Synthesis of Functionalized 5-Amino-3(2H)-furanones via Base-Catalyzed Ring-Cleavage/Recyclization of 4-Cyano-3(2H)-furanones in the Presence of Water

Olga G. Volostnykh; Olesya A. Shemyakina; Anton V. Stepanov; Igor A. Ushakov; Tatyana N. Borodina

doi:10.1055/s-0037-1609916

Synthesis, Table of Contents

Synthesis 2018; 50(24): 4905-4914
DOI: 10.1055/s-0037-1609916

paper

Synthesis of Functionalized 5-Amino-3(2H)-furanones via Base-Catalyzed Ring-Cleavage/Recyclization of 4-Cyano-3(2H)-furanones in the Presence of Water

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: shemyakina@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: shemyakina@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: shemyakina@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: shemyakina@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: shemyakina@irioch.irk.ru

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Abstract

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Abstract

5-Alkyl/aryl/hetaryl-4-cyano-3(2H)-furanones undergo ring-cleavage/recyclization in the presence of water under mild conditions [MOH (M = Na, K), aqueous ethanol, 20–25 °C] to afford 4-acyl/aroyl/hetaroyl-5-amino-3(2Н)-furanones in 75–99% yields.

Key words

3(2H)-furanones - ring-cleavage - recyclization - hydration

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References

References

1a Slaughter JC. Biol. Rev. 1999; 74: 259
1b Haung TT. Kirsch SF. In Targets in Heterocyclic Systems-Chemistry and Properties . Vol. 13. Attanasi OA. Spinelli D. Societa Chimica Italiana; Rome: 2009: 57

2a Farine J.-P. Le Qvere J.-L. Duffy J. Semon E. Brossut R. Biosci. Biotechnol. Biochem. 1993; 57: 2026
2b Choi S.-C. Zhang C. Moon S. Oh Y.-S. J. Microbiol. 2014; 52: 734
2c Schauder S. Bassler BL. Genes Dev. 2001; 15: 1468

3a Parker W. Raphael RA. Wilkinson DI. J. Chem. Soc. 1958; 3871
3b Jackson RF. W. Raphael R. Tetrahedron Lett. 1983; 24: 2117
3c Felman SW. Jirkovsky I. Memoli KA. Borella L. Wells C. Russell J. Ward J. J. Med. Chem. 1992; 35: 1183
3d Villemin D. Jaffrès P.-A. Hachémi M. Tetrahedron Lett. 1997; 38: 537
3e Reiter M. Turner H. Mills-Webb R. Gouverneur V. J. Org. Chem. 2005; 70: 8478

4a Jerris PJ. Smith AB. III. J. Org. Chem. 1981; 46: 577
4b Sakai T. Ito H. Yamawaki A. Takeda A. Tetrahedron Lett. 1984; 25: 2987
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. Chemisty & Biodiversity 2004; 4: 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 , and references cited therein
4g Chimichi S. Boccalini M. Salvador A. Dall’Acqua F. Basso G. Viola G. ChemMedChem 2009; 4: 769

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 AB. III. Guaciaro MA. Schow SR. Wovkulich PM. Toder BH. Hall TW. J. Am. Chem. Soc. 1981; 103: 219
6c Smith AB. III. Malamas MS. J. Org. Chem. 1982; 47: 3442
6d Taylor MD. Smith AB. III. 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 J. A. Theoduloz C. Z. Naturforsch. 2007; 62b: 275

7a Shao X. Tamm C. Tetrahedron Lett. 1991; 32: 2891
7b Ishikawa M. Ninomiya T. J. Antibiot. 2008; 61: 692
7c Ishikawa M. Ninomiya T. Akabane H. Kushida N. Tsujiuchi G. Ohyama M. Gomi S. Shito K. Murata T. Bioorg. Med. Chem. 2009; 17: 1457

8a Chimichi S. Boccalini M. Cosimelli B. Dall’Acqua F. Viola G. Tetrahedron 2003; 59: 5215
8b Rappai JP. Raman V. Unnikrishnan PA. Prathapan S. Thomas SK. Paulose CS. Bioorg. Med. Chem. Lett. 2009; 19: 764

9 Mack RA. Zazulak WI. Radov LA. Baer JE. Stewart JD. Elzer PH. Kinsolving CR. Georgiev VS. J. Med. Chem. 1988; 31: 1910

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 Carotti A. Carrieri A. Chimichi S. Boccalini M. Cosimelli B. Gnerre C. Carotti A. Carrupt P.-A. Testa B. Bioorg. Med. Chem. Lett. 2002; 12: 3551
12 Woollard JMcK. R. Perry NB. Weavers RT. van Klink JW. Phytochemistry 2008; 69: 1313
13 Smith AB. III. Levenberg PA. Jerris PJ. Scarborough RM. Jr. Wovkulich PM. J. Am. Chem. Soc. 1981; 103: 1501
14 Winkler JD. Oh K. Asselin SM. Org. Lett. 2005; 7: 387

