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        Synthesis  2011(22): 3692-3696  
DOI: 10.1055/s-0031-1289576
   DOI: 10.1055/s-0031-1289576
PAPER
© Georg Thieme Verlag
      Stuttgart ˙ New YorkSynthesis of Coumarins and Neoflavones through Zinc Chloride Catalyzed Hydroarylation of Acetylenic Esters with Phenols
Weitere Informationen
            
               
                  
                        
                              Received
                              25 July 2011 
                      
Publikationsdatum:
27. Oktober 2011 (online)
            
         
      
   Publikationsverlauf
Publikationsdatum:
27. Oktober 2011 (online)
Abstract
Acetylenic esters react with oxygenated phenols under solvent-free conditions in the presence of only 5 mol% of zinc chloride as a catalyst to give coumarins and neoflavones in reasonable-to-good yields.
Key words
phenols - catalysis - arylations - heterocycles - alkynes - esters
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- 1a 
             
            
Borges F.Roleira F.Milhazes N.Santana L.Uriarte E. Curr. Med. Chem. 2005, 12: 887 - 1b 
             
            
Fylaktakidou KC.Hadjipavlou-Litina DJ.Litinas KE.Nicolaides DN. Curr. Pharm. Des. 2004, 10: 3813 - 1c 
             
            
Lacy A.O’Kennedy R. Curr. Pharm. Des. 2004, 10: 3797 - 2 
             
            
Garazd MM.Garazd YaL.Khilya VP. Chem. Nat. Compd. 2005, 41: 245 - 3a 
             
            
Runkel M.Tegtmeier M.Legrum W. Eur. J. Clin. Pharmacol. 1996, 50: 225 - 3b 
             
            
Rauma A.-L.Rautio A.Pasanen M.Pelkonen O.Torronen R.Mykkanen H. Eur. J. Clin. Pharmacol. 1996, 50: 133 - 3c 
             
            
Pulsford AH.Heywood R.Street AE.Majeed SK. Toxicol. Lett. 1983, 15: 167 - 4a 
             
            
Conforti F.Marrelli M.Menichini F.Bonesi M.Statti G.Rovenzano E.Menichini F. Curr. Drug Ther. 2009, 4: 38 - 4b 
             
            
Via LD.Gia O.Magno SM.Braga A.González-Gómez JC.Pérez-Montoto LG.Uriarte E. Bioorg. Med. Chem. 2010, 5708 - For a review, see:
 - 5a 
             
            
Janssen MJFM.van der Meulen J. Neth. J. Med. 1996, 48: 198 - 5b 
             
            
Chen T.Platz MS.Robert M.Savéant J.-M.Marcinek A.Rogowski J.Gebicki J.Zhu Z.Bally T. J. Phys. Chem. A 1997, 101: 2124 - 5c 
             
            
Tablet C.Hillebrand M. J. Photochem. Photobiol., A 2007, 189: 73 - 6a  For
            a history of the discovery of warfarin, see:  
            
Wardrop D.Keeling D. Br. J. Haematol. 2010, 141: 757 - 6b  For a review, see:  
            
Ruff CT.Braunwald E. J. Cardiovasc. Pharmacol. Ther. 2010, 15: 210 - 6c 
             
            
Rulcova A.Prokopova I.Krausova L.Bitman M.Vrzal R.Dvorak Z.Blahos J.Pavek P. J. Thromb. Haemost. 2010, 8: 2708 - 6d 
             
            
Remkova A.Milatova E.Fuchsbergerova M. Blood Coagulation Fibrinolysis 2010, 21: 487 - 6e 
             
            
Di Bari L.Ripoli S.Pradhan S.Salvadori P. Chirality 2010, 22: 593 - 7a 
             
            
Nazari ZE.Iranshahi M. Phytother. Res. 2011, 25: 315 - 7b 
             
            
Hwu JR.Lin S.-Y.Tsay S.-C.De Clercq E.Leyssen P.Neyts J. J. Med. Chem. 2011, 54: 2114 - 7c 
             
            
Mazzei M.Nieddu E.Miele M.Balbi A.Ferrone M.Fermeglia M.Mazzei MT.Pricl S.La Colla P.Marongiu F.Ibba C.Loddo R. Bioorg. Med. Chem. 2008, 16: 2591 - 7d 
             
