34916-13-7

Upstream product

• 6833-18-7 4-methyl-N-phenylbenzamide 
• 62-53-3 aniline 
• 874-60-2 4-methyl-benzoyl chloride 
• 99-94-5 p-Toluic acid 

Downstream Products

• 6833-18-7 4-methyl-N-phenylbenzamide 
• 425366-12-7 phenyl-p-tolylmethylidyne-ammonium 
• 1402752-11-7 2-(4-methylphenyl)naphtho[2,3-d]oxaphosphole 
• 666723-15-5 N-(1-(4-methylphenyl)-2-propyn-1-ylidene)-benzenamine 
• 1428326-99-1 4-methyl-N-(2-(4-methylphenyl)-4-quinolinyl)-benzenesulfonamide 
• 1140916-82-0 N-[1-(4-methylphenyl)-3-trimethylsilyl-2-propinylidene]-aniline 
• 1628638-39-0 ethyl 2-(4-methylphenyl)quinazoline-4-carboxylate 
• 294644-40-9 4-methyl-N²-[(morpholin-4-yl)(selenocarbonyl)]-N¹-phenylbenzimidamide 
• 294644-59-0 ethyl 4-(4-methylphenyl)-2-(morpholin-4-yl)-1,3-selenazole-5-carboxylate 

Relevant academic research and scientific papers

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 %).

TETRAHYDROISOQUINOLIN-2-YL-(QUINAZOLIN-4-YL) METHANONE COMPOUNDS AS CANCER CELL GROWTH INHIBITORS

Tetrahydroisoquinolin-2-yl-(quinazolin-4-yl)methanone derivatives represented by formula (I), pharmacologically acceptable salts thereof, and compositions containing such compounds are described. Methods for treating hyperproliferative disorders by administering the compounds are also described. 1,2,3,4-tetrahydroisoquinoline derivatives for making tetrahydroisoquinolin-2-yl-(quinazolin-4-yl)methanone compounds are also described.

Palladium, iridium and ruthenium complexes with acyclic imino-N-heterocyclic carbenes and their application in aqua-phase Suzuki-Miyaura cross-coupling reaction and transfer hydrogenation

Palladium (4a-4c), iridium (5a-5c) and ruthenium (6a-6c) complexes have been prepared by in situ transmetalation from the corresponding silver complexes of acyclic imino-functionalized imidazolium chlorides [1-(Me)-imidazolium-3- {C(p-CH3-Ph)N(Ar)}]Cl (3) (Ar = 2,4,6-trimethylphenyl (3a), 2,6-diisopropylphenyl (3b) and phenyl (3c)) with [Pd(COD)Cl2], [Cp*IrCl2]2 or [Ru(p-cymene)Cl2] 2, respectively. Iridium and ruthenium complexes, 5a[PF 6]-5c[PF6], 6a[PF6]-6c[PF6], 6c[BF4], 6c[BPh4] and 6c[NTf2], were obtained directly from 5a-5c and 6a-6c through an anion-exchange process with KPF 6, NaBF4, NaBPh4 and LiNTf2 (bis(trifluoromethylsulfonyl)imide lithium), respectively. All complexes were characterized by FT-IR, 1H and 13C NMR spectroscopy and elemental analysis. Crystal structures of 4a, 5a and 6c[NTf2] show that five-membered chelate ring is formed in these complexes by the coordination of the carbene carbon and the imino nitrogen atom, and the latter two are cationic compounds with Cl- and NTf2- as counteranion respectively. The catalytic performance of Pd complexes for Suzuki-Miyaura cross-coupling reactions in pure water and Ir and Ru complexes for transfer hydrogenation of ketones and imines was tested in a wide scope of substrates. Pd complex 4b with the largest steric hinder exhibited the best performance to gain moderate to excellent yields on catalyzing Suzuki-Miyaura cross-coupling of aryl chlorides and arylboronic acids in water. While in transfer hydrogenation of various ketones, all the Ir and Ru complexes were effective with good to excellent yields. Among all these complexes, 6c[PF 6] was found most effective, and moderate yields could be obtained even in the transfer hydrogenation of imines. Moreover, different counteranions of Ru complexes are influential on catalyzing the transfer hydrogenation, with the sequence of PF6- ≈ BF4- > BPh4- > Cl- > NTf2 -.

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.

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.

Selenium-containing heterocycles from isoselenocyanates: Synthesis of 1,3-selenazoles from N-phenylimidoyl isoselenocyanates

The reaction of N-phenylbenzamides 5 with excess SOCl2 under reflux gave N-phenylbenzimidoyl chlorides 6, which, on treatment with KSeCN in acetone, yielded imidoyl isoselenocyanates of type 2. These products, obtained in almost quantitative yield, were stable in the crystalline state. They were transformed into selenourea derivatives 7 by the reaction with NH3, or primary or secondary amines. In acetone at room temperature, 7 reacted with activated bromomethylene compounds such as 2-bromoacetates, acetamides, and acetonitriles, as well as phenacyl bromides and 4-cyanobenzyl bromide to to give 1,3-selenazol-2-amines of type 9 (Scheme 2). A reaction mechanism via alkylation of the Se-atom of 7, followed by ring closure and elimination of aniline, is most likely (cf. Scheme 7). In the case of selenourea derivatives 7d and 7I with an unsubstituted NH2 group, an alternative ring closure via elimination of H2O led to 1,3-selenazoles 10a and 10b, respectively (Schemes 4 and 7). On treatment with NaOH, ethyl 1,3- selenazole-5-carboxylates 9I and 9s were saponified and decarboxylated to give the corresponding 5-unsubstituted 1,3-selenazoles 12a and 12b (Scheme 6). The molecular structures of selenourea 7f and the 1,3-selenazoles 9c and 9d have been established by X-ray crystallography (Figs. 1 and 3).

Syntheses and basicity of 4-(N,N-dimethylamino)-2-arylquinazolines

The reaction of substituted N-phenylbenzimidoyl chlorides with N,N-dimethylcyanamide in the presence of titanium tetrachloride has yielded seven 4-(N,N-dimethylamino)-2-arylquinazolines substituted on the phenyl ring with electron donating or withdrawing groups. pKa values have been determined for these compounds and analyzed in conjunction with the Hammertt σ constants to observe the influence of these phenyl substituents upon the basicity of 4-(N,N-dimemylamino)-2-arylquinazolines. The σ value, single crystal X-ray analysis and 15N-nmr spectra give evidence about the preferential site of protonation in such systems.