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Synthesis 2011(13): 2079-2084
DOI: 10.1055/s-0030-1260056
DOI: 10.1055/s-0030-1260056
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkFacile Synthesis of Tricyclic Oxazino- or Oxazepino-Fused Tetrahydroquinolines via Intramolecular Reductive Amidation
Further Information
Received
11 January 2011
Publication Date:
19 May 2011 (online)
Publication History
Publication Date:
19 May 2011 (online)
Abstract
Reductive cyclization of ω-(8-quinolyloxy)alkyl esters by zinc in acetic acid is shown to constitute a convenient methodology for the synthesis of oxazino- or oxazepino-fused tetrahydroquinolines. It is operationally simple, requires a short reaction time, and provides excellent yields.
Key words
reductive amidation - intramolecular amidation - ω-(8-quinolyloxy)alkyl ester - fused tetrahydroquinoline - zinc
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Czarnik AW. Acc. Chem. Res. 1996, 29: 112 - 2
Fagnoni M. Heterocycles 2003, 60: 1921 - 3
Hazos G.Riedl Z.Kollenz G. Eur. J. Org. Chem. 2001, 3405 - 4
Majumdar KC.Basu PK.Mukhopadhyay PP. Tetrahedron 2004, 60: 6239 - 5
Barchechath SD.Tawatao RI.Corr M.Carson DA.Cottam HB. Bioorg. Med. Chem. Lett. 2005, 15: 1785 - 6
Brana MF.Cacho M.Gradillas A.Pascual-Teresa B.Ramos A. Curr. Pharm. Des. 2001, 7: 1745 - 7
Martinez R.Chacon-Garcia L. Curr. Med. Chem. 2005, 12: 127 - 8
White JD.Yager KM.Yakura T. J. Am. Chem. Soc. 1994, 116: 1831 - 9
Tsushima K.Osumi T.Matsuo N.Itaya N. Agric. Biol. Chem. 1989, 53: 2529 - 10
Nishiyama T.Hashiguchi Y.Sakata T.Sakaguchi T. Polym. Degrad. Stab. 2003, 79: 225 - 11
Shikhaliev KS.Shmyreva Z.Gurova EM. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Technol. 1989, 32: 85 ; Chem. Abstr. 1990, 112, 216659a - 12a
Hashimoto K.Okaichi Y.Nomi D.Miyamoto H.Bando M.Kido M.Fujimura T.Furuta T.Minamikawa J.-I. Chem. Pharm. Bull. 1996, 44: 642Reference Ris Wihthout Link - 12b
Shaaban MA.Ghoneim KM.Kalifa M. Pharmazie 1997, 32: 90Reference Ris Wihthout Link - 12c
Collin J.Jaber N.Lannou MI. Tetrahedron Lett. 2001, 42: 7405Reference Ris Wihthout Link - 13a
Dutta R.Mandal D.Panda N.Mondal NB.Banerjee S.Kumar S.Weber M.Luger P.Sahu NP. Tetrahedron Lett. 2004, 45: 9361Reference Ris Wihthout Link - 13b
Paira P.Hazra A.Sahu KB.Banerjee S.Mondal NB.Sahu NP.Weber M.Luger P. Tetrahedron 2008, 64: 4026Reference Ris Wihthout Link - 13c
Paira P.Paira R.Hazra A.Naskar S.Sahu KB.Saha P.Mondal S.Maity A.Banerjee S.Mondal NB. Tetrahedron Lett. 2009, 50: 4619Reference Ris Wihthout Link - 13d
Paira P.Paira R.Hazra A.Sahu KB.Naskar S.Saha P.Mondal S.Maity A.Banerjee S.Mondal NB. Tetrahedron Lett. 2009, 50: 5505Reference Ris Wihthout Link - 14
Kaufman D.Johnson E.Mosher MD. Tetrahedron Lett. 2005, 46: 5613 - 15
Da Costa CSJ.Pais KC.Fernandes EL.de Oliveira PSM.Mendonça JS.De Souza MVN.Peralta MA.Vasconcelos TRA. ARKIVOC 2006, (i): 128 - 16
Ranu BC.Jana U.Sarkar A. Synth. Commun. 1998, 28: 485 - 17
Tafel J. Ber. Dtsch. Chem. Ges. 1894, 27: 825 - 18
Kocian O.Ferles M. Collect. Czech. Chem. Commun. 1978, 43: 1413 - 19
Gauffre JC.Grignon-Dubois M.Rezzonico B.Léger M. J. Org. Chem. 2002, 67: 4696 - 20
Zhuravleva AYu.Zimichev VA.Zemtsova NM.Klimochkin NYu. Russ. J. Org. Chem. (Engl. Transl.) 2009, 45: 609