Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Download PDF
Synlett 2020; 31(10): 1003-1006
DOI: 10.1055/s-0039-1690831
DOI: 10.1055/s-0039-1690831
letter
Efficient Synthesis of 4H-3,1-Benzoxazine Derivatives via One-Pot Sequential Passerini-Azide/Palladium-Catalyzed Azide–Isocyanide Coupling/Cyclization Reaction
This research is funded by a Research Project of Hubei Provincial Department of Education (No. Q20192806) and by a Doctoral Research Fund of Hubei University of Science and Technology (No. BK201808).
Further Information
Publication History
Received: 14 January 2020
Accepted after revision: 02 February 2020
Publication Date:
18 February 2020 (online)
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
4H-3,1-benzoxazine derivatives - one pot - Passerini-azide reaction - palladium - azide–isocyanide couplingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690831.
- Supporting Information
-
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. Chem. 1998; 41: 1060
- 6c Kern JC, Terefenko EA, Fensome A, Unwallla R, Wrobel J, Zhu Y, Cohen J, Winneker R, Zhang Z, Zhang PW. Bioorg. Med. Chem. Lett. 2007; 17: 189
- 7 Sugiyama H, Hosoda K, Kumagai Y, Takeuchi M, Okada M. US Patent No. US4596801, 1986
- 8 Kuch H, Schmitt K, Seidl G, Hoffmann I. US Patent No. US3725404, 1973
- 9a Fensome A, Bender R, Chopra R, Cohen J, Collins MA, Hudak V, Malakian K, Lockhead S, Olland A, Svenson K, Terefenko EA, Unwalla RJ, Wilhelm JM, Wolfrom S, Zhu Y, Zhang Z, Zhang P, Winneker RC, Wrobel J. J. Med. Chem. 2005; 48: 5092
- 9b Dias N, Goossens JF, Baldeyrou B, Lansiaux A, Colson P, Di Salvo A, Bernal J, Turnbull A, Mincher DJ, Bailly C. Bioconjugate Chem. 2005; 16: 949
- 9c Krantz A, Spencer RW, Tam TF, Liak TJ, Copp LL, Thomas EM, Rafferty SP. J. Med. Chem. 1990; 33: 464
- 10a Maheswari CU, Kumar GS, Venkateshwar M, Kumar RA, Kantam ML, Reddy KR. Adv. Synth. Catal. 2010; 352: 341
- 10b Wang YF, Chen H, Zhu X, Chiba S. J. Am. Chem. Soc. 2012; 134: 11980
- 10c Ma S, Li J, Sun Y, Zhao J, Zhao X, Yang X, Zhang L, Wang L, Zhou Z. Tetrahedron 2006; 62: 7999
- 10d Chu XQ, Xu XP, Meng H, Ji SJ. RSC Adv. 2015; 5: 67829
- 10e Chaitanya M, Anbarasan P. Org. Lett. 2018; 20: 1183
- 10f Cai ZJ, Li FH, Wang SY, Ji SJ. Org. Lett. 2016; 18: 4810
- 10g Huber R, Passera A, Gubler E, Mezzetti A. Adv. Synth. Catal. 2018; 360: 2900
- 10h Wang HX, Wei TQ, Xu P, Wang SY, Ji SJ. J. Org. Chem. 2018; 83: 13491
- 11a Han B, Yang XL, Wang C, Bai YW, Pan TC, Chen X, Yu W. J. Org. Chem. 2012; 77: 1136
- 11b Kobayashi K, Okamura Y, Konishi H. Synthesis 2009; 1494
- 12 Ren ZL, Liu JC, Ding MW. Synthesis 2016; 49: 745
- 13a Wang Y, Tao L, Chen J, He W, Deng H, Shao M, Zhang H, Cao W. Asian J. Org. Chem. 2019; 8: 710
- 13b Giustiniano M, Basso A, Mercalli V, Massarotti A, Novellino E, Tron GC, Zhu J. Chem. Soc. Rev. 2017; 46: 1295
- 13c Dömling A. Chem. Rev. 2006; 106: 17
- 14a Jiang R, Chen J, Huang H, Liu L, Mao L, Liu M, Tian J, Deng F, Zhang X, Wei Y. Dyes Pigm. 2020; 172: 107868
- 14b Youcef SD, Kerim MD, Ilitki H, El Kaïm L. Tetrahedron Lett. 2019; 60: 102
- 14c Krishna PR, Dayaker G, Reddy PV. N. Tetrahedron Lett. 2006; 47: 5977
- 14d van der Eycken E, Peshkov V, Nechaev A, Peshkov A. Synthesis 2016; 48: 2280
- 14e Soeta T, Matsuzaki S, Ukaji Y. J. Org. Chem. 2015; 80: 3688
- 15a Ugi I, Meyr R. Chem. Ber. 1961; 94: 2229
- 15b Neochoritis CG, Zhao T, Dömling A. Chem. Rev. 2019; 119: 1970
- 16a Nixey T, Hulme C. Tetrahedron Lett. 2002; 43: 6833
- 16b Yue T, Wang MX, Wang DX, Zhu J. Angew. Chem. Int. Ed. 2008; 47: 9454
- 16c Yanai H, Sakiyama T, Oguchi T, Taguchi T. Tetrahedron Lett. 2012; 53: 3161
- 16d Chandgude AL, Dömling A. Green Chem. 2016; 18: 3718
- 17a Cowley RE, Golder MR, Eckert NA, Al-Afyouni MH, Holland PL. Organometallics 2013; 32: 5289
- 17b Cowley RE, Eckert NA, Elhaik J, Holland PL. Chem. Commun. 2009; 1760
- 17c Ansari AJ, Pathare RS, Maurya AK, Agnihotri VK, Khan S, Roy TK, Sawant DM, Pardasani RT. Adv. Synth. Catal. 2018; 360: 290
- 18a Wiese S, Aguila MJ. B, Kogut E, Warren TH. Organometallics 2013; 32: 2300
- 18b Pathare RS, Ansari AJ, Verma S, Maurya A, Maurya AK, Agnihotri VK, Sharon A, Pardasani RT, Sawant DM. J. Org. Chem. 2018; 83: 9530
- 18c Zhang Z, Xiao F, Huang B, Hu J, Fu B, Zhang Z. Org. Lett. 2016; 18: 908
- 18d Haldon E, Besora M, Cano I, Cambeiro XC, Pericas MA, Maseras F, Nicasio MC, Perez PJ. Chem. Eur. J. 2014; 20: 3463
- 19 Zhang Z, Li Z, Fu B, Zhang Z. Chem. Commun. 2015; 51: 16312
- 20 Wang F, Xu P, Liu B.-B, Wang SY, Ji SJ. Org. Chem. Front. 2019; 6: 3754
- 21a Xiong J, Min Q, Yao G, Zhang JA, Yu HF, Ding MW. Synlett 2019; 30: 1053
- 21b Xiong J, Wei X, Wan YC, Ding MW. Tetrahedron 2019; 75: 1072
- 21c Xiong J, Wei X, Yan YM, Ding MW. Tetrahedron 2017; 73: 5720
- 22a Nguyen AI, Zarkesh RA, Lacy DC, Thorson MK, Heyduk AF. Chem. Sci. 2011; 2: 166
- 22b Qiao G, Zhang Z, Huang B, Zhu L, Xiao F, Zhang Z. 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.