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- Title
A Convenient Synthesis of Novel Isoxazolidine and Isoxazole Isoquinolinones Fused Hybrids.
- Authors
Ouzounthanasis, Konstantinos A.; Rizos, Stergios R.; Koumbis, Alexandros E.
- Abstract
Isoxazolidine, isoxazole, and isoquinolinone rings are present in the structure of several natural products and/or pharmaceutically interesting compounds. In this work, facile and efficient pathways have been developed for the preparation of fused frameworks bearing those heterocycles. The successful approaches for both isoxazolidine/isoquinolinone and isoxazole/isoquinolinone hybrid syntheses relied initially on 1,3-dipolar cycloadditions of nitrones and nitrile oxides to indenone and 2-propargylbenzamide, respectively. The construction of the isoquinolinone lactam system followed by performing a selective Schmidt reaction for isoxazolidine derivatives (two steps overall), whereas the isoxazole lactams were reached via an Ullmann-type cyclisation (three steps overall). Key observations were made regarding the stereo- and regioselectivities of the reactions employed, and small libraries of the targeted hybrids were prepared, demonstrating the general applicability of these strategies.
- Subjects
NITRILE oxides; ISOXAZOLIDINES; SCHMIDT reaction; NATURAL products; RING formation (Chemistry); NITRONES; LACTAMS
- Publication
Molecules, 2024, Vol 29, Issue 1, p91
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules29010091