            
Randhavane P.Karale B. J. Heterocycl. Chem. 2009, 46: 732 - 7e 
             
            
Giampieri M.Balbi A.Mazzei M.La Colla P.Ibba C.Loddo R. Antiviral Res. 2009, 83: 179 - 7f 
             
            
Spino C.Dodier M.Sotheeswaran S. Bioorg. Med. Chem. Lett. 1998, 8: 3475 - 8a 
             
            
Riveiro ME.Moglioni A.Vazquez R.Natalia G.Facorro G.Piehl L.de Celis ER.Shayod C.Davio C. Bioorg. Med. Chem. 2008, 16: 2665 - 8b 
             
            
Riveiro ME.Vazquez R.Moglioni A.Gomez N.Baldi A.Davio C.Shayo C. Biochem. Pharmacol. 2008, 75: 725 - 8c 
             
            
Gao Z.Maloney DJ.Dedkova LM.Hecht SM. Bioorg. Med. Chem. 2008, 16: 4331 - 8d 
             
            
Win NN.Awale S.Esumi H.Tezuka Y.Kadota S. Bioorg. Med. Chem. 2008, 16: 8653 - 8e 
             
            
Radanyi C.Le Bras G.Messaoudi S.Bouclier C.Peyrat J.-F.Brion J.-D.Marsaud V.Renoirb J.-M.Alami M. Bioorg. Med. Chem. Lett. 2008, 18: 2495 - 8f 
             
            
Fong W.-F.Shen X.-L.Globisch C.Wiese M.Chen G.-Y.Zhu G.-Y.Yu Z.-L.Tsea AK.-W.Hu Y.-J. Bioorg. Med. Chem. 2008, 16: 3694 - 8g 
             
            
Han H.-Y.Wen P.Liu H.-W.Wang N.-L.Yao X.-S. Chem. Pharm. Bull. 2008, 56: 1338 - 8h 
             
            
Beillerot A.Domínguez J.-CR.Kirsch G.Bagrel D. Bioorg. Med. Chem. Lett. 2008, 18: 1102 - 8i 
             
            
Kostova I.Momekov G. Eur. J. Med. Chem. 2008, 43: 178 - 9 
             
            
Pechmann HV.Duisberg C. Ber. Dtsch. Chem. Ges. 1883, 16: 22119 - 10a 
             
            
Bose DS.Rudradas AP.Babu MH. Tetrahedron Lett. 2002, 43: 9195 - 10b 
             
            
Nam N.-H.Kim Y.You Y.-J.Hong D.-H.Kimb H.-M.Ahn B.-Z. Bioorg. Med. Chem. Lett. 2002, 12: 2345 - 10c 
             
            
Rodríguez-Domíngues JC.Kirsch G. Tetrahedron Lett. 2006, 47: 3279 - 11a 
             
            
Shanmuganathan S.Greiner L.de María PD. Tetrahedron Lett. 2010, 51: 6670 - 11b 
             
            
Shea KJ.Loy DA. Chem. Mater. 2001, 13: 3306 - 12a 
             
            
Dong F.Jian C.Kai G.Qunrong S.Zuliang L. Catal. Lett. 2008, 121: 255 - 12b 
             
            
Potdar MK.Rasalkar MS.Mohile SS.Salunkhe MM. J. Mol. Catal. A: Chem. 2005, 235: 249 - 12c 
             
            
Sabou R.Hoelderich WF.Ramprasad D.Weinand R. J. Catal. 2005, 232: 34 - 13 
             
            
Manhas MS.Ganguly SN.Mukherjee S.Jain AK.Bose AK. Tetrahedron Lett. 2006, 47: 2423 - 14a 
             
            
Yadav LDS.Singh S.Rai VK. Tetrahedron Lett. 2009, 50: 2208 - 14b 
             
            
Bull JA.Luján C.Hutchings MG.Guayle P. Tetrahedron Lett. 2009, 50: 3617 - 15 
             
            
Potdar MK.Mohile SS.Salunkhe MM. Tetrahedron Lett. 2001, 42: 9285 - 16a 
             
            
Maes D.Eugenia MR.Shayo C.Davio C.Debenedetti S.De Kimpe N. Tetrahedron 2008, 64: 4438 - 16b 
             
            
Upadhyay PK.Kumar P. Tetrahedron Lett. 2009, 50: 236 - 17a 
             
            
Fernandes T. de A.Vaz BG.Eberlin MN.da Silva AJM.Costa PRR. J. Org. Chem. 2010, 75: 7085 - 17b 
             
