期刊
TETRAHEDRON
卷 73, 期 39, 页码 5806-5812出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.08.022
关键词
Spirooxindoles; Difluoromethyl diazomethane; 3-Ylideneoxindoles; Difluoromethyl group; [3+2] cycloaddition/ring contraction
资金
- Science and Technology Department of Guizhou Province [QKHJZ-2015-2155, QKHRC-2016-4029, QKHPTRC-2016-5801, QKHRCTD-2014-4002]
- Program for the Top Talents of Science and Technology in Higher Learning Institutions of Guizhou Province [QJHKYZ-2016-081]
- Education Department of Guizhou Province [QJHRCTDZ-2012-03]
- Ministry of Education [NCET-13-1069]
- Zunyi Medical University [F-737]
A facile and practical [3+2] cycloaddition/ring contraction for the construction of structurally diverse CF2H-containing spirocyclopropyloxindoles was developed. Starting from isatin-derived 3-ylideneoxindoles and in situ generated CF2HCHN2, 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 CF2H-substituted analog of HIV-1 NNRTI inhibitor. (c) 2017 Elsevier Ltd. All rights reserved.
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