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Angew Chem Int Ed Engl. 2015 Jun 15;54(25):7410-3. doi: 10.1002/anie.201502324. Epub 2015 May 8.

Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds.

Author information

1
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK).
2
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK). hon.lam@nottingham.ac.uk.

Abstract

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 N-H groups are tolerated on the barbituric acid, with no complications arising from N-H insertion processes. This method was applied to the concise synthesis of a potent matrix metalloproteinase (MMP) inhibitor.

KEYWORDS:

arylation; barbituric acid; carbenes; diazo compounds; rhodium

PMID:
25959544
PMCID:
PMC4479025
DOI:
10.1002/anie.201502324
[Indexed for MEDLINE]
Free PMC Article

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