Journal
RSC ADVANCES
Volume 11, Issue 1, Pages 543-554Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ra08325a
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Funding
- Hungarian Research Foundation (OTKA) [K-129037]
- Ministry of National Economy, National Research Development and Innovation Office [GINOP-2.3.2-15-2016-00034]
- EU [EFOP-3.6.1-16-2016-00008]
- Ministry of Human Capacities, Hungary [TKP-2020]
- Ministry for Innovation and Technology [UNKP-20-3-SZTE-319]
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The synthesis of hydroxy-substituted kynurenic acid (KYNA) derivatives was achieved by an optimised Conrad-Limpach procedure, followed by a modified Mannich reaction. The newly introduced substituents altered the preferred reaction centre of the KYNA skeleton. Systematic investigation revealed that different reaction conditions led to mono- or disubstituted derivatives.
The syntheses of hydroxy-substituted kynurenic acid (KYNA) derivatives have been achieved by an optimised Conrad-Limpach procedure. The derivatives were then reacted with morpholine and paraformaldehyde, as a representative amine and aldehyde, in a modified Mannich reaction. The newly introduced substituents altered the preferred reaction centre of the KYNA skeleton. A systematic investigation of substitutions was carried out, using different reaction conditions, resulting in mono- or disubstituted derivatives. Product selectivity and regioselectivity were rationalised by DFT calculations disclosing HOMO distribution and NBO charges on the potential nucleophilic centres in the anion of the appropriate KYNA ester assumed to be active components towards the iminium ion intermediate.
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