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Synthesis 2014; 46(24): 3309-3314
DOI: 10.1055/s-0034-1379030
DOI: 10.1055/s-0034-1379030
paper
Bromotriphenylphosphonium Salt Promoted One-Pot Cyclization to 2-Fluoroalkyl-Substituted Indoles
Weitere Informationen
Publikationsverlauf
Received: 19. Juni 2014
Accepted after revision: 05. August 2014
Publikationsdatum:
08. September 2014 (online)
Abstract
2-Fluoroalkyl-substituted indoles were prepared in moderate to excellent yields through bromotriphenylphosphonium salt promoted ring formation with fluorine-containing carboxylic acids in the presence of triethylamine in toluene at reflux temperature. A range of 2-fluoroalkyl-substituted indole derivatives can be conveniently prepared.
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References
- 2a Van Zandt MC, Jones ML, Gunn DE, Geraci LS, Jones JH, Sawicki DR, Sredy J, Jacot JL, Dicioccio AT, Petrova T, Mitschler A, Podjarny AD. J. Med. Chem. 2005; 48: 3141
- 2b Granchi C, Roy S, Giacomelli C, Macchia M, Tuccinardi T, Martinelli A, Lanza M, Betti L, Giannaccini G, Lucacchini A, Funel N, Leon LG, Giovannetti E, Peters GJ, Palchaudhuri R, Calvaresi EC, Hergenrother PJ, Minutolo F. J. Med. Chem. 2011; 54: 1599
- 2c Granchi C, Roy S, Mottinelli M, Nardini E, Campinoti F, Tuccinardi T, Lanza M, Betti L, Giannaccini G, Lucacchini A, Martinelli A, Macchia M, Minutolo F. Bioorg. Med. Chem. Lett. 2011; 21: 7331
- 3a Humphrey GR, Kuethe JT. Chem. Rev. 2006; 106: 2875
- 3b Muzalevskiy VM, Shastin AV, Balenkova ES, Haufe G, Nenajdenko VG. Synthesis 2009; 3905
- 3c Cacchi S, Fabrizi G. Chem. Rev. 2011; 111: 215
- 3d Gonzalo B, Isabel F, Pedro JR, Carlos V. Synthesis 2012; 44: 3590
- 4a Kraxner J, Hübner H, Gmeiner P. Arch. Pharm. Pharm. Med. Chem. 2000; 333: 287
- 4b Pichota A, Gramlich V, Beck AK, Seebach D. Helv. Chim. Acta 2012; 95: 1239
- 4c Liao S, Alfaro-Lopez J, Shenderovich MD, Hosohata K, Lin J, Li X, Stropova D, Davis P, Jernigan KA, Porreca F, Yamamura HI, Hruby VJ. J. Med. Chem. 1998; 41: 4767
- 4d Romanov-Michailidis F, Guénée L, Alexakis A. Org. Lett. 2013; 15: 5890
- 5a Rabinowitz R, Marcus R. J. Am. Chem. Soc. 1962; 84: 1312
- 5b Ramirez F, Desai NB, Mckelvie N. J. Am. Chem. Soc. 1962; 84: 1745
- 5c Gadogan JI. G, Mackie RK. Chem. Soc. Rev. 1974; 3: 87
- 6 Wang Z, Ge F, Wan W, Jiang H, Hao J. J. Fluorine Chem. 2007; 128: 1143
-
7 Tamura K, Mizukami H, Maeda K, Watanabe H, Uneyama K. J. Org. Chem. 1993; 58: 32
- 8 Ge F, Wang Z, Wan W, Lu W, Hao J. Tetrahedron Lett. 2007; 48: 3251
- 9 Wang Z, Wan W, Jiang H, Hao J. J. Org. Chem. 2007; 72: 9364
- 10 Evans DA, Peterson GS, Johnson JS, Barnes DM, Campos KR, Woerpel KA. J. Org. Chem. 1998; 63: 4541
- 11 Yoshida M, Yoshida T, Kobayashi M, Kamigata N. J. Chem. Soc., Perkin Trans. 1 1989; 909
- 12 Miyashita K, Tsuchiya K, Kondoh K, Miyabe H, Imanishi T. J. Chem. Soc., Perkin Trans. 1 1996; 1261
- 13 Bujok R, Wróbel Z, Wojciechowski K. Synlett 2012; 23: 1315
For leading references on the biological activities of indoles, see:
For recent reviews on the synthesis of indoles, see: