Syntheses of CF2H-containing spirocyclopropyloxindoles from in situ generated CF2HCHN2 and 3-ylideneoxindoles. Issue 39 (28th September 2017)

• Record Type: Journal Article
• Authors: Han, Wen-Yong; Zhao, Jia; Wang, Jian-Shu; Cui, Bao-Dong; Wan, Nan-Wei; Chen, Yong-Zheng
• Is Part Of: Tetrahedron. Volume 73:Issue 39(2017)
• Page Start: 5806
• Page End: 5812
• Publication Date: 2017-09-28
• Subjects: Spirooxindoles -- Difluoromethyl diazomethane -- 3-Ylideneoxindoles -- Difluoromethyl group -- [3+2] cycloaddition/ring contraction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.08.022
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A facile and practical [3+2] cycloaddition/ring contraction for the construction of structurally diverse CF2 H-containing spirocyclopropyloxindoles was developed. Starting from isatin-derived 3-ylideneoxindoles and in situ generated CF2 HCHN2, the desired products were obtained in good to excellent results (up to 99% yield and >99:1 trans/cis ) in the absence of metal catalyst. The potential application of the protocol was also demonstrated by the synthesis of the CF2 H-substituted analog of HIV-1 NNRTI inhibitor. Graphical abstract: