Synthesis, Inhaltsverzeichnis Synthesis 2012; 44(18): 2964-2968DOI: 10.1055/s-0032-1316735 paper © Georg Thieme Verlag Stuttgart · New York Regioselective Thorpe–Ziegler Cyclization of 3-O-Alkylated Thiophenes; Access to Aminothieno[3,2-b]furans and Aminothieno[3,4-b]furans Charlène Gadais Université de Lorraine, Laboratoire d’Ingénierie Moléculaire et Biochimie Pharmacologique, SRSMC-UMR7565, Institut Jean Barriol FR CNRS 2843, 1 Boulevard Arago, 57070 Metz Technopôle, France, Fax: +33(3)87325801 eMail: stephanie.hesse@univ-lorraine.fr , Stéphanie Hesse* Université de Lorraine, Laboratoire d’Ingénierie Moléculaire et Biochimie Pharmacologique, SRSMC-UMR7565, Institut Jean Barriol FR CNRS 2843, 1 Boulevard Arago, 57070 Metz Technopôle, France, Fax: +33(3)87325801 eMail: stephanie.hesse@univ-lorraine.fr , Gilbert Kirsch Université de Lorraine, Laboratoire d’Ingénierie Moléculaire et Biochimie Pharmacologique, SRSMC-UMR7565, Institut Jean Barriol FR CNRS 2843, 1 Boulevard Arago, 57070 Metz Technopôle, France, Fax: +33(3)87325801 eMail: stephanie.hesse@univ-lorraine.fr › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A two-step synthesis of polyfunctionalized aminothieno[3,2-b]furans and aminothieno[3,4-b]furans is described and discussed. It was found that O-alkylated thiophenes bearing electron-withdrawing groups in the ortho-position undergo condensation in the presence of an excess of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Furthermore, selective condensation on an ortho-nitrile substituent in preference to ortho-ester or ortho-ketone substituents was observed. Key words Key wordsthienofurans - thiophenes - O-alkylation - Thorpe–Ziegler - condensation Volltext Referenzen References 1 Liu M.-G, Hu Y.-G, Ding M.-W. Tetrahedron 2008; 64: 9052 2 Mashraqui SH, Ghadigaonkar S, Ashraf M, Sri Ranjini A, Ghosh S, Das PK. Tetrahedron 2007; 63: 10011 3 Metri N, Sallenave X, Beouch L, Plesse C, Goubard F, Chevrot C. Tetrahedron Lett. 2010; 51: 6673 4 Nakayama J, Dong H, Sawada K, Ishii A, Kumakura S. Tetrahedron 1996; 52: 471 5 Prugh JD, Hartman GD, Mallorga PJ, McKeever BM, Michelson SR, Murcko MA, Schwam H, Smith RL, Sondey JM, Springer JP, Sugrue MF. J. Med. Chem. 1991; 34: 1805 6 Prugh JD, Gould RJ, Lynch RJ, Zhang G, Cook JJ, Holahan MA, Stranieri MT, Sitko GR, Gaul SL, Bednar RA, Bednar B, Hartman GD. Bioorg. Med. Chem. Lett. 1997; 7: 865 7 Balamurugan K, Perumal S, Reddy AS. K, Yogeeswari P, Sriram D. Tetrahedron Lett. 2009; 50: 6191 8 Moretto AF, Kirincich SJ, Xu WX, Smith MJ, Wan Z.-K, Wilson DP, Follows BC, Binnun E, Joseph-McCarthy D, Foreman K, Erbe DV, Zhang YL, Tam SK, Tama SY, Lee J. Bioorg. Med. Chem. 2006; 14: 2162 9 Kumar A, Bokria JG, Buyukmumcu Z, Dey T, Sotzing GA. Macromolecules 2008; 41: 7098 10 Sotzing GA. US Patent 0326187A1, 2009 11 Radwan SM, Bakhite EA. Monatsh. Chem. 1999; 130: 1117 12 Sugiyama H, Yoshida M, Mori K, Kawamoto T, Sogabe S, Takagi T, Oki H, Tanaka T, Kimura H, Ikeura Y. Chem. Pharm. Bull. 2007; 55: 613 13 Prevysh-Kvinto A. Chem. Heterocycl. Compd. 1994; 661 14 Dey T, Navarathne D, Invernale MA, Berghorn ID, Sotzing GA. Tetrahedron Lett. 2010; 51: 2089 15 Banks MR, Barker JM, Huddleston PR. J. Chem. Soc., Perkin Trans. 1 1986; 2223 16 Takao S, Hideki K, Akiko K. Synthesis 1995; 87 17 Buttery JH, Moursounidis J, Wege D. Aust. J. Chem. 1995; 48: 593 18 Hergué N, Mallet C, Touvron J, Allain M, Leriche P, Frère P. Tetrahedron Lett. 2008; 49: 2425 19 Jiri S, Miloslav N, Jaroslav P. Collect. Czech. Chem. Commun. 1993; 2983 20 Sommen G, Comel A, Kirsch G. Synthesis 2003; 735 21 Gronowitz S, Hornfeldt AB. Thiophene and Its Derivatives . In The Chemistry of Heterocyclic Compounds . Part 3, Vol. 44 Wiley & Sons; New York: 1986. Chap. 1, 73 22 Shirinian VZ, Shimkin AA, Tipikin SN, Krayushkin MM. Synthesis 2009; 3803 23 Hunter GA, McNab H. New J. Chem. 2010; 34: 2558 24 Krayushkin MM, Shirinian VZ, Nikalin DM, Shimkin AA. Russ. Chem. Bull., Int. Ed. 2004; 53: 631
