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Synthesis 2016; 48(02): 271-280
DOI: 10.1055/s-0035-1560754
DOI: 10.1055/s-0035-1560754
paper
A Facile Linking of the Pyrrole Ring with Functionalized 3(2H)-Furanone Moieties
Further Information
Publication History
Received: 02 August 2015
Accepted after revision: 24 September 2015
Publication Date:
29 October 2015 (online)
Abstract
The CN-functionalized pyrrole(indole)-3(2H)-furanone derivatives are readily synthesized via the domino reaction of diverse pyrrole(indole) carboxylic acids with tertiary cyanopropargylic alcohols (Et3N, MeCN, MW reactor, 100 °C, 1.2 atm) in up to 93% yield.
Key words
pyrrole(indole)-2-carboxylic acids - tertiary cyanopropargylic alcohols - domino reaction - cyclization - pyrrole(indole)-3(2H)-furanone derivativesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560754.
- Supporting Information
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References
- 1a Taylor EC, Jones RA. Pyrroles . Wiley; New York: 1990
- 1b Sundburg RJ In Comprehensive Heterocyclic Chemistry II . Vol. 2. Katritzky AR, Rees CW, Scriven EF. V. Pergamon Press; Oxford: 1996: 119
- 1c Fan H, Peng J, Hamann MT, Hu J.-F. Chem. Rev. 2008; 108: 264
- 2a Miyaji H, Sato W, Sessler JL. Angew. Chem. Int. Ed. 2000; 39: 1777
- 2b Yoon D.-W, Hwang H, Lee C.-H. Angew. Chem. Int. Ed. 2002; 41: 1757
- 2c Gabriel S, Cécius M, Fleury-Frenette K, Cossement D, Hecq M, Ruth N, Jérôme R, Jérôme C. Chem. Mater. 2007; 19: 2364
- 2d Ramanavicius A, Ramanaviciene A, Malinauskas A. Electrochem. Acta 2006; 51: 6025
- 2e Pu S, Liu G, Shen L, Xu J. Org. Lett. 2007; 9: 2139
- 3a Gałęzowski M, Gryko DT. Curr. Org. Chem. 2007; 11: 1310
- 3b Trofimov BA, Nedolya NA In Comprehensive Heterocyclic Chemistry III . Vol. 3. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008: 45
- 3c Trofimov BA, Mikhaleva AI, Schmidt EY, Sobenina LN. Chemistry of Pyrroles. CRC Press; Boca-Raton: 2014
- 4a Zeng L, Miller EW, Pralle A, Isacoff EY, Chang CJ. J. Am. Chem. Soc. 2006; 128: 10
- 4b La Regina G, Silvestri R, Artico M, Lavecchia A, Novellino E, Befani O, Turini P, Agostinelli E. J. Med. Chem. 2007; 50: 922
-
4c Estévez V, Villacampa M, Menéndez JC. Chem. Soc. Rev. 2010; 39: 4402
- 5a Tao H, Hwang I, Boger DL. Bioorg. Med. Chem. Lett. 2004; 14: 5979
- 5b Wakabayashi K, Miyachi H, Hashimoto Y, Tanatani A. Bioorg. Med. Chem. Lett. 2005; 13: 2837
- 5c Rochais C, Lisowski V, Dallemagne P, Rault S. Bioorg. Med. Chem. 2006; 14: 8162
- 5d Clark BR, Capon RJ, Lacey E, Tennant S, Gill JH. Org. Lett. 2006; 8: 701
- 6a Di Santo R, Costi R, Artico M, Miele G, Lavecchia A, Novellino E, Bergamini A, Cancio R, Maga G. ChemMedChem 2006; 1: 1367
- 6b Teixeira C, Barbault F, Rebehmed J, Liu K, Xie L, Lu H, Jiang S, Fan B, Maurel F. Bioorg. Med. Chem. 2008; 16: 3039
- 6c He XY, Zou P, Qiu J, Hou L, Jiang S, Liu S, Xie L. Bioorg. Med. Chem. Lett. 2011; 12: 6726
- 6d Wang C, Shi W, Cai L, Lu L, Wang Q, Zhang T, Li J, Zhang Z, Wang K, Xu L, Jiang X, Jiang S, Liu K. J. Med. Chem. 2013; 56: 2527
- 6e Regueiro-Ren A, Xue QM, Swidorski JJ, Gong Y.-F, Mathew M, Parker DD, Yang Z, Eggers B, D’Arienzo C, Sun Y, Malinowski J, Gao Q, Wu D, Langley DR, Colonno RJ, Chien CM, Grasela D, Zheng M, Lin P.-F, Meanwell NA, Kadow JF. J. Med. Chem. 2013; 56: 1656
