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Synthesis 2010(24): 4207-4212
DOI: 10.1055/s-0030-1258311
DOI: 10.1055/s-0030-1258311
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkIron/Palladium-Catalyzed Intramolecular Hydroamination: An Expedient Synthesis of Pyrrole-Annulated Coumarin and Quinolone Derivatives
Weitere Informationen
Received
30 August 2010
Publikationsdatum:
21. Oktober 2010 (online)
Publikationsverlauf
Publikationsdatum:
21. Oktober 2010 (online)

Abstract
A highly efficient intramolecular hydroamination reaction of heterocycle-centered aminoalkynes using both substituted and free amines catalyzed by PdCl2/FeCl3 catalytic system to form the biologically important pyrrolocoumarin and pyrroloquinolone derivatives is reported. The use of both aliphatic and aromatic substituted alkynes with different heterocyclic skleton in this strategy demonstrated the diversity of this method.
Key words
hydroamination - pyrrolocoumarin - pyrroloquinolone - FeCl3 - aminoalkynes
- 1a
Glasby JS. Encyclopedia of Alkaloids Plenum Press; New York: 1975.Reference Ris Wihthout Link - 1b
Cacchi S.Fabrizi G. Chem. Rev. 2005, 105: 2873Reference Ris Wihthout Link - 1c
Li JJ.Gribble GW. Palladium in Heterocyclic Chemistry Pergamon; Oxford: 2000. Chap. 3.Reference Ris Wihthout Link - 1d
Somei M.Yamada F. Nat. Prod. Rep. 2005, 22: 73Reference Ris Wihthout Link - 2a
Arcadi A.Bianchi G.Marinelli F. Synthesis 2004, 610Reference Ris Wihthout Link - 2b
Zhang Y.Donahue JP.Li C.-J. Org. Lett. 2007, 9: 627Reference Ris Wihthout Link - 2c
Sakai N.Annaka K.Konakahara T. Tetrahedron Lett. 2006, 47: 631Reference Ris Wihthout Link - 2d
Namba K.Nakagawa Y.Yamamoto H.Imagawa H.Nishizawa M. Synlett 2008, 1719Reference Ris Wihthout Link - 2e
Li X.Chianese AR.Vogel T.Crabtree RH. Org. Lett. 2005, 7: 5437Reference Ris Wihthout Link - 3a
Hagen SE.Domagala JM.Heifetz CL.Sanchez JP.Solomon M. J. Med. Chem. 1990, 33: 849Reference Ris Wihthout Link - 3b
Raski SR.Williams RM. Chem. Rev. 1998, 98: 2723Reference Ris Wihthout Link - 3c
Murakami A.Gao G.Omura M.Yano M.Ito C.Furukawa H.Takahasi D.Koshimizu K.Ohigash H. Biorg. Med. Chem. Lett. 2000, 10: 59Reference Ris Wihthout Link - 3d
Laborde E.Kiely JS.Culbertson TP.Lesheski LE. J. Med. Chem. 1993, 36: 1964Reference Ris Wihthout Link - 4a
Dickinson JM. Nat. Prod. Rep. 1993, 10: 71Reference Ris Wihthout Link - 4b
Piorung MC.Blume F. J. Org. Chem. 1999, 64: 3642Reference Ris Wihthout Link - 4c
Boyd DR.Sharma ND.Barr SA.Carroll JG.Mackerracher D.Malone JF. J. Chem. Soc., Perkin Trans. 1 2000, 3397Reference Ris Wihthout Link - 5a
Rodighiero P.Chilin A.Pastorini G.Guiotto A.
J. Heterocycl. Chem. 1987, 24: 1041Reference Ris Wihthout Link - 5b
Guiotto A.Chilin A.Manzini P.Dall’Acqua F.Bordin F.Rodighiero P. Farmaco 1995, 50: 479Reference Ris Wihthout Link - 6
Gia O.Mobilio S.Chilin A.Rodghiero P.Palumbo M. J. Photochem. Photobiol., B. 1988, 2: 435 - 7
Quanten E.Adriaens P.Schryver FC.Roelandts R.Degreef H. Photochem. Photobiol. 1986, 43: 485 - 8
Kontogiorgis C.Litinas KE.Makri A.Nicolaides DN.Vronteli A.Litina DJH.Pontiki E.Siohou A.
