標題: | Silver(I)-Catalyzed Regioselective Synthesis of Triazole Fused-1,5-Benzoxazocinones |
作者: | Barve, Indrajeet J. Thikekar, Tushar Ulhas Sun, Chung-Ming 應用化學系 Department of Applied Chemistry |
公開日期: | 5-五月-2017 |
摘要: | An efficient and regioselective synthesis of novel 1,2,3-triazole-fused-1,5-benzoxazocinones through intramolecular cyclization of substituted ethynyl triazoyl benzoic acids was explored. A crucial precursor 5-iodo-1,2,3-triazole benzoate was obtained from substituted 2-azido benzoic acid esters in a single step through a Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) reaction using a CuI/NBS catalytic system. A carbon carbon triple bond was installed through a Sonogashira coupling reaction by various terminal alkynes. Finally, the 1,4,5-substituted ethynyl triazoyl benzoic acids were cyclized by a AgOTf-mediated intramolecular cyclization to afford 8-endo-dig 1,2,3-triazole-fused-1,5-benzoxazocinones exclusively. |
URI: | http://dx.doi.org/10.1021/acs.orglett.7b00907 http://hdl.handle.net/11536/145486 |
ISSN: | 1523-7060 |
DOI: | 10.1021/acs.orglett.7b00907 |
期刊: | ORGANIC LETTERS |
Volume: | 19 |
起始頁: | 2370 |
結束頁: | 2373 |
顯示於類別: | 期刊論文 |