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Buchwald–Hartwig versus Microwave-Assisted Amination of Chloroquinolines: En Route to the Pyoverdin Chromophore
Synlett ( IF 1.7 ) Pub Date : 2020-05-18 , DOI: 10.1055/s-0040-1707810 Sabine Laschat 1 , Philipp Seubert 1 , Marcel Freund 1 , Richard Rudolf 1 , Yulin Lin 1 , Luca Altevogt 1, 2 , Ursula Bilitewski 2 , Angelika Baro 1
Synlett ( IF 1.7 ) Pub Date : 2020-05-18 , DOI: 10.1055/s-0040-1707810 Sabine Laschat 1 , Philipp Seubert 1 , Marcel Freund 1 , Richard Rudolf 1 , Yulin Lin 1 , Luca Altevogt 1, 2 , Ursula Bilitewski 2 , Angelika Baro 1
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The reaction of 2-chloro-6,7-dimethoxy-3-nitroquinoline with a series of amines and aminoalkanoates under basic microwave-mediated conditions and under Buchwald–Hartwig amination conditions is reported. The microwave irradiation favored the reaction with amines, resulting in yields of up to 80%, whereas amino acid functionalization gave yields comparable to those of Buchwald–Hartwig amination. tert-Butyl (2R)-4-[(6,7-dimethoxy-3-nitroquinolin-2-yl)amino]-2-hydroxybutanoate was successfully cyclized to the pyoverdin chromophore, a subunit of siderophores.
中文翻译：
Buchwald-Hartwig 与微波辅助的氯喹啉胺化：通往 Pyoverdin 生色团的途中
报道了 2-氯-6,7-二甲氧基-3-硝基喹啉与一系列胺和氨基链烷酸酯在碱性微波介导条件和 Buchwald-Hartwig 胺化条件下的反应。微波辐射有利于与胺的反应，产率高达 80%，而氨基酸官能化的产率与 Buchwald-Hartwig 胺化的产率相当。叔丁基 (2R)-4-[(6,7-dimethoxy-3-nitroquinolin-2-yl)amino]-2-hydroxybutanoate 被成功环化为 pyoverdin 生色团，铁载体的一个亚基。
更新日期：2020-05-18
中文翻译：
Buchwald-Hartwig 与微波辅助的氯喹啉胺化：通往 Pyoverdin 生色团的途中
报道了 2-氯-6,7-二甲氧基-3-硝基喹啉与一系列胺和氨基链烷酸酯在碱性微波介导条件和 Buchwald-Hartwig 胺化条件下的反应。微波辐射有利于与胺的反应，产率高达 80%，而氨基酸官能化的产率与 Buchwald-Hartwig 胺化的产率相当。叔丁基 (2R)-4-[(6,7-dimethoxy-3-nitroquinolin-2-yl)amino]-2-hydroxybutanoate 被成功环化为 pyoverdin 生色团，铁载体的一个亚基。
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