One-Pot Synthesis of N-Aryl-Nicotinamides and Diarylamines Based on a Tunable Smiles Rearrangement

作者: Shihui Liu , Shaofan Zhu , Ying Wu , Jiayu Gao , Pengfei Qian

DOI: 10.1002/EJOC.201500222

关键词:

摘要: A one-pot Smiles rearrangement has been developed as a useful protocol for the straightforward synthesis of diverse N-aryl-nicotinamides. This method also provides chemoselective access toward diarylamines based on different substitutions amide group. The potential application transformation is exemplified by an on-market succinate dehydrogenase inhibitor, boscalid.

参考文章(57)
Constance Delaugerre, Jade Ghosn, Marie-Laure Chaix, HIV-1 resistance to first- and second-generation non-nucleoside reverse transcriptase inhibitors. Aids Reviews. ,vol. 11, pp. 165- 173 ,(2009)
Niranjan Panda, Raghavender Mothkuri, Dinesh Kumar Nayak, Copper‐Catalyzed Regioselective Synthesis of N‐Aryl Amides from Aldoximes and Aryl Halides European Journal of Organic Chemistry. ,vol. 2014, pp. 1602- 1605 ,(2014) , 10.1002/EJOC.201301868
Ly Dieu Tran, Ilya Popov, Olafs Daugulis, Copper-Promoted Sulfenylation of sp2 C–H Bonds Journal of the American Chemical Society. ,vol. 134, pp. 18237- 18240 ,(2012) , 10.1021/JA3092278
Oana-Irina Patriciu, Adriana-Luminita Fînaru, Stephane Massip, Jean-Michel Leger, Christian Jarry, Gerald Guillaumet, None, Smiles rearrangement as a tool for the preparation of dihydrodipyridopyrazines. Organic Letters. ,vol. 11, pp. 5502- 5505 ,(2009) , 10.1021/OL902369V
Laurent El Kaim, Laurence Grimaud, Xavier F. Le Goff, Aurélie Schiltz, Smiles cascades toward heterocyclic scaffolds. Organic Letters. ,vol. 13, pp. 534- 536 ,(2011) , 10.1021/OL1028817
I. Mallik, S. Arabiat, J. S. Pasche, M. D. Bolton, J. S. Patel, N. C. Gudmestad, Molecular Characterization and Detection of Mutations Associated With Resistance to Succinate Dehydrogenase-Inhibiting Fungicides in Alternaria Solani Phytopathology. ,vol. 104, pp. 40- 49 ,(2014) , 10.1094/PHYTO-02-13-0041-R
Huimin Cheng, Yu Chang, Lianwen Zhang, Jinfeng Luo, Zhengchao Tu, Xiaoyun Lu, Qingwen Zhang, Jibu Lu, Xiaomei Ren, Ke Ding, Identification and optimization of new dual inhibitors of B-Raf and epidermal growth factor receptor kinases for overcoming resistance against vemurafenib. Journal of Medicinal Chemistry. ,vol. 57, pp. 2692- 2703 ,(2014) , 10.1021/JM500007H
Jinbao Xiang, Lianyou Zheng, Hongxiang Xie, Xiaowei Hu, Qun Dang, Xu Bai, Pyrrolo-dihydropteridines via a cascade reaction consisting of iminium cyclization and O–N Smiles rearrangement Tetrahedron. ,vol. 64, pp. 9101- 9107 ,(2008) , 10.1016/J.TET.2008.07.002
Xiaoyi Niu, Bingchuan Yang, Yanqiu Li, Shuai Fang, Zixiao Huang, Caixia Xie, Chen Ma, A transition metal-free tandem process to pyridazinopyrido[3,2-f][1,4]thiazepine-diones via Smiles rearrangement Organic and Biomolecular Chemistry. ,vol. 11, pp. 4102- 4108 ,(2013) , 10.1039/C3OB40719E
Gerald Pratsch, Tina Wallaschkowski, Markus R. Heinrich, The Gomberg-Bachmann reaction for the arylation of anilines with aryl diazotates. Chemistry: A European Journal. ,vol. 18, pp. 11555- 11559 ,(2012) , 10.1002/CHEM.201200430