- 6f Di Santo R. J. Med. Chem. 2014; 57: 539
- 7a Deidda D, Lampis G, Fioravanti R, Biava M, Porretta GC, Zanetti S, Pompei R. Antimicrob. Agents Chemother. 1998; 42: 3035
- 7b Ragno R, Marshall GR, Di Santo R, Costi R, Massa S, Rompei R, Artico M. Bioorg. Med. Chem. 2000; 8: 1423
- 7c Biava M, Porretta GC, Deidda D, Pompei R, Tafic A, Manettic F. Bioorg. Med. Chem. 2004; 12: 1453
- 7d Protopopova M, Bogatcheva E, Nikonenko B, Hundert S, Einck L, Nacy CA. Med. Chem. 2007; 3: 301
- 7e Janin YL. Bioorg. Med. Chem. 2007; 15: 2479
- 7f Biava M, Porretta GC, Poce G, De Logu A, Saddi M, Meleddu R, Manetti F, De Rossi E, Botta M. J. Med. Chem. 2008; 51: 3644
- 8 Joshi SD, More UA, Kulkarni VH, Aminabhavi TM. Curr. Org. Chem. 2013; 17: 2279
- 9a Parker W, Raphael RA, Wilkinson DI. J. Chem. Soc. 1958; 3871
- 9b Jackson RF. W, Raphael RA. Tetrahedron Lett. 1983; 24: 2117
- 9c Felman SW, Jirkovsky I, Memoli KA, Borella L, Wells C, Russell J, Ward J. J. Med. Chem. 1992; 35: 1183
- 9d Villemin D, Jaffrès P.-A, Hachémi M. Tetrahedron Lett. 1997; 38: 537
-
9e Reiter M, Turner H, Mills-Webb R, Gouverneur V. J. Org. Chem. 2005; 70: 8478
- 9f Haung TT, Kirsch SF In Targets in Heterocyclic Systems: Chemistry and Properties . Vol. 13. Attanasi OA, Spinelli D. Societa Chimica Italiana; Rome: 2009: 57 ; and references cited therein
- 9g Poonoth M, Krause N. J. Org. Chem. 2011; 76: 1934
- 10a Jerris PJ, Smith III AB. J. Org. Chem. 1981; 46: 577
- 10b Sakai T, Ito H, Yamawaki A, Takeda A. Tetrahedron Lett. 1984; 25: 2987
- 10c Manfredini S, Baraldi PG, Bazzanini R, Guarneri M, Simoni D, Balzarini J, De Clercq E. J. Med. Chem. 1994; 37: 2401
- 10d Chimichi S, Boccalini M, Cosimelli B, Viola G, Vedaldi D, Dall’Acqua F. Tetrahedron Lett. 2002; 43: 7473
- 10e Viola G, Vedaldi D, Dall’Acqua F, Basso G, Disarò S, Spinelli M, Cosimelli B, Boccalini M, Chimichi S. Chem. Biodiv. 2004; 1: 1265
- 10f Chimichi S, Boccalini M, Cravotto G, Rosati O. Tetrahedron Lett. 2006; 47: 2405
- 10g Crone B, Kirsch SF. J. Org. Chem. 2007; 72: 5435
- 10h Chimichi S, Boccalini M, Salvador A, Dall’Acqua F, Basso G, Viola G. ChemMedChem 2009; 4: 769
- 10i Egi M, Azechi K, Saneto M, Shimizu K, Akai S. J. Org. Chem. 2010; 75: 2123
- 11a Raffauf RF, Huang P.-KC, Le Quesne PW, Levery SB, Brennan TF. J. Am. Chem. Soc. 1975; 97: 6884
- 11b Le Quesne PW, Levery SB, Menachery MD, Brennan TF, Raffauf RF. J. Chem. Soc., Perkin Trans. 1 1978; 1572
- 11c Takao K, Ochiai H, Hashizuka T, Koshimura H, Tadano K, Ogawa S. Tetrahedron Lett. 1995; 36: 1487
- 11d Takao K, Ochiai H, Yoshida K, Hashizuka T, Koshimura H, Tadano K, Ogawa S. J. Org. Chem. 1995; 60: 8179
- 11e Li Y, Hale KJ. Org. Lett. 2007; 9: 1267
- 12a Kupchan SM, Sigel CW, Matz MJ, Gilmore CJ, Bryan RF. J. Am. Chem. Soc. 1976; 98: 2295
-
12b Smith III AB, Guaciaro MA, Schow SR, Wovkulich PM, Toder BH, Hall TW. J. Am. Chem. Soc. 1981; 103: 219
- 12c Smith III AB, Malamas MS. J. Org. Chem. 1982; 47: 3442
- 12d Taylor MD, Smith III AB, Furst GT, Gunasekara SP, Bevelle CA, Cordell GA, Farmworth NR, Kupchan SM, Uchida H, Branfman AR, Dailey RG. Jr, Sneden AT. J. Am. Chem. Soc. 1983; 105: 3177
