I2–DMSO-Mediated Multicomponent [2+1+1+1] Annulation Reaction via Ethyl Nitroacetate C—NO2 Bond Cleavage as a C1 Synthon: A Route to Multisubstituted β-Pyrrolidinones Derivatives with a Quaternary Center
Zhi-Cheng Yu , Xi Shen , You Zhou , Xiang-Long Chen , Li-Sheng Wang , Yan-Dong Wu , An-Xin Wu
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (17) : 2029 -2034.
I2–DMSO-Mediated Multicomponent [2+1+1+1] Annulation Reaction via Ethyl Nitroacetate C—NO2 Bond Cleavage as a C1 Synthon: A Route to Multisubstituted β-Pyrrolidinones Derivatives with a Quaternary Center
A [2 + 1 + 1 + 1] cyclization reaction has been developed for the synthesis of multisubstituted β-pyrrolidinones from commercially available aryl methyl ketones, primary amines, and ethyl nitroacetate. In this I 2–DMSO-meditated process, the C—NO 2 bond of ethyl nitroacetate is cleaved, affording a C1 synthon, and the formation of two C—C and two C—N bonds and a quaternary carbon center are constructed in one pot. This method has good substrate compatibility and permits the late-stage modification of pharmaceutical compounds.
Cyclization / Multisubstituted β-pyrrolidinones / I 2–DMSO / C1 building blocks / Quaternary carbon center / Late-stage modification / Cracking
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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