RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2014; 25(12): 1713-1716
DOI: 10.1055/s-0034-1378276
DOI: 10.1055/s-0034-1378276
letter
Decarboxylative Knoevenagel-Type Reactions on Tetronamides: Synthesis of 5-Ylidene-4-Amino-2(5H)-Furanones
Weitere Informationen
Publikationsverlauf
Received: 11. April 2014
Accepted after revision: 11. Mai 2014
Publikationsdatum:
06. Juni 2014 (online)
Abstract
A detailed account regarding the synthesis of 5-ylidene-2(5H)-furanones is given. The key step is a decarboxylative Knoevenagel-type reaction of tetronamides with various α-functionalized aldehydes. The synthesis of protected basidalin is presented.
-
References and Notes
- 1a Schlessinger RH, Yu YJ. J. Am. Chem. Soc. 1996; 118: 3301
- 1b Clark JS, Marlin F, Nay B, Wilson C. Org. Lett. 2003; 5: 89
- 1c Samaritani S, Bruyère H, Ballereau S, Royer J. C. R. Chimie 2005; 8: 841
- 1d Bruyère H, Dos Reis C, Samaritani S, Ballereau S, Royer J. Synthesis 2006; 1673
- 2 For some examples, see: Wang J, Jiang X, Chen M, Ge Z, Hu Y, Hu H. J. Chem. Soc., Perkin Trans. 1 2001; 66
- 3a Zhou L.-H, Yu X.-Q, Pu L. J. Org. Chem. 2009; 74: 2013
- 3b Hertzberg R, Moberg C. J. Org. Chem. 2013; 78: 9174 ; and references cited therein
- 4a Nishide K, Aramata A, Kamanaka T, Inoue T, Node M. Tetrahedron 1994; 50: 8337
- 4b Dankwardt SM, Dankwardt JW, Schlessinger RH. Tetrahedron Lett. 1998; 39: 4971
- 4c Dankwardt SM, Dankwardt JW, Schlessinger RH. Tetrahedron Lett. 1998; 39: 4975
- 4d Dankwardt SM, Dankwardt JW, Schlessinger RH. Tetrahedron Lett. 1998; 39: 4979
- 4e Bruyère H, Ballereau S, Selkti M, Royer J. Tetrahedron 2003; 59: 5879
- 5a Agami C, Amiot F, Couty F, Dechoux L. Tetrahedron Lett. 1998; 39: 5373
- 5b Agami C, Dechoux L, Hebbe S. Synlett 2001; 1440
- 5c Agami C, Dechoux L, Hebbe S, Moulinas J. Synthesis 2002; 79
- 5d Agami C, Dechoux L, Hamon L, Hebbe S. Synthesis 2003; 859
- 5e Banide E, Lemau de Talance V, Schmidt G, Lubin H, Comesse S, Dechoux L, Hamon L, Kadouri-Puchot C. Eur. J. Org. Chem. 2007; 4517
- 6a Agami C, Dechoux L, Ménard C, Hebbe S. J. Org. Chem. 2002; 67: 7573
- 6b Alladoum J, Dechoux L. Tetrahedron Lett. 2005; 46: 8203
- 6c Alladoum J, Toum V, Hebbe S, Kadouri-Puchot C, Dechoux L. Tetrahedron Lett. 2009; 50: 617
- 7 Toum V, Kadouri-Puchot C, Hamon L, Lhommet G, Mouriès-Mansuy V, Vanucci-Bacqué C, Dechoux L. Synthesis 2011; 2781
- 8a Moore HW, Shelden R, Shellhamer DF. J. Org. Chem. 1969; 34: 1999
- 8b Moore HW, Shelden R, Deters DW, Wikholm RJ. J. Am. Chem. Soc. 1970; 92: 1675
- 8c Moore HW, Hernandez L, Kunert DM, Mercer F, Sing A. J. Am. Chem. Soc. 1981; 103: 1769
- 8d Torres T, Shäfer W. Tetrahedron Lett. 1991; 32: 5825
- 8e Martínez-Díaz MV, Rodríguez-Morgade S, Schäfer W, Torres T. Tetrahedron 1993; 49: 2261
- 8f Armesto D, Rodriguez-Morgade S, Ortiz MJ, Vasquez P, Torres T. Tetrahedron 1997; 53: 3363
