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Direct Synthesis of 5‐Aryl Barbituric Acids by Rhodium(II)‐Catalyzed Reactions of Arenes with Diazo Compounds
Author(s) -
Best Daniel,
Burns David J.,
Lam Hon Wai
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502324
Subject(s) - diazo , rhodium , barbituric acid , chemistry , aryl , catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry , alkyl
A commercially available rhodium(II) complex catalyzes the direct arylation of 5‐diazobarbituric acids with arenes, allowing straightforward access to 5‐aryl barbituric acids. Free NH groups are tolerated on the barbituric acid, with no complications arising from NH insertion processes. This method was applied to the concise synthesis of a potent matrix metalloproteinase (MMP) inhibitor.