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Regioselective synthesis of 3,4-diarylpyrimido[1,2- b ]indazole derivatives enabled by iron-catalyzed ring-opening of styrene oxides.
- Source :
-
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 Oct 10; Vol. 60 (82), pp. 11742-11745. Date of Electronic Publication: 2024 Oct 10. - Publication Year :
- 2024
-
Abstract
- The first synthesis of 3,4-diarylpyrimido[1,2- b ]indazole derivatives from 3-aminoindazoles has been realized. The FeCl <subscript>3</subscript> -catalyzed intermolecular epoxide ring-opening reaction altered the order of annulation, with the free primary NH <subscript>2</subscript> groups in 3-aminoindazoles preferentially reacting with styrene oxides instead of aromatic aldehydes. This protocol is further highlighted by its broad substrate compatibility, high chemo- and regioselectivities, and the late-stage modifications of bioactive molecules. Without aromatic aldehydes, the synthesis of 3-aryl-4-acylpyrimido[1,2- b ]indazole derivatives can also be accomplished using alternative reaction conditions.
Details
- Language :
- English
- ISSN :
- 1364-548X
- Volume :
- 60
- Issue :
- 82
- Database :
- MEDLINE
- Journal :
- Chemical communications (Cambridge, England)
- Publication Type :
- Academic Journal
- Accession number :
- 39319418
- Full Text :
- https://doi.org/10.1039/d4cc03910f