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Highly selective acylation of polyamines and aminoglycosides by 5-acyl-5-phenyl-1,5-dihydro-4H-pyrazol-4-ones

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Abstract

5-Acyl-5-phenyl-1,5-dihydro-4H-pyrazol-4-ones, accessible from arylpropargyl phenyldiazoacetates, are highly selective acyl transfer reagents for di- and polyamines, as well as aminoalcohols and aminothiols. As reagents with a carbon-based leaving group, they have been applied for benzoyl transfer with a broad selection of substrates containing aliphatic amino in combination with other competing nucleophilic functional groups. The substrate scope and levels of selectivity for direct benzoyl transfer exceed those of known benzoylating reagents. With exceptional selectivity for acylation between primary amines bound to primary and secondary carbons, these new reagents have been used in direct site-selective monobenzoylation of aminoglycoside antibiotics.

Graphical abstract: Highly selective acylation of polyamines and aminoglycosides by 5-acyl-5-phenyl-1,5-dihydro-4H-pyrazol-4-ones

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Publication details

The article was received on 20 Jul 2017, accepted on 29 Aug 2017 and first published on 30 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC03184J
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Highly selective acylation of polyamines and aminoglycosides by 5-acyl-5-phenyl-1,5-dihydro-4H-pyrazol-4-ones

    K. O. Marichev, E. C. Garcia, K. C. Bhowmick, D. J. Wherritt, H. Arman and M. P. Doyle, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC03184J

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