A mild two-step propargylation of aromatic bioactive small molecules

作者: Naoki Kanoh , Toshitaka Okamura , Takahiro Suzuki , Yoshiharu Iwabuchi

DOI: 10.1039/C7OB01587A

关键词:

摘要: A two-step method for introducing a propargyl group in aromatic bioactive small molecules has been developed. This features propargylation of groups using cationic hexacarbonyl complex the presence cesium carbonate, and decomplexation resultant cobalt complexes 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate. These reactions proceed under mild conditions, thus are applicable acid- and/or oxidant-sensitive molecules.

参考文章(32)
Anthony J. Atkin, Sophie Williams, Philip Sawle, Roberto Motterlini, Jason M. Lynam, Ian J. S. Fairlamb, μ2-Alkyne dicobalt(0)hexacarbonyl complexes as carbon monoxide-releasing molecules (CO-RMs): probing the release mechanism Dalton Transactions. pp. 3653- 3656 ,(2009) , 10.1039/B904627P
Richard E. Connor, Kenneth M. Nicholas, Isolation, characterization, and stability of α-[(ethynyl)dicobalt hexacarbonyl] carbonium ions Journal of Organometallic Chemistry. ,vol. 125, ,(1977) , 10.1016/S0022-328X(00)89454-1
Takumichi Sugihara, Hitoshi Ban, Masahiko Yamaguchi, Novel decomplexation method for alkyne-Co2(CO)6 complexes Journal of Organometallic Chemistry. ,vol. 554, pp. 163- 166 ,(1998) , 10.1016/S0022-328X(97)00679-7
Michael A Mercadante, Christopher B Kelly, James M Bobbitt, Leon J Tilley, Nicholas E Leadbeater, Synthesis of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate and 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl and their use in oxidative reactions Nature Protocols. ,vol. 8, pp. 666- 676 ,(2013) , 10.1038/NPROT.2013.028
Omar Robles, Daniel Romo, Chemo- and site-selective derivatizations of natural products enabling biological studies. Natural Product Reports. ,vol. 31, pp. 318- 334 ,(2014) , 10.1039/C3NP70087A
Naoki Kanoh, Takemichi Nakamura, Kaori Honda, Hiroyuki Yamakoshi, Yoshiharu Iwabuchi, Hiroyuki Osada, Distribution of photo-cross-linked products from 3-aryl-3-trifluoromethyldiazirines and alcohols Tetrahedron. ,vol. 64, pp. 5692- 5698 ,(2008) , 10.1016/J.TET.2008.04.031
Naoki Kanoh, Takahiro Suzuki, Makoto Kawatani, Yasuhiro Katou, Hiroyuki Osada, Yoshiharu Iwabuchi, Dual Structure–Activity Relationship of Osteoclastogenesis Inhibitor Methyl Gerfelin Based on TEG Scanning Bioconjugate Chemistry. ,vol. 24, pp. 44- 52 ,(2013) , 10.1021/BC3003666
Almar F Palonpon, Jun Ando, Hiroyuki Yamakoshi, Kosuke Dodo, Mikiko Sodeoka, Satoshi Kawata, Katsumasa Fujita, Raman and SERS microscopy for molecular imaging of live cells. Nature Protocols. ,vol. 8, pp. 677- 692 ,(2013) , 10.1038/NPROT.2013.030
Oliver Kuhn, Doris Rau, Herbert Mayr, How Electrophilic Are Cobalt Carbonyl Stabilized Propargylium Ions Journal of the American Chemical Society. ,vol. 120, pp. 900- 907 ,(1998) , 10.1021/JA9726264
Zhengqiu Li, Piliang Hao, Lin Li, Chelsea YJ Tan, Xiamin Cheng, Grace YJ Chen, Siu Kwan Sze, Han‐Ming Shen, Shao Q Yao, None, Design and Synthesis of Minimalist Terminal Alkyne-Containing Diazirine Photo-Crosslinkers and Their Incorporation into Kinase Inhibitors for Cell- and Tissue-Based Proteome Profiling Angewandte Chemie. ,vol. 52, pp. 8551- 8556 ,(2013) , 10.1002/ANIE.201300683