13633-36-8

Upstream product

• 106-49-0 p-toluidine 
• 513-31-5 2-bromoallyl bromide 

Downstream Products

• 364061-39-2 1,5-Dihydro-1-(4-methylphenyl)-3,4-bis(2-phenyl-2-phenylaminoethyl)-2H-pyrrole 
• 364061-40-5 1,5-Dihydro-3,4-bis(2-hydroxy-2-methylpropyl)-1-(4-methylphenyl)-2H-pyrrole 
• 50872-61-2 3,4-bismethylene-N-(4-methylphenyl)pyrrolidine 
• 545435-25-4 5-(4-bromobutyl)-2-(4-methylphenyl)-2,4,5,6-tetrahydrocyclopenta[c]pyrrol-5-ol 

Relevant academic research and scientific papers

Synthesis of pyrrole derivatives through functionalization of 3,4-bis(lithiomethyl)dihydropyrroles

Bis(2-lithioallyl)amines 2, substituted at the double bonds, undergo intramolecular carbolithiation of a lithiated double bond in different solvents to afford dilithiated dihydropyrroles 3. Treatment of these dianions with electrophiles allows the preparation of functionalized pyrrole derivatives 5 and 6. Interestingly, treatment of these dianions with carboxylic esters selectively affords either keto or hydroxy compounds (9 or 10), depending on the conditions. Several experiments have been carried out in order to clarify the mechanism of this selective transformation. Finally, dilithiated dihydropyrrole 3a could be transformed in a three-step procedure into the corresponding 3,4-bis(bromomethyl) derivative 31, which can easily be converted into bicyclic pyrrole compounds 32-33 by treatment with different nucleophiles. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Synthesis of functionalized pyrrole and indole derivatives through carbometallation of lithiated double bonds

Bis(2-lithioallyl)amines derived from bis(2-bromoallyl)amines undergo intramolecular carbometallation of a lithiated double bond, giving dilithiated dihydropyrroles. The cyclizations are promoted by N,N,N′,N′-tetramethylethylenediamine (TMEDA). Reaction of these intermediates with electrophiles allows the preparation of some new fused and nonfused five-membered functionalized heterocycles. Although 2-lithioallylamines do not suffer intermolecular carbometallation, dimerization products are obtained with their copper or zirconium derivatives. Finally, the application of this new reaction to 2-lithio-N-(2-lithioallyl)anilines leads to 3-lithiomethylindole derivatives, which are transformed to functionalized indole derivatives by reaction with electrophiles.