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-00000084.xml
Synthesis 2013; 45(10): 1341-1348
DOI: 10.1055/s-0033-1338299
DOI: 10.1055/s-0033-1338299
paper
KF/Al2O3/PEG-400: An Efficient Catalytic System for the Fiesselmann-Type Synthesis of Thiophene Derivatives
Weitere Informationen
Publikationsverlauf
Received: 01. Februar 2013
Accepted after revision: 11. März 2013
Publikationsdatum:
28. März 2013 (online)
Abstract
A simple and mild protocol has been developed for the synthesis of novel steroidal and nonsteroidal thiophene derivatives from β-halo-α,β-unsaturated aldehydes using KF/Al2O3/PEG-400 as an efficient catalytic system. The β-halo-α,β-unsaturated aldehydes are synthesized from the corresponding ketones using Vilsmeier formylation reaction and converted into β-halo-α,β-unsaturated nitriles. The synthetic protocol is subsequently applied to the synthesis of 3-aminothiophene derivatives using β-halo-α,β-unsaturated nitriles.
Key words
Fiesselmann synthesis - KF/Al2O3/PEG-400 - thiophene - unsaturated aldehyde - unsaturated nitrileSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Gronowitz S. Thiophene and Its Derivatives, Part 1 . In The Chemistry of Heterocyclic Compounds . Vol. 44. Gronowitz S. Wiley & Sons; New York: 1985: 88
- 2a Chao EC. Drugs Future 2011; 36: 351
- 2b Ruilope L, Jager B, Prichard B. Blood Pressure 2001; 10: 223
- 2c Hirbec H, Gaviria M, Vignon J. CNS Drug Rev. 2001; 7: 172
- 2d Petroski RE, Pomeroy JE, Das R, Bowman H, Yang W, Chen AP, Foster AC. J. Pharmacol. Exp. Ther. 2005; 317: 369
- 2e Bertaina-Anglade V, La Rochelle CD, Scheller DK. Eur. J. Pharmacol. 2006; 548: 106
- 3a Handbook of Oligo- and Polythiophenes . Fichou D. Wiley-VCH; Weinheim: 1999
- 3b Electronic Materials: The Oligomer Approach . Mullen K, Wegner G. Wiley-VCH; Weinheim: 1998
- 3c Hotta S. Molecular Conductive Materials: Polythiophenes and Oligothiophenes. In Handbook of Organic Conductive Molecules and Polymers. Vol. 2. Nalwa HS. Wiley; Chichester: 1997: 309
- 4 Seed A. Chem. Soc. Rev. 2007; 36: 2046 ; and references cited therein
- 5a Geiger F, Stoldt M, Schweizer H, Bauerle P, Umbach E. Adv. Mater. (Weinheim, Ger.) 1993; 5: 922
- 5b Garnier F, Hajlaoui R, Yassar A, Srivastava P. Science 1994; 265: 1684
- 5c Sirringhaus H, Kawase T, Fried R, Shimoda T, Inbasekaran M, Wu W, Woo E. Science 2000; 290: 2123
- 5d Ong BS, Wu Y, Liu P, Gardner S. J. Am. Chem. Soc. 2004; 126: 3378
- 5e Noma N, Tsuzuki T, Shirota Y. Adv. Mater. (Weinheim, Ger.) 1995; 7: 647
- 6 Giordanetto F, Karlsson O, Lindberg J, Larsson L.-O, Linusson A, Evertsson E, Morgan DG. A, Inghardt T. Bioorg. Med. Chem. Lett. 2007; 17: 5222
- 7 Kumar PR, Raju S, Goud PS, Sailaja M, Sarma MR, Reddy GO, Kumar MP, Reddy VV. R. M. K, Suresha T, Hegdeb P. Bioorg. Med. Chem. 2004; 12: 1221
