22050-14-2

Upstream product

• 5883-82-9 2-((4-methoxyphenyl)amino)-1-phenylethanone 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 104-94-9 4-methoxy-aniline 
• 70-11-1 α-bromoacetophenone 
• 100-42-5 styrene 
• 75-52-5 nitromethane 
• 100-52-7 benzaldehyde 
• 102-96-5 (2-nitroethenyl)benzene 
• 1189054-24-7 dimethyl 4-phenyl-1-(4-methoxyphenyl)-2,4-dihydro-1H-pyrrole-2,3-dicarboxylate 

Relevant academic research and scientific papers

Phosphine-Catalyzed Synthesis of Chiral N-Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling

Phosphine-catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1H-pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.

Synthetic method of pyrrole derivatives

The invention provides a synthetic method of pyrrole derivatives, comprising the steps of: successively adding amine, electron-withdrawing alkyne and olefin in a reaction container according to the molar ratio of 1:1-1.4:1.3-4, adding in the solvent according to the ratio of 1mmol of amine added in 2-4mL of solvent, and then adding 0.8-2% molar ratio of catalyst Pd(OAc)2, 1.8-4% amine molar ratio of oxidizing agent K2S2O8, 2mL of acetic acid and 2mL of hexanenitrile; reacting for 15-24h at 100oC-120oC of oilbath; cooling to room temperature, adding water, extracting for three times by ethyl acetate, combining an organic layer, decompressing and concentrating, carrying out column chromatography and purification to the product, and obtaining the product of pyrrole derivatives. The method provided in the invention has simple reaction and operation, cheap reaction substrate, high yield, good selection, easy separation and purification and little pollution.

Regioselective Synthesis of 2,3,4-Trisubstituted Pyrroles via Pd(II)-Catalyzed Three-Component Cascade Reactions of Amines, Alkyne Esters, and Alkenes

A new, efficient, and versatile Pd(II)-catalyzed oxidative three-component cascade reaction of diverse amines, alkyne esters, and alkenes is disclosed for the direct synthesis of diverse 2,3,4-trisubstituted pyrroles with broad functional group tolerance and in good to excellent yields. This transformation is supposed to proceed through the cascade formation of C(sp2)-C(sp2) and C(sp2)-N bonds via Pd(II)-catalyzed regioselective alkene migratory insertion, intramolecular radical addition, and oxidation sequential processes.

A simple and efficient metal-free synthesis of tetrasubstituted pyrroles by iodine-catalyzed four-component coupling reaction of aldehydes, amines, dialkyl acetylenedicarboxylates, and nitromethane

The four-component coupling reaction of aldehydes, amines, dialkyl acetylenedicarboxylates, and nitromethane in the presence of molecular iodine as a catalyst furnished the corresponding 1,2,3,4-tetrasubstituted pyrroles under reflux. The products are formed in high yields (65-88%) within 8 hours. The method is simple, efficient, cost-effective, and metal-free. Georg Thieme Verlag Stuttgart.

An efficient one-pot synthesis of tetra-substituted pyrroles

The three-component reaction of primary amines, dialkyl acetylenedicarboxylates and β-nitrostyrene derivatives in the presence of Iron(III) chloride afforded 1,2,3,4-tetra-substituted pyrroles in high yields. These reactions could precede via domino Micha

Efficient synthesis of functionalized 2,5-dihydropyrrole derivatives by Ph3P-promoted condensation between acetylene esters and α-arylamino ketones

A new and efficient one-pot synthesis of polysubstituted 2,5-dihydropyrrole derivatives by reaction between dialkyl acetylenedicarboxylates and β-aminoketones promoted by triphenylphosphine, is described. The prepared 2,5-dihydropyrroles can be easily oxi