N-Heterocycle-Triggered MCRs: An Approach to the Concise Synthesis of Perfluoroalkylated Spiro-1,3-oxazines

Abstract Multicomponent reactions involving methyl perfluoroalk-2-ynoates initiated by N-heterocycles (quinoline, isoquinoline, and benzothiazole) in the presence of isatins and diaryl 1,2-diketones allowed efficient access to trifluoromethyl- or other perfluoroalkyl-substituted spiro-1,3-oxazine de...

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Veröffentlicht in:Synthesis (Stuttgart) 2018-12, Vol.50 (23), p.4668-4682
Hauptverfasser: Liu, Gang, Wu, Yueci, Han, Jing, He, Weimin, Chen, Jie, Deng, Hongmei, Shao, Min, Zhang, Hui, Cao, Weiguo
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract Multicomponent reactions involving methyl perfluoroalk-2-ynoates initiated by N-heterocycles (quinoline, isoquinoline, and benzothiazole) in the presence of isatins and diaryl 1,2-diketones allowed efficient access to trifluoromethyl- or other perfluoroalkyl-substituted spiro-1,3-oxazine derivatives. This facile transformation is regioselective and proceeded smoothly through a 1,4-dipolar intermediate under mild conditions, affording the products in good to excellent yields.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1609563