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An Approach for the Synthesis of Pyrazolo[1,5-a]pyrimidines via Cu(II)-Catalyzed [3+3] Annulation of Saturated Ketones with Aminopyrazoles. 2021

Jian Ren, and Shihua Ding, and Xiaonian Li, and Ran Bi, and Qinshi Zhao
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.

A one-step synthesis of diversely substituted pyrazolo[1,5-a]pyrimidines from saturated ketones and 3-aminopyrazoles is presented. This transformation involves the in situ formation of α,β-unsaturated ketones via a radical process, followed by [3+3] annulation with 3-aminopyrazoles in one pot. Mechanistic studies have shown that the dual C(sp3)-H bond functionalization of inactive ketones is required for the formation of the title compounds. Notably, this dehydrogenative coupling process provides access to a host of functionalized pyrazolo[1,5-a]pyrimidines with antitumor potential from commercially available substrates.

UI MeSH Term Description Entries
D007659 Ketones Organic compounds containing a carbonyl group Ketone
D011743 Pyrimidines A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nucleic acid constituents (CYTOSINE; THYMINE; and URACIL) and form the basic structure of the barbiturates.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D055585 Physical Phenomena The entities of matter and energy, and the processes, principles, properties, and relationships describing their nature and interactions. Physical Concepts,Physical Processes,Physical Phenomenon,Physical Process,Concept, Physical,Concepts, Physical,Phenomena, Physical,Phenomenon, Physical,Physical Concept,Process, Physical,Processes, Physical

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