Synthesis, Table of Contents Synthesis 2023; 55(19): 3179-3185DOI: 10.1055/a-2110-1989 paper Method for the Synthesis of 2H-1,4-Benzoxazin-3-(4H)-ones via Ligand-Free Copper-Catalyzed Cascade Reaction Authors Lingyu Zhang Songlin Zhang∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract An efficient method for the synthesis of 2H-1,4-benzoxazin-3-(4H)-ones via ligand-free copper-catalyzed cascade reaction of substituted chloroacetamides with 2-halophenols has been developed for the first time. Some of the issues typically encountered during the synthesis of 2H-1,4-benzoxazin-3-(4H)-ones, including adding noble metals and ligands, poor substrate scope, have been addressed using this newly developed ligand-free copper-catalyzed cascade reaction. Key words Key wordscopper - cross-coupling - ligand-free - Ullmann reaction - 2H-1,4-benzoxazin-3-(4H)-ones Full Text References References 1a Landquist JK. In Comprehensive Heterocyclic Chemistry, Vol. 1. Katritzky AR, Rees CW. Pergamon; New York: 1984: 166 1b Crowley PJ. In Comprehensive Heterocyclic Chemistry, Vol. 1, Chap. 1.07. Katritzky AR, Rees CW. Pergamon; New York: 1984 1c Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451 1d DeSimone RW, Currie KS, Mitchell SA, Darrow JW, Pippin DA. Comb. Chem. High Throughput Screening 2004; 7: 473 2 Foto E, Özen Ç, Zilifdar F, Tekiner-Gülbaş B, Yıldız İ, Akı-Yalçın E, Diril N, Yalçın İ. DARU J. Pharm. Sci. 2020; 28: 65 3 Frechette R, Weidner-Wells MA. WO Patent Appl. 9717333, 1997 4 Duke SO, Lydon J, Becerril JM, Sherman TD, Lehnen LP, Matsumoto H. Weed Sci. 1991; 39: 465 5 Caliendo G, Grieco P, Perissutti E, Santagada V, Santini A, Albrizio S, Fattorusso C, Pinto A, Sorrentino R. Eur. J. Med. Chem. 1998; 33: 957 6a Caliendo G, Perissutti E, Santagada V, Fiorino F, Severino B, Cirillo D, d’Emmanuele di Villa Bianca R, Lippolis L, Pinto A, Sorrentino R. Eur. J. Med. Chem. 2004; 39: 815 6b Kuroita T, Marubayashi N, Sano M, Kanzaki K, Inaba K, Kawakita T. Chem. Pharm. Bull. 1996; 44: 2051 6c Shridhar DR, Jogibhukta M, Krishnan VS. H. Org. Prep. Proced. Int. 1982; 14: 195 6d Henry N, Guillaumet G, Pujol MD. Tetrahedron Lett. 2004; 45: 1465 6e Nagarapu L, Ravirala N. Heterocycl. Commun. 2000; 6: 515 7a Rybczynski PJ, Zeck RE, Dudash J, Combs DW, Burris TP, Yang M, Osborne MC, Chen XK, Demarest T. J. Med. Chem. 2004; 47: 196 7b Arrault A, Touzeau F, Guillaumet G, Leger J.-M, Jarry C, Merour J.-Y. Tetrahedron 2002; 58: 8145 7c Armitage M, Bret G, Choudary BM, Kingswood M, Loft M, Moore S, Smith S, Urquhart MW. J. Org. Process Res. Dev. 2012; 16: 1626 7d Ramesh C, Raju BR, Kavala V, Kuo C.-W, Yao C.-F. Tetrahedron 2011; 67: 1187 7e Rajitha C, Dubey PK, Sunku V, Piedrafita FJ, Veeramaneni VR, Pal M. Eur. J. Med. Chem. 2011; 46: 4887 8a Dai WM, Wang X, Ma C. Tetrahedron 2005; 61: 6879 8b Zuo H, Meng L, Ghate M, Hwang K.