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Synthesis of N ‐Aryl‐5‐alkylidene‐2,5‐dihydropyrrol‐2‐ones by “Cyclization/Dimroth Rearrangement” Reactions of 1,3‐Dicarbonyl Dianions with Diimidoyl Dichlorides of Oxalic Acid
Author(s) -
Anders Joachim T.,
Görls Helmar,
Langer Peter
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300727
Subject(s) - chemistry , aryl , medicinal chemistry , oxalic acid , hydrolysis , domino , cleavage (geology) , organic chemistry , catalysis , alkyl , geotechnical engineering , fracture (geology) , engineering
The reaction of dilithiated dicarbonyl compounds with oxaldiimidoyl dichlorides resulted in regio‐ and ( E )/( Z )‐diastereoselective formation of 5‐alkylidene‐3‐arylamino‐2,5‐dihydropyrrol‐2‐ones. The products were formed by a domino “cyclization/Dimroth rearrangement” reaction. The mechanism and preparative scope of the cyclization was studied. The arylamino groups of the products were removed chemoselectively under mild conditions and in high yields by hydrolytic cleavage. The products, N ‐aryl‐5‐alkylidene‐3‐hydroxy‐2,5‐dihydropyrrol‐2‐ones, are of considerable interest from pharmacological and synthetic viewpoints. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)