37613-10-8

Upstream product

• 6833-15-4 4-chlorobenzanilide 
• 122-01-0 4-chloro-benzoyl chloride 
• 62-53-3 aniline 
• 2998-98-3 (Z)-(4-chlorophenyl)(phenyl)methanone oxime 

Downstream Products

• 109809-97-4 5-ethyl-2-(4-chloro-phenyl)-6-methyl-3-phenyl-3H-pyrimidin-4-one 
• 91790-87-3 N,N'-diphenyl-4-chlorobenzamidine 
• 71047-77-3 2-(4-chlorophenyl)-3-phenyl-(3H)-quinazolin-4-one 
• 2362-79-0 N-(4-chlorobenzylidene)aniline 
• 21010-43-5 N-(2-Chlor-ethyl)-N-phenyl-4-chlorbenzamid 
• 103755-10-8 2-(4-chloro-phenyl)-6-methyl-3-phenyl-5-propyl-3H-pyrimidin-4-one 
• 104-88-1 4-chlorobenzaldehyde 
• 62-53-3 aniline 
• 34747-76-7 4-Chloro-N-phenyl-benzimidoyl isothiocyanate 
• 6833-15-4 4-chlorobenzanilide 
• 168006-74-4 (4-chloro-phenylmethylidyne)-phenyl-ammonium 
• 1073487-00-9 2-phenyl-3-(4-chlorophenyl)-4-carboxylic acid ethyl ester-isoquinolin-1(2H)-one 

Relevant academic research and scientific papers

Regioselective Synthesis of Trisubstituted Quinoxalines Mediated by Hypervalent Iodine Reagents

A facile and regioselective synthesis of quinoxalines, an important motif in medicinal chemistry and materials sciences, was developed. Despite their prospective utility, the regioselective preparation of trisubstituted quinoxalines has not been previously established. In the reported system, hypervalent iodine reagents catalyzed the annulation between α-iminoethanones ando-phenylenediamines in a chemo/regioselective manner to afford trisubstituted quinoxalines. Excellent regioselectivities (6:1 to 1:0) were achieved using [bis(trifluoroacetoxy)iodo]benzene and [bis(trifluoroacetoxy)iodo]pentafluorobenzene as annulation catalysts.

Synthesis of Nitrogen-Containing Polyaromatics by Aza-Annulative π-Extension of Unfunctionalized Aromatics

Nitrogen-containing polycyclic aromatic compounds (N-PACs) are an important class of compounds in materials science. Reported here is a new aza-annulative π-extension (aza-APEX) reaction that allows rapid access to a range of N-PACs in 11–84 % yields from readily available unfunctionalized aromatics and imidoyl chlorides. In the presence of silver hexafluorophosphate, arenes and imidoyl chlorides couple in a regioselective fashion. The follow-up oxidative treatment with p-chloranil affords structurally diverse N-PACs, which are very difficult to synthesize. DFT calculations reveal that the aza-APEX reaction proceeds through the formal [4+2] cycloaddition of an arene and an in situ generated diarylnitrilium salt, with sequential aromatizations having relatively low activation energies. Transformation of N-PACs into nitrogen-doped nanographenes and their photophysical properties are also described.

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines

A single-pot procedure for the synthesis of 2,4-diarylquinazolines is described which involves a silver oxide-mediated C–H activation/C–N bond formation process. The generality of this method with respect to substituent effects is presented along with studies leading to process optimization. Mechanistic investigations provide support for the involvement of radical intermediates in the reaction process.

One-pot synthesis of polyfunctionalized quinolines: Via a copper-catalyzed tandem cyclization

An efficient one-pot approach for the synthesis of polyfunctionalized quinolines was developed via a sequence of copper-catalyzed coupling reaction/propargyl-allenyl isomerization/aza-electrocyclization. Easily available starting materials, mild conditions, and a wide substrate scope make this approach potentially useful.

