A phosgene and peroxide-free one-pot tandem synthesis of isatoic anhydrides involving anthranilic acid, Boc anhydride, and 2-chloro-N-methyl pyridinium iodide

作者: Chhaya Verma , Somesh Sharma , Arunendra Pathak

DOI: 10.1016/J.TETLET.2013.10.034

关键词: PeroxideIodidePyridiniumAnthranilic acidCarbamateTandemOrganic chemistryChemistryPhosgeneIsatoic anhydride

摘要: Abstract A phosgene and peroxide-free approach for the synthesis of isatoic anhydrides has been described. The involves carbamate formation with Boc anhydride followed by in situ cyclization to afford anhydride. importance this synthetic strategy is ease operation, scalability, preparation from readily available raw materials.

参考文章(26)
M.-G. A. Shvekhgeimer, SYNTHESIS OF HETEROCYCLIC COMPOUNDS BASED ON ISATOIC ANHYDRIDES (2H-3,1-BENZOXAZINE-2,4-DIONES). (REVIEW) Chemistry of Heterocyclic Compounds. ,vol. 37, pp. 385- 443 ,(2001) , 10.1023/A:1017631318971
J. Richard Miller, Venkataraman Thanabal, Michael M. Melnick, Manjinder Lall, Charles Donovan, Ronald W. Sarver, Doh-Yeel Lee, Jeff Ohren, Don Emerson, The use of biochemical and biophysical tools for triage of high-throughput screening hits - A case study with Escherichia coli phosphopantetheine adenylyltransferase. Chemical Biology & Drug Design. ,vol. 75, pp. 444- 454 ,(2010) , 10.1111/J.1747-0285.2010.00957.X
Jing Lu Liang, So-Eun Park, Youngjoo Kwon, Yurngdong Jahng, Synthesis of benzo-annulated tryptanthrins and their biological properties. Bioorganic & Medicinal Chemistry. ,vol. 20, pp. 4962- 4967 ,(2012) , 10.1016/J.BMC.2012.06.034
Yoshio Iwakura, Keikichi Uno, Sanam Kang, The Syntheses and Some Reactions of ι-Isocyanatoalkanecarboxylic Acid Chlorides and Isocyanatobenzoyl Chlorides Journal of Organic Chemistry. ,vol. 31, pp. 142- 146 ,(1966) , 10.1021/JO01339A030
Ernst Mohr, IV. Mitteilung über die Hofmannsche Reaktion Journal Fur Praktische Chemie-chemiker-zeitung. ,vol. 73, pp. 281- 329 ,(1906) , 10.1002/PRAC.19090790117
Fouad H. Darras, Beata Kling, Jörg Heilmann, Michael Decker, Neuroprotective Tri- and Tetracyclic BChE Inhibitors Releasing Reversible Inhibitors upon Carbamate Transfer ACS Medicinal Chemistry Letters. ,vol. 3, pp. 914- 919 ,(2012) , 10.1021/ML3001825
St. Niementowski, Br. Rozański, Synthese der Isatosäure Berichte der deutschen chemischen Gesellschaft. ,vol. 22, pp. 1672- 1677 ,(1889) , 10.1002/CBER.188902201340
Ernst Erdmann, Constitution und Verhalten der „Isatosäure” European Journal of Inorganic Chemistry. ,vol. 32, pp. 2159- 2172 ,(1899) , 10.1002/CBER.189903202135
Rosanna Tedesco, Antony N. Shaw, Ramesh Bambal, Deping Chai, Nestor O. Concha, Michael G. Darcy, Dashyant Dhanak, Duke M. Fitch, Adam Gates, Warren G. Gerhardt, Dina L. Halegoua, Chao Han, Glenn A. Hofmann, Victor K. Johnston, Arun C. Kaura, Nannan Liu, Richard M. Keenan, Juili Lin-Goerke, Robert T. Sarisky, Kenneth J. Wiggall, Michael N. Zimmerman, Kevin J. Duffy, 3-(1,1-dioxo-2H-(1,2,4)-benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinones, potent inhibitors of hepatitis C virus RNA-dependent RNA polymerase. Journal of Medicinal Chemistry. ,vol. 49, pp. 971- 983 ,(2006) , 10.1021/JM050855S