            
Battistuzzi G.Cacchi S.De Salve I.Fabrizi G.Parisi LM. Adv. Synth. Catal. 2005, 347: 308 - 17c 
             
            
Ulgheri F.Marchetti M.Piccolo O. J. Org. Chem. 2007, 72: 605 - 17d 
             
            
Fernandes T. de A.Carvalho RCC.Gonçalves TMD.da Silva AJM.Costa PRR. Tetrahedron Lett. 2008, 49: 3322 - 17e 
             
            
Giguere D.Patnam R.Juarez-Ruiz JM.Neault M.Roy R. Tetrahedron Lett. 2009, 50: 4254 - 17f 
             
            
Kadnikov DV.Larock RC. Org. Lett. 2000, 2: 3643 - 18a 
             
            
Trost BM.Toste FD.Greenman K. J. Am. Chem. Soc. 2003, 125: 4518 - 18b 
             
            
Trost BM.Toste FD. J. Am. Chem. Soc. 1996, 118: 6305 - 18c 
             
            
Kitamura T.Oyamada J.Tsubota T. Nat. Protoc. 2007, 2: 845 - 18d 
             
            
Kotani M.Yamamoto K.Oyamada J.Fujiwara Y.Kitamura T. Synthesis 2004, 1466 - 19a 
             
            
Shi Z.He C. J. Org. Chem. 2004, 69: 3669 - 19b 
             
            
Menon RS.Findlay AD.Bissember AC.Banwell MG. J. Org. Chem. 2009, 74: 8901 - 20 
             
            
Oyamada J.Kitamura T. Tetrahedron 2006, 62: 6918 - 21 
             
            
Yamamoto Y.Kirai N. Org. Lett. 2008, 10: 5513 - 22a 
             
            
Kaufman KD.Kelly RC. Heterocycl. Chem. 1965, 2: 91 - 22b 
             
            
Chang C.-F.Yang L.-Y.Chang S.-W.Fang Y.-T.Lee Y.-J. Tetrahedron 2008, 64: 3661 - 23a 
             
            
Iqbal PF.Bhat AR.Azam A. Eur. J. Med. Chem. 2009, 44: 2252 - 23b 
             
            
Sethna SM.Shah NM. Chem. Rev. 1945, 36: 1 - 23c 
             
            
Bridge W.Crocker AJ.Cubin T.Robertson A. J. Chem. Soc. 1937, 140: 1530 - 24a 
             
            
Haig TJ.Haig TJ.Seal AN.Pratley JE.An M.Wu H. J. Chem. Ecol. 2009, 35: 1129 - 24b 
             
            
Smyth WF.Ramachandran VN.Hack CJ.Joyce C.O’Kane E. Anal. Chim. Acta 2006, 564: 201 - 24c 
             
            
Jivaramonaikul W.Rashatasakhon P.Wanichwecharungruang S. Photochem. Photobiol. Sci. 2010, 9: 1120 - 25 
             
            
Ismail S.Hanapi NA.Ab Halim MR.Uchaipichat V.Mackenzie PI. Molecules 2010, 15: 3578 - 26a 
             
            
Brenzan MA.Nakamura CV.Filho BPD.Ueda-Nakamura T.Young MCM.Côrrea AG.Júnior JA.dos Santos AO.Cortez DAG. Biomed. Pharmacother. 2008, 62: 651 - 26b 
             
            
Bennardi DO.Ruiz DM.Romanelli GP.Baronetti GT.Thomas HJ.Autino JC. Lett. Org. Chem. 2008, 5: 607 - 27a 
             
            
Raad I.Terreux R.Richomme P.Matera E.-L.Dumontet C.Raynauda J.Guileta D. Bioorg. Med. Chem. 2006, 14: 6979 - 27b 
             
            
Sun J.Ding WX.Zhang KY.Zou Y. Chin. Chem. Lett. 2011, 22: 667 - 28 
             
            
Vogl S.Zehl M.Picker P.Urban E.Wawrosch C.Reznicek G.Saukel J.Kopp B. J. Agric. Food Chem. 2011, 59: 4371 - 29a 
             
            
Maes D.Vervisch S.Debenedetti S.Davio C.Mangelinckx S.Giubellina N.De Kimpe N. Tetrahedron 2005, 61: 2505 - 29b 
             
            
Mors WB.do Nascimento MC.Pereira BMR.Pereira NA. Phytochemistry 2000, 55: 627