Transition Metal-Free Visible Light-Driven Photoredox Oxidative Annulation of Arylamidines

A fast catalytic synthesis of multisubstituted quinazolines from readily available amidines via visible light-mediated oxidative C(sp3)-C(sp2) bond formation has been established. This reaction is a metal-free oxidative coupling catalyzed by a photoredox organocatalyst. The protocol features low catalyst loading (1 mol %).

Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines

A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp3)-C(sp2) and C(sp 2)-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp3C-H/sp2C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.

Palladium-catalyzed cyclocarbonylation of o-lodoanilines with Imidoyl Chlorides to produce quinazolin-4(3H)-ones

A wide variety of substituted quinazolin-4(3H)-ones were prepared in 63-91% yields by the palladium-catalyzed cyclocarbonylation of o-iodoanilines with imidoyl chlorides and carbon monoxide. The reaction is believed to proceed via in situ formation of an amidine, followed by oxidative addition, CO insertion, and intramolecular cyclization to give the substituted quinazolin-4(3H)-ones.

Synthesis and Biological Evaluation of 2,3,5-Substituted [1,2,4]Thiadiazoles as Allosteric Modulators of Adenosine Receptors

A number of 2,3,5-substituted [1,2,4]thiadiazole analogues of SCH-202676 (N-(2,3-diphenyl-[1,2,4]thiadiazole-5(2H)-ylidene)methanamine, 7a) were synthesized and tested as potential allosteric modulators of adenosine receptors. All compounds were capable of displacing the binding of the radiolabeled agonist [3H]CCPA to human A1 adenosine receptors, whereas modest and varying effects were observed on the binding of [3H]DPCPX, a radiolabeled antagonist for this receptor subtype. Four compounds, 7a (SCH-202676), 7k (LUF5792), 71 (LUF5794), and 8e (LUF5789), were selected for more detailed characterization. They all proved allosteric inhibitors of agonist binding, with 7k being most potent, whereas their effects on antagonist binding were more ambiguous. Subsequently, experiments were done on human adenosine A2A and A3 receptors. Compounds 7a and 7l displayed peculiar displacement characteristics of both radiolabeled agonist and antagonist binding to A2A receptors, whereas 7a showed some activity on A3 receptors.

N-arylbenzonitrilium ions. Photochemical generation and effect of substituents in the phenyl rings on lifetimes in water and reactivity with azide ion

Nitrilium ions Ar-C≡N+-Ar′ have been studied by laser flash photolysis in aqueous solutions containing 20% acetonitrile. The cations were generated by photoheterolysis of benzimidate esters Ar-CZ=N-Ar′ (Z = -OC6H4-4-CN) with 4-cyanophenoxide as the photochemical leaving group. Rate constants for the reaction with water (kw), azide ion (kaz) and hydroxide (kOH) were measured. The cation Ph-C≡N+-Ph is only 50-fold shorter lived in water compared to Ph-C≡N+-iPr (2); thus the effect of replacing an N-alkyl group with N-phenyl is modest. These two cations are also shown to have similar lifetimes to iminium analogs, e.g. Ph-CH=N+ (Me)-Ph. Thus, addition of water to analogous sp and sp2 hybridized systems occurs at a similar rate, and the increased steric access to the nitrilium plays at most a modest role. For the series where substituents in Ar′ were varied with Ar equal to phenyl, the Hammett plot for log kw correlated with σ, with ρ = - 1.4. For the series where Ar was varied, the data correlated much better with σ+, although ρ+ was only -0.6. This remarkably small effect of substituents in Ar constrasts with the effects seen in benzylic carbocations, but is consistent with the nitrilium structure, with most of the positive charge located on the nitrogen. Rate constant ratios kaz:kw, including the N-alkylnitrilium ion 2, are constant at ～104, with values of kaz well below the diffusion limit, even for the most reactive nitrilium ions. This is very different behaviour from that of carbocations and arylnitrenium ions of similar lifetimes in water. For these cations the rate constants kaz would be at or at least approaching the diffusion limit.