A new synthesis of N-substituted о-trifluoroacetylanilines

作者: Alexander F. Shidlovskii , Alexander S. Golubev , Dmitrii V. Gusev , Kyrill Yu. Suponitsky , Alexander S. Peregudov

DOI: 10.1016/J.JFLUCHEM.2012.07.002

关键词:

摘要: Abstract A method for the synthesis of N-substituted о -trifluoroacetylanilines by reaction isatoic anhydrides with (trifluoromethyl)trimethylsilane (Ruppert–Prakash reagent) has been developed. This provides easy access to both N-alkyl- and N-aryl- in high yields. Cyclisation trifluoroacetic acid gives 9-trifluoromethylacridines.

参考文章(37)
Steven D. Young, Kenneth E. Rittle, James C. Barrow, Phung Le Ngo, Rowena V. Cube, Zhiqiang Yang, Quinazolinone t-type calcium channel antagonists ,(2006)
Shu-Chen Lin, Yue-Mei Zhang, Mark J. Macielag, Peter J. Connolly, Amino-pyrrolidine-azetidine diamides as monoacylglycerol lipase inhibitors ,(2011)
Goetz E. Hardtmann, Gabor Koletar, Oskar R. Pfister, THE CHEMISTRY OF 2H‐3,1‐BENZOXAZINE‐2,4(1H)DIONE (ISATOIC ANHYDRIDES) PART 1, THE SYNTHESIS OF N‐SUBSTITUTED 2H‐3,1‐BENZOXAZINE‐2,4(1H)DIONES Journal of Heterocyclic Chemistry. ,vol. 12, pp. 565- 572 ,(1975) , 10.1002/JHET.5570120325
Mona Patel, Robert J. McHugh, Beverly C. Cordova, Ronald M. Klabe, Susan Erickson-Viitanen, George L. Trainor, Soo S. Ko, Synthesis and evaluation of benzoxazinones as HIV-1 reverse transcriptase inhibitors. Analogs of Efavirenz (SUSTIVATM) Bioorganic & Medicinal Chemistry Letters. ,vol. 9, pp. 3221- 3224 ,(1999) , 10.1016/S0960-894X(99)00565-X
Takashi Mizutani, Shiho Ishikawa, Tsuyoshi Nagase, Hidekazu Takahashi, Takashi Fujimura, Takahide Sasaki, Akira Nagumo, Ken Shimamura, Yasuhisa Miyamoto, Hidefumi Kitazawa, Maki Kanesaka, Ryo Yoshimoto, Katsumi Aragane, Shigeru Tokita, Nagaaki Sato, Discovery of Novel Benzoxazinones as Potent and Orally Active Long Chain Fatty Acid Elongase 6 Inhibitors Journal of Medicinal Chemistry. ,vol. 52, pp. 7289- 7300 ,(2009) , 10.1021/JM900915X
A. S. Golubev, V. O. Bogomolov, A. F. Shidlovskii, L. G. Dezhenkova, A. S. Peregudov, A. A. Shtil, N. D. Chkanikov, Synthesis of fluoromethyl-containing analogs of antitumor alkaloid luotonin A Russian Chemical Bulletin. ,vol. 59, pp. 209- 218 ,(2010) , 10.1007/S11172-010-0064-9
Michael E. Pierce, Rodney L. Parsons, Lilian A. Radesca, Young S. Lo, Stuart Silverman, James R. Moore, Qamrul Islam, Anusuya Choudhury, Joseph M. D. Fortunak, Dieu Nguyen, Chi Luo, Susan J. Morgan, Wayne P. Davis, Pat N. Confalone, Cheng-yi Chen, Richard D. Tillyer, Lisa Frey, Lushi Tan, Feng Xu, Dalian Zhao, Andrew S. Thompson, Edward G. Corley, Edward J. J. Grabowski, Robert Reamer, Paul J. Reider, Practical asymmetric synthesis of Efavirenz (DMP 266), an HIV-1 reverse transcriptase inhibitor Journal of Organic Chemistry. ,vol. 63, pp. 8536- 8543 ,(1998) , 10.1021/JO981170L
Donald H. Aue, Darryl Thomas, Addition of dimethyl acetylenedicarboxylate to imino ethers. Trapping of a 1,4-dipolar intermediate The Journal of Organic Chemistry. ,vol. 40, pp. 2360- 2365 ,(1975) , 10.1021/JO00904A021
Mona Patel, Soo S. Ko, Robert J. McHugh, Jay A. Markwalder, Anurag S. Srivastava, Beverly C. Cordova, Ronald M. Klabe, Susan Erickson-Viitanen, George L. Trainor, Steven.P. Seitz, Synthesis and evaluation of analogs of Efavirenz (SUSTIVATM) as HIV-1 reverse transcriptase inhibitors Bioorganic & Medicinal Chemistry Letters. ,vol. 9, pp. 2805- 2810 ,(1999) , 10.1016/S0960-894X(99)00486-2