Synlett, Inhaltsverzeichnis Synlett 2020; 31(10): 1003-1006DOI: 10.1055/s-0039-1690831 letter © Georg Thieme Verlag Stuttgart · New YorkEfficient Synthesis of 4H-3,1-Benzoxazine Derivatives via One-Pot Sequential Passerini-Azide/Palladium-Catalyzed Azide–Isocyanide Coupling/Cyclization Reaction Qi-Xun Feng , Zhi-Ying Mu , Gang Yao , Jia-An Zhang , Hui-Ting He , Yong-Long Pang , Jun Xiong∗Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A new, one-pot method for the synthesis of 4H-3,1-benzoxazine derivatives has been developed. The Passerini-azide reactions of 2-azidobenzaldehydes, trimethylsilyl azide, and isocyanides produced azide intermediate without separation, which then reacted with isocyanides to give 4H-3,1-benzoxazine derivatives via a tandem one-pot palladium-catalyzed azide–isocyanide coupling/cyclization reaction in moderate to good yields. Key words Key words4H-3,1-benzoxazine derivatives - one pot - Passerini-azide reaction - palladium - azide–isocyanide coupling Volltext Referenzen References and Notes 1 These authors contributed equally. 2 Shaaban S, Negm A, Ashmawy AM, Ahmed DM, Wessjohann LA. Eur. J. Med. Chem. 2016; 122: 55 3 Ikeda Y. Thromb. Haemost. 1999; 82: 435 4 Ostrovskii VA, Trifonov RE, Popova EA. Russ. Chem. Bull., Int. Ed. 2012; 61: 768 5a Aalla S, Gilla G, Bojja Y, Anumula RR, Vummenthala PR, Padi PR. Org. Process Res. Dev. 2012; 16: 682 5b Breschi MC, Calderone V, Digiacomo M, Martelli A, Martinotti E, Minutolo F, Rapposelli S, Balsamo A. J. Med. Chem. 2004; 47: 5597 6a Zhang PW, Terefenko EA, Fensome A, Zhang ZM, Zhu Y, Cohen J, Winneker R, Wrobel J, Yardley J. Bioorg. Med. Chem. Lett. 2012; 12: 787 6b Hays SJ, Caprathe BW, Gilmore JL, Amin N, Emmerling MR, Michael W, Nadimpalli R, Nath R, Raser KJ, Stafford D, Watson D, Wang K, Jaen JC. J. Med. 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Synthesis 2018; 50: 330 23 General procedure for the one-pot preparation of 4H-3,1-benzoxazines 5: A mixture of 2-azidobenzaldehyde 1 (2 mmol), trimethylsilyl azide (2 mmol), and isocyanide 2 (2 mmol) was stirred in CH2Cl2 (10 mL) at room temperature for 3 days. After the solvent was removed under reduced pressure, THF (5 mL) was added, then isocyanide 4 (3 mmol) and Pd(PPh3)4 (0.2 mmol) were added sequentially to the reaction system, and the solution was stirred at 60 °C for 12 h. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (EtOAc/petroleum ether, 1:10) to afford product 5. 5a: Yield: 0.552 g (84%); yellow solid; mp 145–146 °C; 1H NMR (CDCl3, 600 MHz): δ = 7.26 (t, J = 8.4 Hz, 1 H), 7.07 (d, J = 7.8 Hz, 1 H), 6.89 (t, J = 7.2 Hz, 2 H), 6.46 (d, J = 7.8 Hz, 1 H), 4.40 (s, 1 H), 1.68 (s, 9 H), 1.40 (s, 9 H). 13C NMR (CDCl3, 150 MHz): δ = 151.9, 150.3, 141.8, 130.0, 123.6, 123.0, 122.7, 119.8, 70.0, 62.6, 51.5, 30.4, 29.2. LCMS (ESI): m/z [M + H]+ = 329. Anal. Calcd for C17H24N6O: C, 62.17; H, 7.37; N, 25.59. Found: C, 62.49; H, 7.81; N, 25.72. Zusatzmaterial Zusatzmaterial Supporting Information