A Facile Linking of the Pyrrole Ring with Functionalized 3(2H)-Furanone Moieties

Anastasiya G. Malkina; Olesya A. Shemyakina; Anton V. Stepanov; Olga G. Volostnykh; Igor A. Ushakov; Lyubov N. Sobenina; Tatyana N. Borodina; Vladimir I. Smirnov; Boris A. Trofimov

doi:10.1055/s-0035-1560754

Synthesis, Table of Contents

Synthesis 2016; 48(02): 271-280
DOI: 10.1055/s-0035-1560754

paper

A Facile Linking of the Pyrrole Ring with Functionalized 3(2H)-Furanone Moieties

Anastasiya G. Malkina

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Olesya A. Shemyakina

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Anton V. Stepanov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Olga G. Volostnykh

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Igor A. Ushakov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Lyubov N. Sobenina

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Tatyana N. Borodina

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Vladimir I. Smirnov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

,

Boris A. Trofimov*

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

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Abstract

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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 derivatives

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References

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

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