Organic Letters
Organic Letters
5 years ago

Silver(I)-Catalyzed Regioselective Synthesis of Triazole Fused-1,5-Benzoxazocinones

Silver(I)-Catalyzed Regioselective Synthesis of Triazole Fused-1,5-Benzoxazocinones
Indrajeet J. Barve, Chung-Ming Sun, Tushar Ulhas Thikekar
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00907

DOI: 10.1021/acs.orglett.7b00907

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