-H, Cho YK, Chandrasekhar S, Reddy ChR, Shin DS. Tetrahedron Lett. 2008; 49: 3827 8c Feng G, Wu J, Dai W.-M. Tetrahedron 2006; 62: 4635 8d Xing X, Wu J, Feng G, Dai W.-M. Tetrahedron 2006; 62: 6774 9 Lee CL, Chan KP, Lam Y, Lee SY. Tetrahedron Lett. 2001; 42: 1167 10a Guram AS, Rennels RA, Buchwald SL. Angew. Chem. Int. Ed. 1995; 34: 1348 10b Louie J, Hartwig JF. Tetrahedron Lett. 1995; 36: 3609 10c Mesganaw T, Garg NK. Org. Process Res. Dev. 2013; 17: 29 10d Bhaktala S, Ghosh T. Eur. J. Org. Chem. 2021; 29: 4201 11a Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400 11b Beletskaya IP, Cheprakov AV. Coord. Chem. Rev. 2004; 248: 2337 11c Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2017; 56: 16136 11d Baqi Y. Catalysts 2021; 11: 46 11e Chen D, Bao W. Adv. Synth. Catal. 2010; 352: 955 11f Xu H, Wolf C. Chem. Commun. 2009; 1715 11g Liu X, Zhang S. Synlett 2011; 1137 11h Liu X, Zhang S. Synlett 2011; 268 11i Zhang S, Liu X, Wang T. Adv. Synth. Catal. 2011; 353: 1463 12a Yin F, Feng G, Song Q, Qi C. J. Chem. Res. 2012; 36: 41 12b Feng G, Chen F, Song Q, Qi CA. Synlett 2012; 23: 601 12c Xu Z, Li K, Zhai R, Liang T, Gui X, Zhang R. RSC Adv. 2017; 7: 51972 13a Chen D, Shen G, Bao W. Org. Biomol. Chem. 2009; 7: 4067 13b Feng E, Huang H, Zhaou Y, Ye D, Jiang H, Liu H. J. Org. Chem. 2009; 74: 2846 14a Rui X, Wang C, Si D, Hui X, Li K, Wen H, Li W, Liu J. J. Org. Chem. 2021; 86: 6622 14b Zhang H, Cai Q, Ma D. J. Org. Chem. 2005; 70: 5164 14c Kondratov SA, Shein SM. Zh. Org. Khim. 1979; 15: 2160 14d Paine AJ. J. Am. Chem. Soc. 1987; 109: 1496 14e Ma X, Davies RP. Adv. Synth. Catal. 2022; 364: 2023 14f Weingarten H. J. Am. Chem. Soc. 1964; 29: 3624 15 Zhang LM, Si XJ, Rominger F, Hashmi AS. K. J. Am. Chem. Soc. 2020; 142: 10485 16 Damratha M, Caspersa LD, Duvinageb D, Nachtsheim BJ. Org. Lett. 2022; 54: 2562 17 Baraldi PG, Preti D, Tabrizi M, Fruttarolo F, Saponaro G, Baraldi S, Romagnoli R, Moorman A, Gessi S, Varanib K, Boreab P. Bioorg. Med. Chem. 2007; 15: 2514 18 Gunnlaugsson T, Brougham DF, Fanning A.-M, Nieuwenhuyzen M, O’Brien JE, Viguier R. Org. Lett. 2004; 6: 4805 19 Ramesh C, Raju BR, Kavala V, Kuo C.-W, Yao C.-F. Tetrahedron 2011; 67: 1187 20 Hashimoto Y, Ishizaki T, Shudo K, Okamoto T. Chem. Pharm. Bull. 1983; 31: 3891 21 Rekowski MW, Pyriochou A, Papapetropoulos N, Stößel A, Papapetropoulos A, Giannis A. Bioorg. Med. Chem. 2010; 18: 1288 22 Cao H, Zhu G, Sun L, Chen G, Ma X, Luo X, Zhu J. Eur. J. Med. Chem. 2019; 183: 111694 23 Zamani L, Khabnadideh S, Zomorodian K, Sakhteman A, Gholami A, Rezaei Z, Mehdipoor A, Dehkordi ME, Mortazavi R, Ghafari S. Polycycl. Aromat. Compd. 2019; 41: 347 24 Zhou J.-Z, Li Z.-B, Yang H, He X.-Y, Wang L.-Y, Tian X, Lv T.-T, Zuo H. Chem. Asian J. 2011; 23: 2947 Supplementary Material Supplementary Material Supporting Information (PDF)
