Synthesis of New Tetrazol-5-ylalkenyl Derivatives of Ferrocene by Wittig Olefination

Abstract

An effective and straightforward method has been developed for the synthesis of new olefinic derivatives of ferrocene that contain tetrazole rings. The method is based on condensation of 1-formyl-, 1,1′-diformyl-, or (E)-1-(2-formylvinyl)ferrocene with 1-substituted [(triphenylphosphoranylidene)methyl]-1H-tetrazoles, which are readily prepared by treatment of the corresponding phosphonium salts with aqueous sodium hydroxide. The olefination reaction proceeds in a diastereoselective manner with formation of the corresponding (E)-alkenes or (E,E)-dienes as the exclusive or major products.

Key words

iron - heterocycles - ylides - Wittig reactions - olefination - ferrocenes

• References

• 1a Ferrocene: Homogeneous Catalysis, Organic Synthesis, Materials Science. Togni A, Hayashi T. Wiley-VCH; Wenheim: 1995
• 1b Debroy P, Roy S. Coord. Chem. Rev. 2007; 251: 203
• 2a Pal SK, Krishnan A, Das PK, Samuelson AG. J. Organomet. Chem. 2000; 604: 248
• 2b Fuentealba M, Hamon J.-R, Carrillo D, Manzur C. New J. Chem. 2007; 31: 1815
• 3 Ferrocenes: Ligands, Materials and Biomolecules. Stepnicka P. Wiley; Chichester: 2008
• 4 Li M, Cai P, Duan Ch, Lu F, Xie J, Meng Q. Inorg. Chem. 2004; 43: 5174
• 5 Miller JS, Epstein AJ. Angew. Chem. Int. Ed. 1994; 33: 385
• 6 Gao JM, Wang L, Yu HJ, Xiao AG, Ding WB. Propellants, Explos., Pyrotech. 2011; 36: 404
• 7 van Staveren DR, Metzler-Nolte N. Chem. Rev. 2004; 104: 5931
• 8a Bioorganometallics: Biomolecules, Labeling, Medicine. Jaouen G. Wiley-VCH; Weinheim: 2006
• 8b Ornelas C. New J. Chem. 2011; 35: 1973
• 9a Biot C, Glorian G, Maciejewski LA, Brocard JS, Domarle O, Blampain G, Millet P, Georges AJ, Abessolo H, Dive D, Lebibi J. J. Med. Chem. 1997; 40: 3715
• 9b Biot C, Chavain N, Dubar F, Pradines B, Trivelli X, Brocard J, Fortfar I, Dive D. J. Organomet. Chem. 2009; 694: 845
• 10 Chohan ZH, Praveen M. Met.-Based Drugs 1999; 6: 149
• 11 Jaouen G, Vessieres A, Butler I. Acc. Chem. Res. 1993; 26: 361
• 12a Liu J, Liu T, Dai H, Jin Z, Fang J. Appl. Organomet. Chem. 2006; 20: 610
• 12b Snegur LV, Nekrasov YS, Sergeeva NS, Zhilina ZV, Gumenyuk VV, Starikova ZA, Simenel AA, Morozova NB, Sviridova IK, Babin VN. Appl. Organomet. Chem. 2008; 22: 139
• 13a Ganesh V, Sudhir VS, Kundu T, Chandrasekaran S. Chem.–Asian J. 2011; 6: 2670
• 13b Hillard EA, Jaouen G. Organometallics 2011; 30: 20
• 14 Weiss S, Keller M, Bernhardt G, Buschauer A, Knig B. Bioorg. Med. Chem. 2008; 16: 9858
• 15 Mochida T, Shimizu H, Suzuki S, Akasaka T. J. Organomet. Chem. 2006; 691: 4882
• 16 Acikalin S.; Thesis; Middle East Technical University; Ankara (Turkey), 2003; (http://etd.lib.metu.edu.tr/upload/1081256/index.pdf; accessed July 11, 2012)
• 17 Rodriguez JG, Lafuente A. ARKIVOC 2007; (xvi): 195
• 18 Perrin DD, Armango WL. F. Purification of Laboratory Chemicals . Pergamon; New York: 1988. 3rd ed
• 19 Harvill EK, Herbst RM, Schreiner EG. J. Org. Chem. 1952; 17: 1597
• 20 Uchida M, Kowatsu M, Morita S, Kanbe T, Nakagawa K. Chem. Pharm. Bull. 1989; 37: 322
• 21a Sanchez JP, Mich TF, Huang GG. J. Heterocycl. Chem. 1994; 31: 297
• 21b Baraldi PG, Preti D, Tabrizi MA, Fruttarolo F, Saponaro G, Baraldi S, Romagnoli R, Moorman AR, Gessi S, Varani K, Borea PA. Bioorg. Med. Chem. 2007; 15: 2514
• 22 Buzilova CR, Shul’gina VM, Sakovich GV, Vereshchagin LI. Chem. Heterocycl. Compd. 1981; 17: 960
• 23 Ramírez-López P, Sierra MA, Gómez-Gallego M, Mancheño MJ, Gornitzka H. Organometallics 2003; 22: 5092
• 24 Hashimoto T, Kawano Y, Natsume S, Tanaka T, Watanabe T, Nagano M, Sugawara S, Miyadera T. Chem. Pharm. Bull. 1978; 26: 1803