57575-88-9

Upstream product

• 6876-66-0 4,4'-dimethylbenzanilide 
• 106-49-0 p-toluidine 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 36638-99-0 5-methyl-1-(4-methyl-N-p-tolyl-benzimidoyl)-1H-pyrazole-3-carboxylic acid methyl ester 
• 84901-02-0 5,7-Diphenyl-2-p-tolyl-[1,3,4]thiadiazolo[3,2-a]pyridin-4-ylium; chloride 
• 106-49-0 p-toluidine 
• 36664-35-4 5-(4-chloro-phenyl)-1-(4-methyl-N-p-tolyl-benzimidoyl)-1H-pyrazole-3-carboxylic acid methyl ester 
• 106951-03-5 1,5-bis(4-methylphenyl)-1H-tetrazole 
• 378773-52-5 2,3-di-(p-tolyl)-quinazoline-4(3H)-one 
• 1011719-58-6 C₂₂H₁₇ClN₂O 
• 1011719-57-5 C₂₃H₂₀N₂O 
• 1011719-59-7 C₂₃H₁₇N₃O 
• 16107-84-9 6-methyl-4-phenyl-2-(p-tolyl)quinazoline 
• 87995-63-9 N¹-(2-Brom-4-methylphenyl)-N¹,4-dimethyl-N²-(4-methylphenyl)benzamidin 

Relevant academic research and scientific papers

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.

Synthesis of Quinazolines from N,N′-Disubstituted Amidines via I2/KI-Mediated Oxidative C-C Bond Formation

An I2/KI-promoted oxidative C-C bond formation reaction from C(sp3)-H and C(sp2)-H bonds has been used to construct quinazoline skeletons from N,N′-disubstituted amidines. The required substrates are readily prepared from the corresponding acyl chlorides, anilines, and alkyl/benzylamines by sequential amidation, chlorination, and amination reactions. Under the optimal oxidative cyclization conditions, all these amidines were conveniently transformed into the expected products in moderate to good yields. This practical and environmentally benign approach works well with crude amidine intermediates and can also be carried out on a gram scale.

Fluorescent benzene-centered mono-, bis- and tris-triazapentadiene-boron complexes

A series of novel benzene centered mono-, bis- and tris-1,3,5-triazapentadiene ligands 6a-e was synthesized and investigated with respect to their reactivity towards triphenylborane. The resulting blue-fluorescent boron complexes 14a-e with a six-membered

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.

Amides as precursors of imidoyl radicals in cyclisation reactions

Amides have been successfully used as precursors of imidoyl radicals for radical cyclisation. The amides have been converted to imidoyl selanides via reaction with phosgene to yield imidoyl chlorides followed by reaction with potassium phenylselanide. Imidoyl selanides were reacted with tributyltin hydride (Bu3SnH) as the radical mediator with triethylborane or AIBN as initiators to yield imidoyl radicals for cyclisation reactions. Imidoyl radicals have been cyclised onto alkenes to yield 2,3-substituted-indoles and -quinolines and also onto pyrroles and indoles to give bi- and tricyclic heteroarenes.

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.

TETRAZOLES. XXVIII PREPARATION AND PROPERTIES OF 2,3-DIPHENYL-5-ALKYLTETRAZOLIUM SALTS

The oxidation of 1,5-diphenyl-3-alkylformazanes by potassium permanganate in methylene chloride (chloroform)-water two-phase systems is a convenient method for the preparation of 2,3-diphenyl-5-alkyltetrazolium salts.The 2,3-diphenyl-5-alkyltetrazolium salts can be used as catalysts for interphase transfer in reactions proceeding in organic solvent-water two-phase systems, with a neutral or acid aqueous phase.The catalytic activity of 2,3-diphenyl-5-alkyltetrazolium salts increases with increase in the length of the alkyl substituent in the 5-position of the tetrazole ring.

Carbanionically Induced -Migrations of ?- and Coordinatively Unsaturated Groups

According to a general reaction scheme, o-lithioaryl esters 4a,b, amides 13a,b 17b, and amidines 39b of non-enolizable carboxylic acids as well as a corresponding diphenylphosphinic amide 51b react under mild conditions to give the intensely coloured lithium derivatives of o-acylphenoles 6a,b and o-acylarenamines 15a,b, 18a, 41a, 52a, which are finally hydrolyzed to the neutral products 7a,b, 14a,b, 18b, 41b, 52b, respectively.The lithiated precursors of the rearrangement are mostly prepared by halogen/metal exchange reactions.In the case of N,N-di-p-tolylpivalamide 33 such a -rearrangement also could be induced by direct metalation of the educt.With N-methyl-N-phenylpivalamide (29), however, exclusive metalation of the N-methyl group occurs, followed by -migration of the pivaloyl group.Silyl groups, too, can undergo analogous -shifts, as was demonstrated by the rearrangement of the o-lithiated N-(trimethylsilyl)aniline 63b to the o-(trimethylsilyl)anilines 65a,b.When a benzoyl and sulfonyl group can compete for the -shifts, as in the N-tosylated benzamide 47b, only the benzoyl group migrates.However, the migration tendency of the trimethylsilyl group equals that of the benzoyl group as was shown with the N-silylated benzamide 66b.