title: Metal-Free Ring-Expansion Reaction of Six-membered Sulfonylimines with Diazomethanes: An Approach toward Seven-Membered Enesulfonamides.
abstract: A new metal-free, ring-expansion reaction of six-membered N-sulfonylimines with unstable diazomethanes, generated in situ from the N-tosylhydrazones, has been developed. This reaction delivers valuable seven-membered enesulfonamides by a Tiffeneau-Demjanov rearrangement and intramolecular proton transfer tautomerization process. Moreover, this ring-expansion reaction can be carried out in a one-pot fashion and scaled up to the gram scale by using aryl aldehydes, without the need to isolate the N-tosylhydrazone.
authors.affiliation: Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province/College of Chemistry & Chemical Engineering, Collaborative Innovation Center of Tissue Repair Material of Sichuan Province, China West Normal University, Nanchong, 637009, China.
authors.forename: An-Jie
authors.initials: AJ
authors.lastname: Xia
authors.affiliation: Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province/College of Chemistry & Chemical Engineering, Collaborative Innovation Center of Tissue Repair Material of Sichuan Province, China West Normal University, Nanchong, 637009, China. kangtairan@sina.com.|State Key Laboratory of Biotherapy/Collaborative Innovation Center of Biotherapy, Cancer Center, West China Hospital, Sichuan University, Chengdu, P.R. China. kangtairan@sina.com.
authors.forename: Tai-Ran
authors.initials: TR
authors.lastname: Kang
authors.affiliation: Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province/College of Chemistry & Chemical Engineering, Collaborative Innovation Center of Tissue Repair Material of Sichuan Province, China West Normal University, Nanchong, 637009, China. longhe@cwnu.edu.cn.
authors.forename: Long
authors.initials: L
authors.lastname: He
authors.affiliation: Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province/College of Chemistry & Chemical Engineering, Collaborative Innovation Center of Tissue Repair Material of Sichuan Province, China West Normal University, Nanchong, 637009, China.
authors.forename: Lian-Mei
authors.initials: LM
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Biotherapy/Collaborative Innovation Center of Biotherapy, Cancer Center, West China Hospital, Sichuan University, Chengdu, P.R. China.
authors.forename: Wen-Ting
authors.initials: WT
authors.lastname: Li
authors.affiliation: State Key Laboratory of Biotherapy/Collaborative Innovation Center of Biotherapy, Cancer Center, West China Hospital, Sichuan University, Chengdu, P.R. China. jlyang01@163.com.
authors.forename: Jin-Liang
authors.initials: JL
authors.lastname: Yang
authors.affiliation: Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province/College of Chemistry & Chemical Engineering, Collaborative Innovation Center of Tissue Repair Material of Sichuan Province, China West Normal University, Nanchong, 637009, China. quanzhongliu@sohu.com.
authors.forename: Quan-Zhong
authors.initials: QZ
authors.lastname: Liu
mesh_terms: D003500:Cyclization; D003978:Diazomethane / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D007097:Imines; D008670:Metals; D013449:Sulfonamides; D003978:Diazomethane
keywords: diazo compounds; heterocycles; hydrazones; rearrangements; ring expansion