6578-15-0Relevant articles and documents
Regioselective and solvent-free arylation of β-nitrostyrenes with mono- and dialkyl anilines
Ranjbari, Mohammad A.,Tavakol, Hossein,Manoukian, Meghmik
, p. 709 - 721 (2020/10/23)
A green and solvent-free method were developed for alkylation of N,N-dialkylanilines with substituted β-nitrostyrenes using 10?mol% of choline chloride-zinc chloride deep eutectic solvent at 70?°C. The reaction was highly regioselective and only para-substituted products have been prepared. Despite the sensitivity and weak reactivity of the aniline derivatives for the Friedel–Crafts reaction in acidic media, the presented procedure was successfully carried out this transformation. The synthetic protocol was expanded for the alkylation of pyrrole and indole to produce pharmaceutically active compounds. The reduction of the nitro group of the product to amine was performed using Pd/C and hydrazine to produce amphetamine structure.
Friedel-Crafts alkylation reaction with fluorinated alcohols as hydrogen-bond donors and solvents
Tang, Ren-Jin,Milcent, Thierry,Crousse, Benoit
, p. 10314 - 10317 (2018/03/26)
An effective and clean FC alkylation of indoles and electron-rich arenes with β-nitroalkenes in HFIP was reported. The desired products are formed rapidly in excellent yields under mild conditions without the need for any additional catalysts or reagents. Further, this methodology can be applied to one-pot synthesis of biologically active tryptamine derivatives.
