TY - JOUR
T1 - Silver(I)-Catalyzed Regioselective Synthesis of Triazole Fused-1,5-Benzoxazocinones
AU - Barve, Indrajeet J.
AU - Thikekar, Tushar Ulhas
AU - Sun, Chung-Ming
PY - 2017/5/5
Y1 - 2017/5/5
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85019026258&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.7b00907
DO - 10.1021/acs.orglett.7b00907
M3 - Article
C2 - 28409630
AN - SCOPUS:85019026258
SN - 1523-7060
VL - 19
SP - 2370
EP - 2373
JO - Organic Letters
JF - Organic Letters
IS - 9
ER -