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Buchwald-Hartwig versus Microwave-Assisted Amination of Chloroquinolines: En Route to the Pyoverdin Chromophore
Seubert, Philipp Freund, Marcel Rudolf, Richard Lin, Yulin Altevogt, Luca Bilitewski, Ursula Baro, Angelika Laschat, Sabine
Seubert, Philipp
Freund, Marcel
Rudolf, Richard
Lin, Yulin
Altevogt, Luca
Bilitewski, Ursula
Baro, Angelika
Laschat, Sabine
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Issue Date
2020-07-22
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original manuscript
Adobe PDF, 606.69 KB
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supplementary materials
Adobe PDF, 5.18 MB
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Abstract
The reaction of 2-chloro-3-nitroquinoline and a series of amines and aminoalkanoates under basic microwave-mediated conditions and Buchwald-Hartwig amination conditions is reported. The microwave irradiation favored the reaction with amines, resulting in yields up to 80%, while amino acid functionalization gave yields comparable to those of BuchwaldHartwig amination. (2R)-4-[(6,7-dimethoxy-3-nitroquinolinyl)amino]-2-hydroxybutanoate could be successfully cyclized to the pyoverdin chromophore, a subunit of siderophores.
Citation
Synlett 2020 31 12 doi: 10.1055/s-0040-1707810.
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Article
Language
en
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ISSN
09365214
EISSN
14372096
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Sponsors
Ministerium für Wissenschaft, Forschung und Kunst Baden-Württemberg
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Attribution-NonCommercial-ShareAlike 4.0 International