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Efficient Synthesis of Tetrahydropyrazolo[1,5-a]pyrimidines Based on the Recyclization of N-Arylitaconimides with Aminopyrazoles.
- Source :
-
Synthesis . Sep2024, Vol. 56 Issue 17, p2703-2708. 6p. - Publication Year :
- 2024
-
Abstract
- This article presents an efficient one-step synthesis of tetrahydropyrazolo[1,5- a ]pyrimidines through the recyclization of N -arylitaconimides with aminopyrazoles. The heterocyclic system of pyrazolo[3,4- b ]pyrimidine is known for its diverse biological properties, making its derivatives significant in pharmaceutical and medicinal chemistry. The study focuses on the regio- and chemoselective cascade reaction of N -arylitaconimides with 5-aminopyrazoles, demonstrating a new approach to synthesizing pyrazolo[1,5- a ]pyrimidines and pyrazolo[3,4- b ]pyridines. The methodology, involving boiling in isopropyl alcohol with acetic acid, yields selectively either pyrazolo[3,4- b ]pyridines or pyrazolo[1,5- a ]pyrimidines based on the substituents in the aminopyrazoles. The study elucidates the reaction mechanism, structural characterization using NMR spectroscopy, and confirms the structures via high-performance liquid chromatography and mass spectrometry. The simplicity and synthetic potential of this approach make it a valuable method for the preparation of these heterocyclic frameworks. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00397881
- Volume :
- 56
- Issue :
- 17
- Database :
- Academic Search Index
- Journal :
- Synthesis
- Publication Type :
- Academic Journal
- Accession number :
- 179020405
- Full Text :
- https://doi.org/10.1055/s-0043-1775376