15a Kato K. Nouchi H. Ishikura K. Takaishi S. Motodate S. Tanaka H. Okudaira K. Mochida T. Nishigaki R. Shigenobu K. Akita H. Tetrahedron 2006; 62: 2545
15b Gogoi S. Argade NP. Tetrahedron 2006; 62: 2999

16 Chen K. Shi G. Zhang W. Li H. Wang C. J. Am. Chem. Soc. 2016; 138: 14198
17 He H. Qi C. Hu X. Ouyang L. Xiong W. Jiang H. J. Org. Chem. 2015; 80: 4957

18a Inagaki S. Ukaku M. Chiba A. Takahashi F. Yoshimi Y. Morita T. Kawano T. J. Org. Chem. 2016; 81: 8363
18b Inagaki S. Nakazato M. Fukuda N. Tamura S. Kawano T. J. Org. Chem. 2017; 82: 5583
18c Inagaki S. Sato A. Sato H. Tamura S. Kawano T. Tetrahedron Lett. 2017; 58: 4872

19 Zhou J. Bai L. Liang G. Chen Y. Gan Z. Wang W. Zhoua H. Yu Y. RSC Adv. 2017; 7: 39885

20a Kirsch SF. Binder JT. Liebért C. Menz H. Angew. Chem. Int. Ed. 2006; 45: 5878
20b Binder TJ. Crone B. Kirsch SF. Liébert C. Menz H. Eur. J. Org. Chem. 2007; 1636
20c Bunnelle EM. Smith CR. Lee SK. Singaram SW. Rhodes AJ. Sarpong R. Tetrahedron 2008; 64: 7008
20d Silva F. Reiter M. Mills-Webb R. Sawicki M. Klar D. Bensel N. Wagner A. Gouverneur V. J. Org. Chem. 2006; 71: 8390
20e Marson CM. Edaan E. Morrell JM. Coles SJ. Hursthouse MB. Davies DT. Chem. Commun. 2007; 2494
20f Liu Y. Liu M. Guo S. Tu H. Zhou Y. Gao H. Org. Lett. 2006; 8: 3445
20g Egi M. Azechi K. Saneto M. Shimizu K. Akai S. J. Org. Chem. 2010; 75: 2123

21a Trofimov BA. Shemyakina OA. Mal’kina AG. Ushakov IA. Kazheva ON. Alexandrov GG. Dyachenko OA. Org. Lett. 2010; 12: 3200
21b Shemyakina OA. Mal’kina AG. Nosyreva VV. Ushakov IA. Trofimov BA. ARKIVOC 2012; (viii): 319
21c Shemyakina OA. Stepanov AV. Volostnykh OG. Mal’kina AG. Ushakov IA. Trofimov BA. Russ. J. Org. Chem. 2014; 50: 1617
21d Mal’kina AG. Volostnykh OG. Petrushenko KB. Shemyakina OA. Nosyreva VV. Ushakov IA. Trofimov BA. Tetrahedron 2013; 69: 3714
21e Mal’kina AG. Volostnykh OG. Stepanov AV. Ushakov IA. Petrushenko KB. Trofimov BA. Synthesis 2013; 45: 3435
21f Trofimov BA. Stepanov AV. Mal’kina AG. Volostnykh OG. Shemyakina OA. Ushakov IA. Synth. Commun. 2015; 45: 2718
21g Mal’kina AG. Shemyakina OA. Stepanov AV. Volostnykh OG. Ushakov IA. Sobenina LN. Borodina TN. Smirnov VI. Trofimov BA. Synthesis 2016; 48: 271

22 Amslinger S. Lindner SK. Synthesis 2011; 2671
23 Cao J. Sun K. Dong S. Lu T. Dong Y. Du D. Org. Lett. 2017; 19: 6724

24a Huang A.-C. Chung J.-G. Kuo S.-C. Lu H.-F. Lin T.-P. In Vivo 2007; 21: 227
24b Wands JR. de la Monte S. Aihara A. Olsen MJ. Thomas J.-M. US Patent US9771356 B2, 2017

25a Ward CE. Lo WC. Pomidor PB. Tisdell FE. Ho AW. W. Chiu CL. Tuck DM. Bernando CR. Fong PJ. Omid A. Buteau FA. In Synthesis and Chemistry of Agrochemicals, ACS Symposium Series No. 35. Baker DR. Fenyes JG. Moberg WK. Barrington C. American Chemical Society; Washington DC: 1987: 65-73
25b Sandmann G. Ward CE. Lo WC. Nagy JO. Boeger P. Plant Physiol. 1990; 94: 476
25c Matiadis D. Prousis KC. Igglessi-Markopoulou O. Molecules 2009; 14: 3914

26 Sheldrick GM. Acta Crystallogr., Sect. D 2008; 64: 112

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