Electrochemical decarboxylative C3 alkylation of quinoxalin-2(1H)-ones with N-hydroxyphthalimide esters.

作者: Kaikai Niu , Lingyun Song , Yanke Hao , Yuxiu Liu , Qingmin Wang

DOI: 10.1039/D0CC05391K

关键词:

摘要: We have developed a protocol for electrochemical decarboxylative C3 alkylation of wide range quinoxalin-2(1H)-ones under metal- and additive-free conditions. N-Hydroxyphthalimide esters derived from chain, cyclic, primary, secondary, tertiary carboxylic acids with broad scope proved to be suitable substrates. This operationally simple performed in an undivided cell constant-current conditions is late-stage functionalization quinoxalin-2(1H)-ones. The reactions can even carried out 3 V battery as power source, which demonstrates that organic electrosynthesis accomplished without the need specialized equipment.

参考文章(67)
David S. Lawrence, Jean E. Copper, Charles D. Smith, Structure−Activity Studies of Substituted Quinoxalinones as Multiple-Drug-Resistance Antagonists Journal of Medicinal Chemistry. ,vol. 44, pp. 594- 601 ,(2001) , 10.1021/JM000282D
Alexander Buitrago Santanilla, Erik L. Regalado, Tony Pereira, Michael Shevlin, Kevin Bateman, Louis-Charles Campeau, Jonathan Schneeweis, Simon Berritt, Zhi-Cai Shi, Philippe Nantermet, Yong Liu, Roy Helmy, Christopher J. Welch, Petr Vachal, Ian W. Davies, Tim Cernak, Spencer D. Dreher, Nanomole-scale high-throughput chemistry for the synthesis of complex molecules Science. ,vol. 347, pp. 49- 53 ,(2015) , 10.1126/SCIENCE.1259203
Mai I. Shahin, Dalal A. Abou El Ella, Nasser S.M. Ismail, Khaled A.M. Abouzid, Design, synthesis and biological evaluation of type-II VEGFR-2 inhibitors based on quinoxaline scaffold. Bioorganic Chemistry. ,vol. 56, pp. 16- 26 ,(2014) , 10.1016/J.BIOORG.2014.05.010
Michel Weïwer, James Spoonamore, Jingqiang Wei, Boris Guichard, Nathan T. Ross, Kristina Masson, Whitney Silkworth, Sivaraman Dandapani, Michelle Palmer, Christina A. Scherer, Andrew M. Stern, Stuart L. Schreiber, Benito Munoz, A Potent and Selective Quinoxalinone-Based STK33 Inhibitor Does Not Show Synthetic Lethality in KRAS-Dependent Cells ACS Medicinal Chemistry Letters. ,vol. 3, pp. 1034- 1038 ,(2012) , 10.1021/ML300246R
Jeff D. Debad, Jonathan C. Morris, Philip Magnus, Allen J. Bard, Anodic Coupling of Diphenylbenzo[k]fluoranthene: Mechanistic and Kinetic Studies Utilizing Cyclic Voltammetry and Electrogenerated Chemiluminescence. Journal of Organic Chemistry. ,vol. 62, pp. 530- 537 ,(1997) , 10.1021/JO961448E
Sahar Rashidnadimi, Tsung Hsi Hung, Ken-Tsung Wong, Allen J. Bard, Electrochemistry and electrogenerated chemiluminescence of 3,6-di(spirobifluorene)-N-phenylcarbazole Journal of the American Chemical Society. ,vol. 130, pp. 634- 639 ,(2008) , 10.1021/JA076033X
Shadia A. Galal, Sarah H.M. Khairat, Fatma A.F. Ragab, Ahmed S. Abdelsamie, Mamdouh M. Ali, Salwa M. Soliman, Jérémie Mortier, Gerhard Wolber, Hoda I. El Diwani, Design, synthesis and molecular docking study of novel quinoxalin-2(1H)-ones as anti-tumor active agents with inhibition of tyrosine kinase receptor and studying their cyclooxygenase-2 activity European Journal of Medicinal Chemistry. ,vol. 86, pp. 122- 132 ,(2014) , 10.1016/J.EJMECH.2014.08.048
A. A. Kalinin, V. A. Mamedov, Synthesis of 3-alkylquinoxalin-2(1H)-ones via Grignard reaction Russian Journal of Organic Chemistry. ,vol. 45, pp. 1098- 1101 ,(2009) , 10.1134/S1070428009070185
Xiangyu Qin, Xin Hao, Hui Han, Shaojuan Zhu, Yanchun Yang, Bobin Wu, Saghir Hussain, Shagufta Parveen, Chaojun Jing, Bing Ma, Changjin Zhu, Design and Synthesis of Potent and Multifunctional Aldose Reductase Inhibitors Based on Quinoxalinones Journal of Medicinal Chemistry. ,vol. 58, pp. 1254- 1267 ,(2015) , 10.1021/JM501484B
Soňa Křupková, Petr Funk, Miroslav Soural, Jan Hlaváč, 4-Chloro-2-Fluoro-5-Nitrobenzoic Acid as a Possible Building Block for Solid-phase Synthesis of Various Heterocyclic Scaffolds ACS Combinatorial Science. ,vol. 15, pp. 20- 28 ,(2013) , 10.1021/CO300109H