3‐Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of ortho‐Functionalized Cinnamic Esters
作者： Slim Chaabouni , Florent Simonet , Alison François , Souhir Abid , Chantal Galaup
关键词: Combinatorial chemistry 、 Organic chemistry 、 Regioselectivity 、 Cascade reaction 、 Trifluoromethylation 、 Chemistry 、 Reagent
摘要: A method for the trifluoromethylation of ortho-hydroxycinnamic esters was developed to achieve regioselective synthesis 3-trifluoromethylated coumarins. The reaction performed by using Togni reagent as CF3 source under mild conditions and showed good functional- group tolerance. scope this copper-mediated further expanded carbostyrils starting from ortho-aminocinnamic derivatives. Interestingly, a sequential one-pot coumarins salicylaldehydes developed. mechanism cascade explored, radical pathway found be consistent with obtained results.
sci-hub.se 参考文章(65)
Kuldipsinh P. Barot, Shailesh V. Jain, Laurent Kremer, Shubhra Singh, Manjunath D. Ghate, Recent advances and therapeutic journey of coumarins: current status and perspectives Medicinal Chemistry Research. ,vol. 24, pp. 2771- 2798 ,(2015) , 10.1007/S00044-015-1350-8
Toshihiko Tashima, The structural use of carbostyril in physiologically active substances Bioorganic & Medicinal Chemistry Letters. ,vol. 25, pp. 3415- 3419 ,(2015) , 10.1016/J.BMCL.2015.06.027
Stephen Tyndall, Koon Fai Wong, Melissa A. VanAlstine-Parris, Insight into the Mechanism of the Pechmann Condensation Reaction Using NMR. Journal of Organic Chemistry. ,vol. 80, pp. 8951- 8953 ,(2015) , 10.1021/ACS.JOC.5B01802
Iwao Ojima, Fluorine in medicinal chemistry and chemical biology Wiley. ,(2009) , 10.1002/9781444312096
Xiaodan Zhang, Ping Huang, Yaming Li, Chunying Duan, A mild and fast continuous-flow trifluoromethylation of coumarins with the CF3 radical derived from CF3SO2Na and TBHP Organic and Biomolecular Chemistry. ,vol. 13, pp. 10917- 10922 ,(2015) , 10.1039/C5OB01516B
Sonali Sandhu, Yogita Bansal, Om Silakari, Gulshan Bansal, Coumarin hybrids as novel therapeutic agents. Bioorganic & Medicinal Chemistry. ,vol. 22, pp. 3806- 3814 ,(2014) , 10.1016/J.BMC.2014.05.032
Jagdeep Grover, Sanjay M. Jachak, Coumarins as privileged scaffold for anti-inflammatory drug development RSC Advances. ,vol. 5, pp. 38892- 38905 ,(2015) , 10.1039/C5RA05643H
K. Muller, C. Faeh, F. Diederich, Fluorine in Pharmaceuticals: Looking Beyond Intuition. Science. ,vol. 317, pp. 1881- 1886 ,(2007) , 10.1126/SCIENCE.1131943
Ronald L. Atkins, Dan E. Bliss, Substituted coumarins and azacoumarins. Synthesis and fluorescent properties Journal of Organic Chemistry. ,vol. 43, pp. 1975- 1980 ,(1978) , 10.1021/JO00404A028
Narender Reddy Emmadi, Krishnaiah Atmakur, Madhu Chennapuram, Jagadeesh Babu Nanubolu, Synthesis of amidoalkyl chromen-2-ones by one pot three component reaction under solvent free conditions RSC Advances. ,vol. 4, pp. 14501- 14506 ,(2014) , 10.1039/C4RA00166D