Radical Three-Component Nitro Spiro-Cyclization of Unsaturated Sulfonamides/Amides to Access NO<sub>2</sub>-Featured 4-Azaspiro[4.5]decanes
Changyou Guo, Li‐Jun Li, Qinqin Yan, Jingyi Chen, Zhong‐Quan Liu, Quanxin Li, Shao‐Fei Ni, Zejiang Li
Abstract
Free radical three-component nitration/spirocyclization of unsaturated sulfonamides/amides with tert -butyl nitrite was developed for the construction of diverse NO 2 -revised 4-azaspiro[4.5]decanes. This tandem system featured metal-free participation, simple operation, good selectivity/yields, and a green/low-cost O source. Meanwhile, one nitro-containing complex molecule and a scaled-up operation were performed well to test the synthetic potential of the cascade reaction. Isotopic labeling, radical inhibition experiments, and DFT analysis were carried out to gain insight into the reaction process.
Topics & Concepts
ChemistryNitroComponent (thermodynamics)Medicinal chemistryCombinatorial chemistryOrganic chemistryThermodynamicsAlkylPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques