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Synthesis 2016; 48(19): 3364-3372
DOI: 10.1055/s-0035-1562513
DOI: 10.1055/s-0035-1562513
paper
Synthesis of 3-Substituted Chromones and Quinolones from Enaminones
Further Information
Publication History
Received: 13 May 2016
Accepted after revision: 16 June 2016
Publication Date:
26 July 2016 (online)
Dedicated to Prof. Normant in honor of his scientific achievements within his career
Abstract
A facile and efficient synthetic route to 3-substituted chromones and quinolones was developed. Silver triflate was employed to activate the electrophile to react with various readily available enaminones.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562513.
- Supporting Information
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References
- 1 Bisacchi GS. J. Med. Chem. 2015; 58: 4874
- 2 Singh S, Kaur G, Mangla V, Gupta MK. J. Enzyme Inhib. Med. Chem. 2015; 30: 492
- 3 Bisacchi G, Hale M. Curr. Med. Chem. 2016; 23: 520
- 4 Wube A, Hüfner A, Seebacher W, Kaiser M, Brun R, Bauer R, Bucar F. Molecules 2014; 19: 14204
- 5 Nilsen A, Miley GP, Forquer IP, Mather MW, Katneni K, Li Y, Pou S, Pershing AM, Stickles AM, Ryan E, Kelly JX, Doggett JS, White KL, Hinrichs DJ, Winter RW, Charman SA, Zakharov LN, Bathurst I, Burrows JN, Vaidya AB, Riscoe MK. J. Med. Chem. 2014; 57: 3818
- 6 Cross RM, Monastyrskyi A, Mutka TS, Burrows JN, Kyle DE, Manetsch R. J. Med. Chem. 2010; 53: 7076
- 7 Zhang Y, Clark JA, Connelly MC, Zhu F, Min J, Guiguemde WA, Pradhan A, Iyer L, Furimsky A, Gow J, Parman T, El Mazouni F, Phillips MA, Kyle DE, Mirsalis J, Guy RK. J. Med. Chem. 2012; 55: 4205
- 8 Gaspar A, Matos MJ, Garrido J, Uriarte E, Borges F. Chem. Rev. 2014; 114: 4960
- 9 Keri RS, Budagumpi S, Pai RK, Balakrishna RG. Eur. J. Med. Chem. 2014; 78: 340
- 10 El-Borai MA, Rizk HF, Beltagy DM, El-Deeb IY. Eur. J. Med. Chem. 2013; 66: 415
- 11 Salomone A, Perna FM, Sassone FC, Falcicchio A, Bezenšek J, Svete J, Stanovnik B, Florio S, Capriati V. J. Org. Chem. 2013; 78: 11059
- 12 Xiang D, Xin X, Liu X, Zhang R, Yang J, Dong D. Org. Lett. 2012; 14: 644
- 13 Liermann JC, Elnagdi MH, Meier H. Magn. Reson. Chem. 2013; 51: 16
- 14 Wan J.-P, Pan Y.-J. Chem. Commun. 2009; 2768
- 15 Gammill RB. Synthesis 1979; 901
- 16 Yokoe I, Maruyama K, Sugita Y, Harashida T, Shirataki Y. Chem. Pharm. Bull (Tokyo) 1994; 42: 1697
- 17 Appel B, Rotzoll S, Kranich R, Reinke H, Langer P. Eur. J. Org. Chem. 2006; 3638
- 18 Bornadiego A, Díaz J, Marcos CF. Adv. Synth. Catal. 2014; 356: 718
- 19 Mkrtchyan S, Iaroshenko VO, Dudkin S, Gevorgyan A, Vilches-Herrera M, Ghazaryan G, Volochnyuk DM, Ostrovskyi D, Ahmed Z, Villinger A, Sosnovskikh VY, Langer P. Org. Biomol. Chem. 2010; 8: 5280
- 20 Löwe W, Matzanke N, Rütjes T. Arch. Pharm. (Weinheim) 1994; 327: 819
- 21 Löwe W, Kennemann A. Arch. Pharm. (Weinheim) 1985; 318: 239
- 22 Xiang H, Yang C. Org. Lett. 2014; 16: 5686
- 23 Engelhart CA, Aldrich CC. J. Org. Chem. 2013; 78: 7470
- 24 Löwe W, Schmidt R. J. Heterocycl. Chem. 1995; 32: 271
- 25 Löwe W, Rütjes T. J. Heterocycl. Chem. 1995; 32: 43
- 26 Panja SK, Maiti S, Bandyopadhyay C. J. Chem. Res. 2010; 34: 555
- 27 Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
- 28 Mutai P, Pavadai E, Wiid I, Ngwane A, Baker B, Chibale K. Bioorg. Med. Chem. Lett. 2015; 25: 2510
- 29 Broutin P.-E, Hilty P, Thomas AW. Tetrahedron Lett. 2003; 44: 6429