J. Enzyme Inhib. Med. Chem. 2008, 23: 43 - 9
Chen L.Hu T.-S.Yao Z.-J. Eur. J. Org. Chem. 2008, 36: 6175 - 10
Chen L.Xu MH. Adv. Synth. Catal. 2009, 351: 2005 - 11a
Ridley CP.Reddy MVR.Rocha G.Bushman FD.Faulknera DJ. Bioorg. Med. Chem. 2002, 10: 3285Reference Ris Wihthout Link - 11b
Fan H.Peng J.Hamann MT.Hu JH. Chem. Rev. 2008, 108: 264Reference Ris Wihthout Link - 11c
Yamaguchi T.Fukuda T.Ishibashi F.Iwao M. Tetrahedron Lett. 2006, 47: 3755Reference Ris Wihthout Link - 11d
Tardy C.Facompre M.Laine W.Baldeyrou B.Garcia-Gravalos D.Francesch A.Mateo C.Pastor A.Jimenez JA.Manzanares I.Cuevasb C.Bailly C. Bioorg. Med. Chem. 2004, 12: 1697Reference Ris Wihthout Link - 12a
Jiang W.Alford VC.Qiu Y.Bhattacharjee S.John TM.Johnson DH.Kraft PJ.Lundeen SG.Sui Z. Bioorg. Med. Chem. 2004, 12: 1505Reference Ris Wihthout Link - 12b
Yamashkin SA.Yudin LG.Kost AN. Chem. Heterocycl. Compd. (Engl. Transl.) 1983, 19: 401Reference Ris Wihthout Link - 13
Ho TCT.Jones K. Tetrahedron 1997, 53: 8287 - 14a
Majumdar KC.Mondal S.De N. Synlett 2008, 2851Reference Ris Wihthout Link - 14b
Majumdar KC.Mondal S.De N. Synthesis 2009, 2385Reference Ris Wihthout Link - 14c
Majumdar KC.Chattopadhyay B.Samanta S. Synthesis 2009, 311Reference Ris Wihthout Link - 14d
Majumdar KC.Chakravorty S.De N. Tetrahedron Lett. 2008, 49: 3419Reference Ris Wihthout Link - 14e
Majumdar KC.Samanta S.Chattopadhyay B. Tetrahedron Lett. 2008, 49: 7213Reference Ris Wihthout Link - 15a
Tang Z.-Y.Hu O.-S. Adv. Synth. Catal. 2006, 348: 846Reference Ris Wihthout Link - 15b
Kaspar LT.Ackermann L. Tetrahedron 2005, 61: 11311Reference Ris Wihthout Link - 15c
Yasuhara A.Takeda Y.Naoyuki S.Sakamoto T. Chem. Pharm. Bull. 2002, 50: 235Reference Ris Wihthout Link - 16a
Zhang Y.Donahue JP.Li C.-J. Org. Lett. 2007, 9: 627Reference Ris Wihthout Link - 16b
Kurisaki T.Naniwa T.Yamamoto H.Imagawa H.Nishizawa M. Tetrahedron Lett. 2007, 48: 1871Reference Ris Wihthout Link - 16c
Hiroya K.Itoh S.Ozawa M.Kanamori Y.Sakamoto T. Tetrahedron Lett. 2002, 43: 1277Reference Ris Wihthout Link - 16d
Yin Y.Chai Z.Ma W.-Y.Zhao G. Synthesis 2008, 4036Reference Ris Wihthout Link - 16e
Trost BM.McClory A. Angew. Chem. Int. Ed. 2007, 46: 2074Reference Ris Wihthout Link - 16f
Cariou K.Ronan B.Mignani S.Fensterbank L.Malacria M. Angew. Chem. Int. Ed. 2007, 46: 1881Reference Ris Wihthout Link - 17
Koradin C.Dohale W.Rodriguez AL.Schmidt B.Knochel P. Tetrahedron 2003, 59: 1571 - 18
Terrasson V.Michaux J.Gaucher A.Wehbe J.Marque S.Prim D.Campagne J.-M. Eur. J. Org. Chem. 2007, 35: 5332 - 19
Liang Y.Tang S.Zhang X.-D.Mao L.-Q.Xie Y.-X.Li J.-H. Org. Lett. 2006, 8: 3017 - 20
Tang S.Xie Y.-X.Li J.-H.Wang N.-X. Synthesis 2007, 1841 - 21
Baldwin JE. J. Chem. Soc., Chem. Commun. 1976, 734