- 8 Bonini C, Chiummiento L, Bonis MD, Funicello M, Lupattelli P, Suanno G, Berti F, Campaner P. Tetrahedron 2005; 61: 6580
- 9 Brault L, Migianu E, Néguesque A, Battaglia E, Bagrel D, Kirsch G. Eur. J. Med. Chem. 2005; 40: 757
- 10 Deng H, Hu H, He M, Hu J, Niu W, Ferrie AM, Fang Y. J. Med. Chem. 2011; 54: 7385
- 11 Yapp KE, Hopcraft MS, Parashos P. Br. Dent. J. 2011; 210: 323
- 12 Name Reactions in Heterocyclic Chemistry . Li JJ. John Wiley; New York: 2005
- 13 Louis A, Carpino AA. A.-M, Ionescu D, Mansour EM. E, Zewail MA. J. Org. Chem. 2007; 72: 1729
- 14 Kumar V, Daum SJ, Bell MR, Alexander MA, Christiansen RG, Ackerman JH, Krolski ME, Pilling CM, Herrmann JL. Jr, Winneker RC, Wagner MM. Tetrahedron 1991; 47: 5099
- 15 Mavrova ATs, Wesselinova D, Tsenov YA, Denkova P. Eur. J. Med. Chem. 2009; 44: 63
- 16 Teiber M, Muller TJ. J. Chem. Commun. 2012; 48: 2080
- 17a Leclercq G In Antitumor Steroids . Blickenstaff RT. Academic Press; New York: 1992
- 17b Raus J In Cytotoxic Estrogens in Hormone Receptive Tumors . Raus J, Martens H, Leclercq G. Academic Press; London: 1980
- 17c Singh H, Jindal DP, Yadav MR, Kumar M. Prog. Med. Chem. 1991; 28: 233
- 17d Hirshmann R, Steinberg NG, Buchschacher P, Fried JH, Kent GJ, Tishler M. J. Am. Chem. Soc. 1963; 85: 120
- 18a Posner GH. Angew. Chem., Int. Ed. Engl. 1978; 17: 487
- 18b Kawabata T, Mizugaki T, Ebitani K, Kaneda K. J. Am. Chem. Soc. 2003; 125: 10486
- 18c Agarwal A, Rani S, Vankar YD. J. Org. Chem. 2004; 69: 6137
- 18d Kamata K, Kasai J, Yamaguchi K, Mizuno N. Org. Lett. 2004; 6: 3577
- 19a Blass BE. Tetrahedron 2002; 58: 9301
- 19b Hattori H. Chem. Rev. 1995; 95: 537
- 19c Clark JH, Macquarrie DJ. Chem. Soc. Rev. 1996; 303
- 19d Kabashima H, Tsuji H, Shibuya T, Hattori H. J. Mol. Catal. A: Chem. 2000; 155: 23
- 19e Blass BE, Harris CL, Portlock DE. Tetrahedron Lett. 2001; 42: 1611
- 20 Nelson WM. Green Solvents for Chemistry: Perspectives and Practice . Oxford University Press; New York: 2003
- 21a Bezbaruah P, Gogoi J, Rao KS, Gogoi P, Boruah RC. Tetrahedron Lett. 2012; 53: 4389
- 21b Gogoi J, Bezbaruah P, Saikia P, Goswami J, Gogoi P, Boruah RC. Tetrahedron Lett. 2012; 53: 1497
- 21c Gogoi S, Shekarrao K, Duarah A, Bora TC, Gogoi S, Boruah RC. Steroids 2012; 77: 1438
- 22 Shie J.-J, Fang J.-M. J. Org. Chem. 2003; 68: 1158
- 23 Weinstock LM, Stevenson JM, Tomellini RB, Reinhold DF. Tetrahedron Lett. 1986; 27: 3845
- 24a Ando T, Brown SJ, Clark J, Cork HD. G, Hanafusa T, Ichihara J, Miller JM, Robertson MS. J. Chem. Soc., Perkin Trans. 2 1986; 1133
- 24b Ando T, Clark JH, Cork DG, Hanafusa T, Ichihara J, Kimura T. Tetrahedron Lett. 1987; 28: 1421
- 25 Wen L, Ji C, Li Y, Li M. J. Comb. Chem. 2009; 11: 799