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Synthesis 2004(6): 0949-0959
DOI: 10.1055/s-2004-822332
DOI: 10.1055/s-2004-822332
PAPER
© Georg Thieme Verlag Stuttgart · New York
Inverse Electron Demand Diels-Alder Reactions of Heterodienes Catalyzed by Potassium Hydrogen Sulfate: Diastereoselective, One-Pot Synthesis of Pyranobenzopyrans, Furanobenzopyrans and Tetrahydroquinolines Derivatives
Weitere Informationen
Received
3 November 2003
Publikationsdatum:
13. April 2004 (online)
Publikationsverlauf
Publikationsdatum:
13. April 2004 (online)
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Abstract
Potassium hydrogen sulfate catalyzes the one-pot three components coupling of aldehydes, anilines, and electron rich dienophiles such as dihydropyran, dihydrofuran, ethyl vinylether, and cyclopentadiene. With o-hydroxybenzaldehyde, the reaction probably proceeds through the formation of o-quinonemethide intermediate, which subsequently undergoes cycloaddition with cyclic and acyclic enol ethers leading to the formation of respective chromanes. However, in case of benzaldehydes with no o-hydroxy group, the imine formed acts as the heterodiene and leads to the formation of tetrahydroquinolines.
Keywords
heterodienes - potassium hydrogen sulfate - pyranobenzopyrans - furanobenzopyrans - tetrahydroquinolines
-
1a
Schweizer EE.Meeder-Nycz O. In Chromenes Chromanes ChromonesEllis GP. Wiley-Inter-science; New York: 1977. p.11-139 -
1b
Bowers WS.Ohta T.Cleere JS.Marsella PA. Science 1976, 193: 542 - 2
Hepworth J. Comprehensive Heterocyclic Chemistry Vol. 3:Katritzky AR.Rees CW. Pergamon; Oxford: 1984. p.737 -
3a
Rovnyak GC.Ahmed SZ.Ding CZ.Dzwonczyk S.Ferrara FN.Humphreys WG.Grover GJ.Santafinos D.Atwal KS.Baird AJ.McLaughin LG.Normandin DE.Sleph PG.Traeger SC. J. Med. Chem. 1997, 40: 24 -
3b
Evans JM.Fake CS.Hamilton TC.Poyser RH.Watts EA. J. Med. Chem. 1983, 26: 1582 -
3c
Buckle DR.Arch JRS.Fenwick AE.Hough-Frydrych CSV.Pinto IL.Smith DG.Taylor SG.Tedder . J. Med. Chem. 1990, 33: 3028 - 4
Perry NB.Blunt JW.McCombs JD.Munro MHG. J.Org.Chem. 1986, 51: 5476 - 5
Perry NB.Blunt JW.Munro MHG. Tetrahedron 1988, 44: 1727 - 6
Perry NB.Blunt JW.Munro MHG.Sakai R. J. Org. Chem. 1988, 53: 4127 - 7
Konishi M.Zercher CK.Bechkam S.Haubold E.-M. J. Am. Chem. Soc. 1990, 112: 3715 - 8
Wender PA.Zercher CK.Bechkam S.Haubold E.-M. J. Org. Chem. 1993, 58: 5867 - 9
Uchida M.Chihiro M.Morita S.Kanbe T.Yamashita H.Yamasakai K.Yabuuchi Y.Nakagawa K. Chem. Pharm. Bull. 1989, 37: 2109 - 10
Miller KE.Huang C.-T.Portlock DE.Wright GC. Life Sci. 1987, 40: 63 - 11
Atwal K. inventors; Eur. Pat. EP 488,616. - 12
Carling RW.Leeson PD.Mosely AM.Smith JD.Saywell K.Tricklebank MD.Kemp JA.Marshal GR.Foster AC.Grimwood S. Bioorg. Med. Chem. Lett. 1993, 3: 65 - 13
Tsushima K.Osumi T.Matsuo N.Itaya N. Agricult. Biol. Chem. 1989, 53: 2529 - 14
Evans S. inventors; Eur. Pat. EP 497,735. - 15
Shikhaliev KhS.Shmyreva ZhV.Gurova EM. Izv.Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1989, 32: 85 - 16
Ramesh M.Mohan PA.Shanmugam P. Tetrahedron 1984, 40: 4041 - 17
Nesterova IN.Alekseeva LM.Andreeva LM.Andreeva NI.Golovira SM.Granic VG. Khim.-Farm. Zh. 1995, 29: 31 ; Chem. Abstr. 1996, 128, 117128 - 18
Yamada N.Kadowaki S.Takahashi K.Umezu K. Biochem. Pharmacol. 1992, 44: 1211 - 19
Faber K.Stueckler H.Kappe T. J. Heterocycl. Chem. 1984, 21: 1177 - 20
Akhmed Khodzhaeva KS.Bessonova IA. Dokl. Akad. Nauk Uzh. SSR 1982, 34 ; Chem. Abstr., 1983, 98: 83727 -
21a
Jurd L.Wong RV. Aust. J. Chem. 1981, 34: 1625 -
21b
Coppola GM. J. Heterocycl. Chem. 1983, 20: 1217 - 22
Wildman WC. Alkaloids 1960, 6: 289 ; and references therein - 23
Lucchini V.Prato M.Scorrano G.Tecilla P. J. Org. Chem. 1998, 53: 2251 - 24
Miyazaki H.Honda K.Asami M.Inhouse S. J. Org. Chem. 1999, 64: 9507 - 25
Ma Y.Qian C.Xie M.Sun J. J. Org. Chem. 1999, 64: 6462 - 26
Grieco PA.Bahsas A. Tetrahedron Lett. 1998, 29: 5855