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Synlett 2015; 26(16): 2296-2300
DOI: 10.1055/s-0035-1560091
DOI: 10.1055/s-0035-1560091
letter
Palladium-Catalyzed Tandem Approach to 3-(Diarylmethylene)oxindoles Using Microwave Irradiation
Further Information
Publication History
Received: 14 June 2015
Accepted after revision: 10 July 2015
Publication Date:
12 August 2015 (online)
Abstract
We developed a rapid and efficient microwave-assisted tandem reaction for the synthesis of 3-(diarylmethylene)oxindoles. Three palladium-catalyzed reactions (Sonogashira, Heck, and Suzuki–Miyaura reactions) were combined under microwave irradiation conditions to produce 3-(diarylmethylene)oxindoles from simple propiolamides, aryl iodides, and arylboronic acids. The addition of Ag3PO4 enhanced the yield and stereoselectivity of the tandem reaction significantly.
Key words
microwave irradiation - Sonogashira reaction - Heck reaction - Suzuki–Miyaura reaction - tandem reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560091.
- Supporting Information
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References and Notes
- 1a D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
- 1b Shiri M. Chem. Rev. 2012; 112: 3508
- 1c Rotstein BH, Zaretsky S, Rai V, Yudin AK. Chem. Rev. 2014; 114: 8323
- 1d Kaïm LE, Grimaud L. Eur. J. Org. Chem. 2014; 7749
- 2a Rujiter E, Scheffelaar R, Orru RV. A. Angew. Chem. Int. Ed. 2011; 50: 6234
- 2b Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
- 2c Kotha S, Chavan AS, Goyal D. ACS Comb. Sci. 2015; 17: 253
- 3 Dong GR, Park S, Lee D, Shin KJ, Seo JH. Synlett 2013; 24: 1993
- 4 Yu L.-F, Li Y.-Y, Su M.-B, Zhang M, Zhang W, Zhang L.-N, Pang T, Zhang R.-T, Liu B, Li J.-Y, Li J, Nan F.-J. ACS Med. Chem. Lett. 2013; 4: 475
- 5a Lv K, Wang L.-L, Zhou X.-B, Liu M.-L, Liu H.-Y, Zheng Z.-B, Li S. Med. Chem. Res. 2013; 22: 1723
- 5b Pal A, Ganguly a, Ghosh A, Yousuf M, Rathore B, Banerjee R, Adhikari S. ChemMedChem 2014; 9: 727
- 6 According to unpublished results from our group, Ag3PO4 is a better silver salt additive for the reaction than AgOTf, which was used in previous work (see ref. 3).
- 7a Lidström P, Tierney J, Wathey B, Westman J. Tetrahedron 2001; 57: 9225
- 7b Kappe CO. Angew. Chem. Int. Ed. 2004; 43: 6250
- 7c de la Hoz A, Díaz-Oritz Á, Moreno A. Chem. Soc. Rev. 2005; 34: 164
- 7d Herrero MA, Kremsner JM, Kappe CO. J. Org. Chem. 2008; 73: 36
- 7e Singh BK, Kaval S, Tomar S, Eycken EV, Parmar VS. Org. Process Res. Dev. 2008; 12: 468
- 8a Karabelas K, Westerlud C, Hallberg A. J. Org. Chem. 1985; 50: 3896
- 8b Cabri W, Candiani I, Bedeschi A, Penco S. J. Org. Chem. 1992; 57: 1481
- 8c Ashimori A, Overman LE. J. Org. Chem. 1992; 57: 4751
- 8d Weibei J.-M, Blanc A, Pale P. Chem. Rev. 2008; 108: 3149
