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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Electrochemical Dearomative Spirocyclization of N-Acyl Thiophene-2-sulfonamides
Zhaojiang Shi1, Wei-Zhen Wang1, Nan Li1
1Institute of Pharmaceutical Science and Technology, College of Chemistry, Fuzhou University, Fuzhou 350108, China.
Abstract:
The Friedel-Crafts type alkylation of C2-tethered thiophenes has been reported to be nonregioselective. Taking advantage of the highly regioselective 5-exo-trig spirocyclization of an electrochemically generated amidyl radical, we have unraveled an electrochemical dearomative spirocyclization of N-acyl thiophene-2-sulfonamides. Various nucleophilic agents, including carboxylates, alcohols, and fluoride, are readily incorporated to afford the remotely functionalized spirocyclic dihydrothiophenes, and their novel spirocyclic scaffolds have been shown to exhibit promising antitumor activities.
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