- 12e Schmeda-Hirschmann G, Razmilic I, Sauvain M, Moretti C, Muñoz V, Ruiz E, Balanza E, Fournet A. Phytother. Res. 1996; 10: 375
- 12f Pertino M, Schmeda-Hirschmann G, Santos LS, Rodríguez JA, Theoduloz C. Z. Naturforsch. 2007; 62b: 275
- 13a Shao X, Tamm C. Tetrahedron Lett. 1991; 32: 2891
- 13b Ishikawa M, Ninomiya T. J. Antibiot. 2008; 61: 692
- 13c Ishikawa M, Ninomiya T, Akabane H, Kushida N, Tsujiuchi G, Ohyama M, Gomi S, Shito K, Murata T. Bioorg. Med. Chem. Lett. 2009; 19: 1457
- 14 Li Z, Nakashige M, Chain WJ. J. Am. Chem. Soc. 2011; 133: 6553
- 15a Chimichi S, Boccalini M, Cosimelli B, Dall’Acqua F, Viola G. Tetrahedron 2003; 59: 5215
- 15b Rappai JP, Raman V, Unnikrishnan PA, Prathapan S, Thomas SK, Paulose CS. Bioorg. Med. Chem. Lett. 2009; 19: 764
- 16 Mack RA, Zazulak WI, Radov LA, Baer JE, Stewart JD, Elzer PH, Kinsolving CR, Georgiev VS. J. Med. Chem. 1988; 31: 1910
- 17a Sasaki T, Yamakoshi J, Saito M, Kasai K, Matsudo T, Koga T, Mori K. Biosci. Biotechnol. Biochem. 1998; 62: 1865
- 17b Sasaki T, Yamakoshi J, Saito M, Kasai K, Matsudo T, Kikuchi M, Koga T, Mori K. Biosci. Biotechnol. Biochem. 1998; 62: 2145
- 18a Silverstein FE, Faich G, Goldstein JL, Simon LS, Pincus T, Whelton A, Makuch R, Eisen G, Agrawal NM, Stenson WF, Burr AM, Zhao WW, Kent JD, Lefkowith JB, Verburg KM, Geis GS. J. Am. Med. Assoc. 2000; 284: 1247
- 18b Shin SS, Byun Y, Lim KM, Choi JK, Lee K.-W, Moh JH, Kim JK, Jeong YS, Kim JY, Choi YH, Koh H.-J, Park Y.-H, Oh YI, Noh M.-S, Chung S. J. Med. Chem. 2004; 47: 792
- 18c Shamshina JL, Snowden TS. Tetrahedron Lett. 2007; 48: 3767
- 19 Jung J.-K, Semple G, Johnson BR. US Patent 7803837 B2, 2010
- 20 Okombi S, Rival D, Bonnet S, Mariotte A.-M, Perrier E, Boumendjel A. J. Med. Chem. 2006; 49: 329
- 21 Ghosh S, Khamarui S, Gayen KS, Maiti DK. Sci. Rep. 2013; 3: 2987
- 22 Trofimov BA, Shemyakina OA, Mal’kina AG, Ushakov IA, Kazheva ON, Alexandrov GG, Dyachenko OA. Org. Lett. 2010; 12: 3200
- 23 Sobenina LN, Sergeeva MP, Mikhaleva AI, Sigalov MV, Korostova SE, Golovanova NI, Salaurov VN, Bakhareva EV, Vasil’eva NN. Khim. Geterocicl. Soed. 1990; 612 ; Chem. Abstr. 1991, 114, 23739
- 24a Landor SR, Demetriou B, Grzeskowiak R, Pavey D. J. Organomet. Chem. 1975; 93: 129
- 24b Trofimov BA, Mal’kina AG, Skvortsov YuM. Zh. Org. Khim. 1993; 29: 1268 ; Chem. Abstr. 1994, 120, 216196
- 24c Hopf H, Witulski B. Functionalized Acetylenes in Organic Synthesis - The Case of the 1-Cyano- and 1-Halogenoacetylenes, In Modern Acetylene Chemistry. Stang PJ, Diederich F. VCH; Weinheim: 1995: 33
- 24d Trofimov BA, Mal’kina AG. Heterocycles 1999; 51: 2485
- 24e Trofimov BA, Andriyankova LV, Shaikhudinova SI, Kazantseva TI, Mal’kina AG, Afonin AV. Synthesis 2002; 853
- 25 Sorgi KL. Encyclopedia of Reagents for Organic Synthesis. Wiley; New York: 2001
- 26 Katritzky AR. Handbook of Heterocyclic Chemistry . Elsevier; Amsterdam: 2013
- 27a Miller SI, Tanaka R. Selective Organic Transformation . Vol. 1. Thyagarajan BS. Wiley-Interscience; New York: 1970: 143
- 27b Dickstein JI, Miller SI. In The Chemistry of the Carbon-Carbon Triple Bond . Part 2; Patai S. Wiley; New York: 1978: 881
- 28 Sheldrick GM. Acta Crystallogr., Sect. D 2008; 64: 112