21399-23-5

Upstream product

• 631-61-8 ammonium acetate 
• 64-19-7 acetic acid 
• 13145-56-7 1,4-bis(4-tolyl)butane-1,4-dione 
• 89108-49-6 1-(1-azidovinyl)-4-methyl benzene 
• 110-61-2 butanedinitrile 
• 5720-05-8 4-methylphenylboronic acid 
• 619-41-0 4-(bromoacetyl)toluene 
• 108-88-3 toluene 
• 26218-73-5 3,4-bis(4-methylphenyl)-1,2,5-oxadiazole-N-oxide 
• 66864-60-6 1,4-bis(4-methylphenyl)-2-butyne-1,4-dione 
• 5465-41-8 ditoluylethylene 
• 21399-33-7 bis-(1-p-tolyl-ethylidene)-hydrazine 

Relevant academic research and scientific papers

One-pot synthesis of pyrrole derivatives from (E)-1,4-diaryl-2-butene-1,4-diones

2,5-Di- and 1,2,5-trisubstituted pyrrole derivatives can be prepared conveniently from (E)-1,4-diaryl-2-butene-1,4-diones in a one-pot operation through domino-pathways via palladium-assisted transfer hydrogenation followed by a Paal-Knorr reaction using ammonium formate and its analogs.

Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles

The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.

Synthesis of 2,2,5-Trisubstituted 2 H-Pyrroles and 2,3,5-Trisubstituted 1 H-Pyrroles by Ligand-Controlled Site-Selective Dearomative C2-Arylation and Direct C3-Arylation

Palladium-catalyzed site-selective dearomative C2-arylation of 2,5-diaryl-1H-pyrroles with aryl chlorides was accomplished, and a series of 2,2,5-triaryl-2H-pyrroles were synthesized. In addition, the site selectivity of the reaction was switched by simply changing the ligand, and the direct C3-arylated 2,3,5-triaryl-1H-pyrroles were prepared. The obtained 2,2,5-triaryl-2H-pyrroles could be further transformed into 2,2,5,5-tetraarylpyrrolidines.

Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones

Several pyrrole derivates with multiple aryl substituents were prepared conveniently in a one pot-reaction from but-2-ene-1,4-diones and but-2-yne-1,4-diones via hydrogenation of the carbon-carbon double bond/triple bond followed by amination-cyclization. The reaction could be performed with ammonium formate or alkyl/arylammonium formates under Pd/C in polyethylene glycol-200 (PEG-200) under microwave irradiation. Using this procedure, different aryl-substituted pyrroles were prepared. Furthermore, studies on microwave vs thermal conditions indicate faster heating under microwave conditions was responsible for rate enhancement.

THERMAL HETEROCYCLIZATION OF METHYL ARYL KETAZINES. I. REACTIONS OF THE TAUTOMERIC DIENEHYDRAZINE FORM

The thermal reactions of methyl aryl ketazines in the range of 150-350 deg C were studied.Thermolysis is represented by three types of parallel-consecutive reactions of various tautomeric forms of the initial compounds, i.e., the dienehydrazine, the enehydrazine, and azine forms.The chemical transformations of the first type lead to the cyclization of the azines into derivatives of 2,5-diarylpyrrole and 3,6-diarylpyridazine.The formation of pyrroles under the conditions of uncatalyzed thermolysis and at temperatures excluding the possibility of processes involvingthe participation of radicals is consistent with the mechanism of a -sigmatropic shift.

NOVEL TYPES OF TRANSFORMATIONS OF α-AZIDOSTYRENE DERIVATIVES AND 3-ARYL-2H-AZIRINES IN THE PRESENCE OF HEXACARBONYLMOLYBDENUM

The reaction of α-azidostyrene derivatives with hexacarbonylmolybdenum was found to give 2,5-diarylpyrroles and acetophenone derivatives via a complexed 1-arylvinylnitrene intermediate, while that of 3-aryl-2H-azirines gave 2,4-diarylpyrroles in addition to acetophenone derivatives and 2,5-diarylpyrazines.