Photomediated Spirocyclization of <i>N</i>-Benzyl Propiolamide with <i>N</i>-Iodosuccinimide for Access to Azaspiro[4.5]deca-6,9-diene-3,8-dione
Man Yang, Jiawei Hua, Hao Wang, Tao Ma, Chengkou Liu, Wei He, Ning Zhu, Yujing Hu, Zheng Fang, Kai Guo
Abstract
A metal- and oxidant-free route for affording azaspiro[4.5]deca-6,9-diene-3,8-dione via photomediated iodinated spirocyclization of N-(4-methoxybenzyl) propiolamide has been developed. The reaction underwent a radical addition/ipso-cyclization/dearomatization process at room temperature and successfully constructed C–C and C–I bonds. This green and convenient approach could be generally expanded to produce a range of iodinated spirocyclization products in moderate to good yields.
Topics & Concepts
Deca-DieneChemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryNatural rubberOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsAlkaloids: synthesis and pharmacology