Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydro­furans

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

doi:10.1055/s-0035-1561591

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(12): 1880-1891
DOI: 10.1055/s-0035-1561591

special topic

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans

Anastasiya G. Malkina

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

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

It is shown for the first time that the reaction of cyanopropargylic alcohols with carboxylic acids in the presence of triethylamine (5–100 mol%) under microwave irradiation (MeCN, 100 °C, 1.2 atm) follows two competing pathways to afford 4-cyano-3(2H)-furanones (1:1 adduct) and 4-cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans (2:1 adduct) in moderate to good yields. The ratio of the products depends on both the reaction conditions (the reactant ratio, catalyst content) and the reactant structure, the 2:1 adduct formation being favored by an excess of cyanopropargylic alcohol, lower catalyst content, and bulky substituents at the carboxylic functions. Both competing reactions proceed via the same intermediates, keto esters, which either intramolecularly cyclize to the 1:1 adducts, or intermolecularly add the second molecule of cyanopropargylic alcohol to give the 2:1 adducts.

Key words

cyanopropargylic alcohols - carboxylic acids - nucleophilic addition - cyclization - 3(2H)-furanones - 2,3-dihydrofuran derivatives

Volltext

Referenzen

References

1a Alvarez-Builla J, Vaquero JJ, Barluenga J. Modern Heterocyclic Chemistry. Vol. 1. Wiley-VCH; Weinheim: 2011
1b Eftekhari-Sis B, Zirak M. Chem. Rev. 2015; 115: 151

2a 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
2b Amslinger S, Lindner SK. Synthesis 2011; 2671
2c John J, Târcoveanu E, Jones PG, Hopf H. Beilstein J. Org. Chem. 2014; 1462

3 Kilroy TG, O’Sullivan TP, Guiry PJ. Eur. J. Org. Chem. 2005; 4929 ; and references cited therein

4a Jerris PJ, Smith III AB. J. Org. Chem. 1981; 46: 577
4b Manfredini S, Baraldi PG, Bazzanini R, Guarneri M, Simoni D, Balzarini J, De Clercq E. J. Med. Chem. 1994; 37: 2401
4c Chimichi S, Boccalini M, Cosimelli B, Viola G, Vedaldi D, Dall’Acqua F. Tetrahedron Lett. 2002; 43: 7473
4d Viola G, Vedaldi D, Dall’Acqua F, Basso G, Disarò S, Spinelli M, Cosimelli B, Boccalini M, Chimichi S. Chem. Biodiversity 2004; 1: 1265
4e Chimichi S, Boccalini M, Cravotto G, Rosati O. Tetrahedron Lett. 2006; 47: 2405
4f Crone B, Kirsch SF. J. Org. Chem. 2007; 72: 5435
4g Chimichi S, Boccalini M, Salvador A, Dall’Acqua F, Basso G, Viola G. ChemMedChem 2009; 4: 769
4h Egi M, Azechi K, Saneto M, Shimizu K, Akai S. J. Org. Chem. 2010; 75: 2123

5a Raffauf RF, Huang P.-KC, Le Quesne PW, Levery SB, Brennan TF. J. Am. Chem. Soc. 1975; 97: 6884
5b Le Quesne PW, Levery SB, Menachery MD, Brennan TF, Raffauf RF. J. Chem. Soc., Perkin Trans. 1 1978; 1572
5c Takao K, Ochiai H, Hashizuka T, Koshimura H, Tadano K, Ogawa S. Tetrahedron Lett. 1995; 36: 1487
5d Takao K, Ochiai H, Yoshida K, Hashizuka T, Koshimura H, Tadano K, Ogawa S. J. Org. Chem. 1995; 60: 8179
5e Li Y, Hale KJ. Org. Lett. 2007; 9: 1267

6a Kupchan SM, Sigel CW, Matz MJ, Gilmore CJ, Bryan RF. J. Am. Chem. Soc. 1976; 98: 2295
6b Smith III AB, Guaciaro MA, Schow SR, Wovkulich PM, Toder BH, Hall TW. J. Am. Chem. Soc. 1981; 103: 219
6c Smith III AB, Malamas MS. J. Org. Chem. 1982; 47: 3442
6d 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
6e Schmeda-Hirschmann G, Razmilic I, Sauvain M, Moretti C, Muñoz V, Ruiz E, Balanza E, Fournet A. Phytother. Res. 1996; 10: 375
6f Pertino M, Schmeda-Hirschmann G, Santos LS, Rodríguez JA, Theoduloz C. Z. Naturforsch. B. 2007; 62, 275

7a Nicolaou KC, Kang Q, Ng SY, Chen DY.-K. J. Am. Chem. Soc. 2010; 132: 8219
7b Li Z, Nakashige M, Chain WJ. J. Am. Chem. Soc. 2011; 133: 6553
7c Zhang J, Zheng S, Peng W, Shen Z. Tetrahedron Lett. 2014; 55: 1339
7d Akbulut Y, Gaunt HJ, Muraki K, Ludlow MJ, Amer MS, Bruns A, Vasudev NS, Radtke L, Willot M, Hahn S, Seitz T, Ziegler S, Christmann M, Beech DJ, Waldmann H. Angew. Chem. Int. Ed. 2015; 54: 3787

8a Shao X, Tamm C. Tetrahedron Lett. 1991; 32: 2891
8b Ishikawa M, Ninomiya T. J. Antibiot. 2008; 61: 692
8c Maiya S, Grundmann A, Li X, Li SM, Turner G. ChemBioChem 2007; 8: 1736
8d 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

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 Poonoth M, Krause N. J. Org. Chem. 2011; 76: 1934

10a 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
10b 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
10c Shamshina JL, Snowden TS. Tetrahedron Lett. 2007; 48: 3767