- 9 Iinuma H, Nakamura H, Naganawa H, Masuda T, Takano S, Takeuchi T, Umezawa H, Iitaka Y, Obayashi A. J. Antibiot. 1983; 36: 448
- 10a Yamamoto Y, Ohno M, Eguchi S. Tetrahedron 1994; 50: 7783
- 10b For another albeit unsuccessful approach to basidalin see: Hiyama T, Oishi H, Suetsugu Y, Nishide K, Saimoto H. Bull. Chem. Soc. Jpn. 1987; 60: 2139
- 11 Schachtner JE, Stachel HD, Polborn K, Anke T. Eur. J. Med. Chem. 1998; 33: 309
- 12a Knoevenagel E. Ber. Dtsch. Chem. Ges. 1898; 31: 2596
- 12b Doebner O. Ber. Dtsch. Chem. Ges. 1902; 35: 1136
- 13 Collins PM, Overend WG, Shing TS. J. Chem. Soc., Chem. Commun. 1982; 297
- 14a Milite C, Viviano M, Santoriello M, Arico F, Sbardella G, Castellano S. RSC Advances 2012; 2: 5229
- 14b Varadwaj GB. B, Rana S, Parida KM. Dalton Trans. 2013; 42: 5122
- 14c Mohite AR, Bhat RG. Org. Lett. 2013; 15: 4564 ; and references cited therein
- 15a Kemme ST, Smejkal T, Breit B. Adv. Synth. Catal. 2008; 350: 989 ; and references cited therein
- 15b For a recent study concerning the mechanism, see: Bermudez E, Ventura ON, Saenz Mendez P. J. Phys. Chem. 2010; 114: 13086
- 16 List B, Doehring A, Hechavarria Fonseca MT, Wobser K, van Thienen H, Rios Torres R, Llamas Galilea P. Adv. Synth. Catal. 2005; 347: 1558
- 17 Lingjian Z, Ning L, Zhenyuan M, Chunquan S, Chunlin Z, Jianzhong Y, Wannian Z. Chin. J. Chem. 2012; 30: 139
- 18 Suresh Dhruva Kumar D, Sandhu JS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2011; 50: 1479
- 19a Kallikat Augustine J, Naik YA, Mandal AB, Chowdappa N, Praveen VB. J. Org. Chem. 2007; 72: 9854
- 19b Kallikat Augustine J, Naik YA, Poojari S, Chowdappa N, Sherigara BS, Areppa K. Synthesis 2009; 2349
- 20a McNulty J, Steere JA, Wolf S. Tetrahedron Lett. 1998; 39: 8013
- 20b Karchgaudhuri N, De A, Mitra AK. J. Chem. Res. 2002; 180
- 20c Peng Y, Song G. Green Chem. 2003; 5: 704
- 21 Lu J, Toy PH. Synlett 2011; 1723
- 22 Balducci E, Attolino E, Taddei M. Eur. J. Org. Chem. 2011; 311
- 23 Habrant D, Le Roux A, Poigny S, Meunier S, Wagner A, Mioskowski C. J. Org. Chem. 2008; 73: 9490
- 24 We demonstrated by solvent effects in 1H NMR that the 1H NMR chemical shift of the NH proton in (Z)-β-enamino-diesters is downfielded due to an intramolecular hydrogen bond, see: Toum V, Lhommet G, Dechoux L. Synlett 2012; 2349
- 25 Decarboxylated tetronamide 8.
- 26 For a basic dehydrodecarboxylation reaction see: Thorimbert S, Taillier C, Bareyt S, Humilière D, Malacria M. Tetrahedron Lett. 2004; 55: 9123
- 27 Parikh JR, v. Doering WE. J. Am. Chem. Soc. 1967; 89: 5505
- 28 Boyer N, Gloanec P, De Nanteuil G, Jubault P, Quirion JC. Eur. J. Org. Chem. 2008; 4277
- 29 Tanaka T, Oikawa Y, Hamada T, Yonemitsu O. Tetrahedron Lett. 1986; 31: 3651
- 30 Mallinger A, Nadal B, Chopin N, Le Gall T. Eur. J. Org. Chem. 2010; 1142
For cyclizations with NBS, see:
For recent publications concerning the Doebner reaction, see: