A simple approach to the synthesis of highly functionalized 3-alkylidene-2,3-dihydro-1H-pyrrole-2-ol derivatives and related pyrroles.
The reaction of various primary amines with acetylenic esters at ambient temperature in THF/H(2)O (50:50) produced related enaminones. Subsequently reaction of these in situ prepared enaminones with dibenzoylacetylene leads to 3-alkylidene-2,3-dihydro-1H-pyrrol-2-ol derivatives in good yields. The reaction of these products with various alcohols in the presence of a catalytic amount of HCl produced highly functionalized pyrroles in nearly quantitative yields.
Nasiri
Farough
F
Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran. FNasiri@uok.ac.ir
Pourdavaie
Kourosh
K
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D011758:Pyrroles / Q000138:chemical synthesis*
D011758:Pyrroles