11 Mack RA, Zazulak WI, Radov LA, Baer JE, Stewart JD, Elzer PH, Kinsolving CR, Georgiev VS. J. Med. Chem. 1988; 31: 1910
12 Okombi S, Rival D, Bonnet S, Mariotte A.-M, Perrier E, Boumendjel A. J. Med. Chem. 2006; 49: 329
13 Jung J.-K, Semple G, Johnson BR. U.S. Patent 7803837 B2, 2010
14 Marks KM, Park ES, Arefolov A, Russo K, Ishihara K, Ring JE, Clardy J, Clarke AS, Pelish HE. J. Nat. Prod. 2011; 74: 567
15 Lallemand J.-Y, Six Y, Ricard L. Eur. J. Org. Chem. 2002; 503
16 Huang A.-C, Chung J.-G, Kuo S.-C, Lu H.-F, Lin T.-P. In Vivo 2007; 21: 227

17a Findik E, Dingil A, Karaman I, Budak Y, Ceylan ME. J. Chem. 2009; 6: S53
17b Logoglu E, Yilmaz M, Katircioglu H, Yakut M, Mercan S. Med. Chem. Res. 2010; 19: 490

18a Garzino F, Méou A, Brun P. Synthesis 2003; 598
18b Lee YR, Kang KY, Lee GJ, Lee WK. Synthesis 2003; 1977
18c Garzino F, Méou A, Brun P. Eur. J. Org. Chem. 2003; 1410

19a Chuang C.-P, Tsai A.-I. Synthesis 2006; 675
19b Qian J, Cao W, Zhang H, Chen J, Zhu S. J. Fluorine Chem. 2007; 128: 207
19c Rueping M, Parra A, Uria U, Besselièvre F, Merino E. Org. Lett. 2010; 5680
19d Yilmaz M. Tetrahedron 2011; 67: 8255
19e Yilmaz M, Yilmaz EV. B, Pekel AT. Helv. Chim. Acta 2011; 94: 2027
19f Harikrishnan PS, Rajesh SM, Almansour AI, Perumal S. Arkivoc 2013; (iv): 1
19g Yilmaz M, Biçer E, Ustalar A, Pekel AT. Arkivoc 2014; (v): 225
19h Chagarovsky AO, Budynina EM, Ivanova OA, Villemson EV, Rybakov VB, Trushkov IV, Melnikov MY. Org. Lett. 2014; 16: 2830

20a Yang Z, Fan M, Liu W, Liang Y. Synthesis 2005; 2188
20b Son S, Fu GC. J. Am. Chem. Soc. 2007; 129: 1046
20c Liu C.-R, Zhu B.-H, Zheng J.-C, Sun X.-L, Xie Z, Tang Y. Chem. Commun. 2011; 47: 1342
20d Bouhlel A, Curti C, Tabelé C, Vanelle P. Molecules 2013; 18: 4293
20e Yilmaz M, Burgaz EV, Yakut M, Biçer E. J. Chin. Chem. Soc. 2014; 61: 1101

21a Landor SR, Demetriou B, Grzeskowiak R, Pavey D. J. Organomet. Chem. 1975; 93: 129
21b Trofimov BA, Mal’kina AG, Skvortsov YuM. Zh. Org. Khim. 1993; 29: 1268 ; Chem. Abstr. 1994, 120, 216196
21c 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
21d Trofimov BA, Mal’kina AG. Heterocycles 1999; 51: 2485
21e Trofimov BA, Andriyankova LV, Shaikhudinova SI, Kazantseva TI, Mal’kina AG, Afonin AV. Synthesis 2002; 853
21f Rong G, Mao J, Zheng Y, Yao R, Xu X. Chem. Commun. 2015; 51: 13822

22a Trofimov BA, Shemyakina OA, Mal’kina AG, Ushakov IA, Kazheva ON, Alexandrov GG, Dyachenko OA. Org. Lett. 2010; 12: 3200
22b Shemyakina OA, Mal’kina AG, Nosyreva VV, Ushakov IA, Trofimov BA. Arkivoc 2012; 319
22c Shemyakina OA, Stepanov AV, Volostnykh OG, Mal’kina AG, Ushakov IA, Trofimov BA. Russ. J. Org. Chem. 2014; 50: 1617

23 Mal’kina AG, Volostnykh OG, Petrushenko KB, Shemyakina OA, Nosyreva VV, Ushakov IA, Trofimov BA. Tetrahedron 2013; 69: 3714
24 Trofimov BA, Stepanov AV, Mal’kina AG, Volostnykh OG, Shemyakina OA, Ushakov IA. Synth. Commun. 2015; 45: 2718
25 Mal’kina AG, Volostnykh OG, Stepanov AV, Ushakov IA, Petrushenko KB, Trofimov BA. Synthesis 2013; 45: 3435
26 Malkina AG, Shemyakina OA, Stepanov AV, Volostnykh OG, Ushakov IA, Sobenina LN, Borodina TN, Smirnov VI, Trofimov BA. Synthesis 2016; 48: 271
27 Trofimov BA, Mal’kina AG, Shemyakina OA, Nosyreva VV, Borisova AP, Albanov AI, Kazheva ON, Alexandrov GG, Chekhlov AN, Dyachenko OA. Tetrahedron 2009; 65: 2472
28 CCDC 1411948 (3c) and 1411949 (4c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
29 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
30 Sheldrick GM. Acta Crystallogr., Sect. D 2008; 64: 112

Zusatzmaterial

Supporting Information

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydro­furans

Organocatalyzed Microwave-Assisted Competing Cyclization of Cyanopropargylic Alcohols with Carboxylic Acids: 4-Cyano-3(2H)-furanones versus 4-Cyano-[(Z)-3-cyanomethylene]-2,3-dihydrofurans