Solvent-Controlled Divergent Cyclization of 3-Ylideneoxindoles with Ethyl 2-Diazoacetate: Access to Spirocyclopropyl and Spiropyrazolines Oxindoles.

Autor: Xie DX; School of Chemistry and Chemical Engineering, Guangzhou University, 230 Wai Huan Xi Road, Guangzhou, 510006, China., Huang YM; School of Chemistry and Chemical Engineering, Guangzhou University, 230 Wai Huan Xi Road, Guangzhou, 510006, China., Lin XM; School of Chemistry and Chemical Engineering, Guangzhou University, 230 Wai Huan Xi Road, Guangzhou, 510006, China., Kang ZH; Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica Chinese Academy of Sciences, Zhongshan, 528400, China., Ni CC; School of Chemistry and Chemical Engineering, Guangzhou University, 230 Wai Huan Xi Road, Guangzhou, 510006, China., Fu YT; School of Chemistry and Chemical Engineering, Guangzhou University, 230 Wai Huan Xi Road, Guangzhou, 510006, China., Ren Z; College of Pharmacy, Shenzhen Technology University, 3002 Lantian Road, Shenzhen, 518118, China., Liu YL; School of Chemistry and Chemical Engineering, Guangzhou University, 230 Wai Huan Xi Road, Guangzhou, 510006, China.; Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Dec 10; Vol. 30 (69), pp. e202402654. Date of Electronic Publication: 2024 Oct 29.
DOI: 10.1002/chem.202402654
Abstrakt: Herein a catalyst-free solvent-controlled method for the divergent synthesis of spirocyclopropyl and spiropyrazoline oxindoles from 3-ylideneoxindoles and ethyl diazoacetate was developed. With ClCH 2 CH 2 Cl as the solvent, spirocyclopropyl oxindoles were obtained in moderate to excellent yields, whereas the use of MeOH as solvent afforded spiropyrazoline oxindoles in moderate to good yields. The readily available substrates, simple operation and various product transformations further highlighted the utility of this method.
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Databáze: MEDLINE