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Unexpected Course of the Reaction of 2‐Unsubstituted 1 H ‐Imidazole 3‐Oxides with Ethyl Acrylate
Author(s) -
Mlostoń Grzegorz,
Urbaniak Katarzyna,
Wojciechowska Alicja,
Linden Anthony,
Heimgartner Heinz
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100519
Subject(s) - chemistry , imidazole , ethyl acrylate , acrylate , adduct , catalysis , cycloaddition , medicinal chemistry , oxide , methyl acrylate , organic chemistry , polymer chemistry , copolymer , polymer
The attempted ethenylation at C(2) of 2‐unsubstituted 1 H ‐imidazole N ‐oxides with ethyl acrylate (=prop‐2‐enoate) in the presence of Pd(OAc) 2 does not occur. In contrast to the other aromatic N ‐oxides, the [2+3] cycloaddition of imidazole N ‐oxides predominates, and 3‐hydroxyacrylates, isomeric with the cycloadducts, are key products for the subsequent reaction. The final products were identified as dehydrated 2+1 adducts of 1 H ‐imidazole N‐ oxide and ethyl acrylate. The role of the catalyst is limited to the dehydration of the intermediate 3‐hydroxypropanoates to give 1 H ‐imidazol‐2‐yl‐substituted acrylates.