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DOI: 10.1055/a-1644-2930
Oxalylacetylenes as Dielectrophiles for Annulation of Quinoline Rings: Synthesis of Highly Functionalized 1,3-Oxazinoquinolines
This work has been approved by plans for research projects at the IPC Russian Academy of Sciences (State Registration No. AAAA-A16-116112510005-7).
Abstract
Oxalylacetylenes act as dielectrophiles in the annulation of quinolines to give highly functionalized 1,3-oxazine cycles decorated with ethynyl, oxalyl, ester and aryl substituents. The annulation proceeds under mild conditions (room temperature, without catalyst) in 2:1 mode with respect to acetylene and quinoline to deliver 1,3-oxazinoquinolines in 45–88% yields. A beneficial feature of the reaction is that, in contrast to results on the reaction of quinolines with trifluoroacetylacetylenes in the presence of water, where H2O acted as a third electrophile, leading to the 1,3-oxazinoquinolines containing a hydroxyl group, this reaction well tolerates the aqueous medium. This reaction also tolerates isoquinoline and phenanthridine.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1644-2930.
- Supporting Information
Publikationsverlauf
Eingereicht: 02. August 2021
Angenommen nach Revision: 14. September 2021
Accepted Manuscript online:
14. September 2021
Artikel online veröffentlicht:
21. Oktober 2021
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