly N-tosylhydrazones, have attracted attention easy accessibility and diverse reactivity, including carbene transfer reactions. We described a visible light induced N-H insertion reaction of anilines on in-situ generated diazo compounds. Optimal conditions using DBU in toluene yielded desired products efficiently. Mechanistic studies enabled us to trap intermediate that has key role...

The synthesis of new heterocyclic structures is a challenging endeavor in organic chemistry. It requires the development innovative methods that can generate novel frameworks, thereby allowing exploration uncharted chemical spaces for potential applications. In this context, Halogen-Bonding-Assisted EDA-SET strategy presents promising and efficient approach. our study, we propose employing to facilitate diverse phosphorus-based scaffolds, which hold significant future research endeavors. By...