Synthetic access to isoxazoline-functionalized isoquinolines via microwave-assisted iminoxyl radical-participated cascade cyclization of vinyl isocyanides. Issue 27 (27th June 2018)

• Record Type: Journal Article
• Authors: Xu, Yulong; Chen, Hao; Li, Wei; Xie, Qiong; Yu, Linqian; Shao, Liming
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 27(2018)
• Page Start: 4996
• Page End: 5005
• Publication Date: 2018-06-27
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01229f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The synthesis of isoxazoline-functionalized isoquinolines via radical cascade cyclization of vinyl isocyanides with β, γ-unsaturated ketoximes has been described. Abstract : A convenient microwave-assisted method for the synthesis of isoxazoline-functionalized isoquinolines via the n -Bu4 NI (TBAI) catalyzed radical cascade cyclization of vinyl isocyanides with β, γ-unsaturated ketoximes has been described. The methodology presented here achieves a wide substrate scope and good to excellent yields. A radical mechanism is proposed, which is supported by the intermolecular competing kinetic isotope effect (KIE) experiment and the radical trapping experiment.