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Three‐component Synthesis of Functionalized N ‐Protected Tetrasubstituted Pyrroles by an Addition‐Elimination‐Aromatization Process
Author(s) -
Magar Dhananjay R.,
Ke YiJiun,
Chen Kwunmin
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201200193
Subject(s) - aromatization , chemistry , ceric ammonium nitrate , yield (engineering) , pyrrole , amine gas treating , organic chemistry , component (thermodynamics) , combinatorial chemistry , catalysis , materials science , metallurgy , grafting , polymer , physics , thermodynamics
A three‐component, one‐pot, synthesis of N ‐protected tetrasubstituted pyrroles has been developed by treating nitroallylic acetates with an amine and a β‐keto ester mediated by ceric ammonium nitrate in MeOH. By this method, a diverse array of N ‐protected pyrrole 2,4‐dicarboxylic acid derivatives have been synthesized in 37–76 % yield. The reactions proceed smoothly through an interesting S N 2’ displacement and aromatization process.