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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
Ren,Jian; Ding,Shihua; Li,Xiaonian; Bi,Ran; Zhao,Qinshi
2021
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume86Issue:18Pages:12762-12771
AbstractA 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 alpha,beta-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(sp(3))-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.
KeywordBIOLOGICAL EVALUATION REGIOSELECTIVE SYNTHESIS CASCADE REACTIONS FUNCTIONALIZATION DEHYDROGENATION DISCOVERY POTENT BOND SAR
DOI10.1021/acs.joc.1c01343
WOS IDWOS:000697353500027
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/73013
Collection中国科学院昆明植物研究所
Affiliation1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China
Recommended Citation
GB/T 7714
Ren,Jian,Ding,Shihua,Li,Xiaonian,et al. An Approach for the Synthesis of Pyrazolo[1,5-a]pyrimidines via Cu(II)-Catalyzed [3+3] Annulation of Saturated Ketones with Aminopyrazoles[J]. JOURNAL OF ORGANIC CHEMISTRY,2021,86(18):12762-12771.
APA Ren,Jian,Ding,Shihua,Li,Xiaonian,Bi,Ran,&Zhao,Qinshi.(2021).An Approach for the Synthesis of Pyrazolo[1,5-a]pyrimidines via Cu(II)-Catalyzed [3+3] Annulation of Saturated Ketones with Aminopyrazoles.JOURNAL OF ORGANIC CHEMISTRY,86(18),12762-12771.
MLA Ren,Jian,et al."An Approach for the Synthesis of Pyrazolo[1,5-a]pyrimidines via Cu(II)-Catalyzed [3+3] Annulation of Saturated Ketones with Aminopyrazoles".JOURNAL OF ORGANIC CHEMISTRY 86.18(2021):12762-12771.
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