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-May-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
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