- 9a Zou G, Zhu J, Tang J. Tetrahedron Lett. 2003; 44: 8709
- 9b Yang F, Wu Y. Eur. J. Org. Chem. 2007; 3476
- 9c Zhou M.-B, Wei W.-T, Xie Y.-X, Lei Y, Li J.-H. J. Org. Chem. 2010; 75: 5635
- 10 Palladium-Catalyzed Tandem Reaction under Microwave Irradiation; General Procedure: A microwave reaction vial was charged with N-methylpropiolamide (0.5 mmol, 1.0 equiv), aryl iodide (0.55 mmol, 1.1 equiv), aryl boronic acid (0.65 mmol, 1.3 equiv), CuI (0.025 mmol, 5 mol%), NaOAc (1.5 mmol, 3.0 equiv), Pd(PPh3)4 (0.05 mmol, 10 mol%), Ag3PO4 (0.55 mmol, 1.1 equiv), and DMF (5 mL). The reaction vial was sealed and exposed to microwave irradiation conditions for the indicated time and temperature. The mixture was cooled to 25 °C and diluted with EtOAc (200 mL). The organic layer was washed with H2O (3 × 30 mL) and brine (30 mL), then dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel; hexane–EtOAc) to give 3-(diarylmethylene)oxindoles 6 and 9. (Z)-3-[(3-Methoxyphenyl)(phenyl)methylene]-1-methylindolin-2-one [(Z)-9k]: Yellow solid; mp 118.2 °C; Rf = 0.21 (silica gel; hexanes–EtOAc, 4:1). IR (film): 3535, 3055, 2927, 2214, 1700, 1604, 1096, 734 cm–1. 1H NMR (500 MHz, CDCl3): δ = 7.43–7.41 (m, 3 H), 7.33–7.29 (m, 3 H), 7.15 (td, J = 7.7, 1.0 Hz, 1 H), 6.95 (d, J = 7.8 Hz, 1 H), 6.91 (dd, J = 8.3, 1.9 Hz, 1 H), 6.83 (t, J = 1.9 Hz, 1 H), 6.76 (d, J = 7.8 Hz, 1 H), 6.66 (td, J = 7.7, 1.0 Hz, 1 H), 6.42 (d, J = 7.6 Hz, 1 H), 3.76 (s, 3 H), 3.20 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 166.8, 159.3, 154.3, 143.5, 141.5, 141.3, 129.3, 129.3, 129.1, 128.9, 128.9, 124.5, 123.3, 122.5, 121.5, 115.7, 114.4, 107.8, 55.4, 26.0. HRMS (EI): m/z calcd for C23H19NO2: 341.1416; found: 341.1422. (E)-3-[(3-Methoxyphenyl)(phenyl)methylene]-1-methylindolin-2-one [(E)-9k]: Yellow solid; mp 53.0 °C; Rf = 0.26 (silica gel; hexanes–EtOAc, 4:1). IR (film): 3287, 3055, 2937, 1700, 1604, 1469, 1094, 698 cm–1. 1H NMR (500 MHz, CDCl3): δ = 7.37–7.33 (m, 6 H), 7.16 (td, J = 7.7, 1.1 Hz, 1 H), 6.98 (ddd, J = 8.3, 2.6, 0.9 Hz, 1 H), 6.77 (dt, J = 9.9, 1.9 Hz, 1 H), 6.84 (dd, J = 2.5, 1.6 Hz, 1 H), 6.76 (d, J = 7.8 Hz, 1 H), 6.69 (td, J = 7.7, 1.0 Hz, 1 H), 6.48 (d, J = 7.3 Hz, 1 H), 3.77 (s, 3 H), 3.20 (s, 3 H). 13C NMR (125 MHz, CDCl3): δ = 166.9, 160.1, 154.4, 143.5, 142.7, 139.9, 130.2, 130.0, 129.2, 128.9, 128.0, 124.4, 123.5, 123.3, 121.7, 121.6, 115.0, 114.5, 107.8, 55.5, 26.0. HRMS (EI): m/z [M+] calcd for C23H19NO2: 341.1416; found 341.1417.
For selective reviews of multicomponent tandem reaction, see:
For selective reviews of diversity-oriented synthesis (DOS) related to multicomponent reactions, see:
For selective reviews of microwave-assisted reaction, see:
For examples of silver-mediated Sonogashira reaction, see: