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Domino synthesis of 5-aminoimidazoles from Strecker multicomponent adducts via ytterbium-promoted isocyanide insertion/5-exo-dig cyclization.
- Source :
-
Molecular diversity [Mol Divers] 2023 Feb; Vol. 27 (1), pp. 511-515. Date of Electronic Publication: 2022 Apr 13. - Publication Year :
- 2023
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Abstract
- A new Lewis acid promoted domino isocyanide insertion/5-exo-dig cyclization of readily available Strecker 3-component adducts to 4-substituted 5-aminoimidazole derivatives is herein reported. Despite their potential as relevant heterocyclic scaffolds in medicinal chemistry programs, this class of compounds is still underrepresented, with current synthetic strategies poorly efficient in terms of timing and yields. To this end, we show how the exploitation of unconventional reactivities of isocyanides, promoted by ytterbium-triflate, could represent a key resource to enable a fast and easy access to such an unexplored area of the chemical space.<br /> (© 2022. The Author(s), under exclusive licence to Springer Nature Switzerland AG.)
- Subjects :
- Cyclization
Imidazoles chemistry
Cyanides chemistry
Ytterbium
Subjects
Details
- Language :
- English
- ISSN :
- 1573-501X
- Volume :
- 27
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Molecular diversity
- Publication Type :
- Academic Journal
- Accession number :
- 35416620
- Full Text :
- https://doi.org/10.1007/s11030-022-10418-4