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Synthesis 2010(24): 4256-4260
DOI: 10.1055/s-0030-1258312
DOI: 10.1055/s-0030-1258312
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkCopper(I) Iodide-Catalyzed Synthesis of 4-Aryl-1H-1,2,3-triazoles from anti-3-Aryl-2,3-dibromopropanoic Acids and Sodium Azide
Further Information
Received
27 August 2010
Publication Date:
22 October 2010 (online)
Publication History
Publication Date:
22 October 2010 (online)

Abstract
4-Aryl-1H-1,2,3-triazoles were synthesized from anti-3-aryl-2,3-dibromopropanoic acids and sodium azide by using inexpensive copper(I) iodide as the catalyst in dimethyl sulfoxide.
Key words
cyclizations - catalysis - heterocycles - azides - triazoles
- 1a
Rostovtsev VV.Green LG.Fokin VV.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596 - 1b
Kolb HC.Finn MG.Sharpless KB. Angew. Chem. Int. Ed. 2001, 40: 2004 - 1c
Moses JE.Moorhouse AD. Chem. Soc. Rev. 2007, 36: 1249 - 1d
Wu P.Fokin VV. Aldrichimica Acta 2007, 40: 7 - 2a
Chabre YM.Roy R. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 2008, 8: 1237 - 2b
Colombo M.Peretto I. Drug Discovery Today 2008, 13: 677 - 2c
Hanselmann R.Job GE.Johnson G.Lou RL.Martynow JG.Reeve MM. Org. Process Res. Dev. 2010, 14: 152 - 2d
Moumne R.Larue V.Seijo B.Lecourt T.Micouin L.Tisne C. Org. Biomol. Chem. 2010, 8: 1154 - 3a
Li HM.Cheng FO.Duft AM.Adronov A. J. Am. Chem. Soc. 2005, 127: 14518 - 3b
Rozkiewicz DI.Jańczewski D.Verboom W.Ravoo BJ.Reinhoudt DN. Angew. Chem. Int. Ed. 2006, ; 45: 5292 - 3c
Wyszogrodzka M.Haag R. Chem. Eur. J. 2008, 14: 9202 - 3d
Gadzikwa T.Farha OK.Malliakas CD.Kanatzidis MG.Hupp JT.Nguyen S.-BT. J. Am. Chem. Soc. 2009, 131: 13613 - 3e
Golas PL.Matyjaszewski K. Chem. Soc. Rev. 2010, 39: 1338 - 3f
Bronisz R. Inorg. Chem. 2005, 44: 4463 - 3g
Yue YF.Wang BW.Gao EQ.Fang CJ.He C.Yan CH. Chem. Commun. 2007, 2034 - 3h
Fazio MA.Lee OP.Schuster DI. Org. Lett. 2008, 10: 4979 - 3i
Fletcher JT.Bumgarner BJ.Engels ND.Skoglund DA. Organometallics 2008, 27: 5430 - 3j
Hua YR.Flood AH. Chem. Soc. Rev. 2010, 39: 1262 - 3k
Rawal GK.Zhang P.Ling C. Org. Lett. 2010, 12: 3096 - 4a
Hahn ME.Muir TW. Trends Biochem. Sci. 2005, 30: 26 - 4b
Heal WP.Wickramasinghe SR.Leatherbarrow RJ.Tate EW. Org. Biomol. Chem. 2008, 6: 2308 - 4c
Ahsanullah MP.Schmieder P.Kuhne R.Rademann J. Angew. Chem. Int. Ed. 2009, 48: 5042 - 4d
Schneider G. Nat. Rev. Drug Discovery 2010, 9: 273 - 4e
Chemama M.Fonvielle M.Arthur M.Valéry JM.Etheve-Quelquejeu M. Chem. Eur. J. 2009, 15: 1929 - 4f
Nahrwold M.Bogner T.Eissler S.Verma S.Sewald N. Org. Lett. 2010, 12: 1064 - 4g
Michaels HA.Murphy CS.Clark RJ.Davidson MW.Zhu L. Inorg. Chem. 2010, 49: 4278 - 4h
Mamidyala SK.Finn MG. Chem. Soc. Rev. 2010, 39: 1252 - 5
Genin MJ.Allwine DA.Anderson DJ.Barbachyn MR.Emmert DE.Garmon SA.Graber DR.Grega KC.Hester JB.Hutchinson DK.Morris J.Reischer RD.Ford CW.Zurenko GE.Hamel JC.Schaadt RD.Stapert D.Yagi BH. J. Med. Chem. 2000, 43: 953 - 6
Wamhoff H. In Comprehensive Heterocyclic Chemistry Vol. 5:Katritzky AR.Rees CW. Pergamon; Oxford: 1984. p.669-732 - 7
Buckle DR.Rockell CJM.Smith H.Spicer BA. J. Med. Chem. 1986, 29: 2262 - 8
Alvarez R.Velazquez S.San-Felix A.Aquaro S.De Clercq E.Perno CF.Karlsson A.Balzarini J.Camarasa MJ. J. Med. Chem. 1994, 37: 4185 - 9a
Chan TR.Hilgraf R.Sharpless KB.Fokin VV. Org. Lett. 2004, 6: 2853 - 9b
Liu D.Gao WZ.Dai Q.Zhang XM. Org. Lett. 2005, 7: 4907 - 9c
Detz RJ.Heras SA.de Gelder R.van Leeuwen P.Hiemstra H.Reek JNH.van Maarseveen JH. Org. Lett. 2006, 8: 3227 - 9d
Colasson B.Save M.Milko P.Roithova J.Schroder D.Reinaud O. Org. Lett. 2007, 9: 4987 - 9e
Beyer B.Ulbricht C.Escudero D.Friebe C.Winter A.González L.Schubert US. Organometallics 2009, 28: 5478 - 9f
Hein JE.Tripp JC.Krasnova LB.Sharpless KB.Fokin VV. Angew. Chem. Int. Ed. 2009, 48: 8018 - 9g
Duan H.Sengupta S.Petersen JL.Akhmedov NG.Shi X. J. Am. Chem. Soc. 2009, 131: 12100 - 9h
Duan H.Sengupta S.Petersen JL.Shi X. Organometallics 2009, 28: 2352 - 9i
Mager I.Zeiler K. Org. Lett. 2010, 12: 1480 - 10a
Meldal M.Tornøe CW. Chem. Rev. 2008, 108: 2952 - 10b
Bock VD.Hiemstra H.van Maarseveen JH. Eur. J. Org. Chem. 2006, 51 - 10c
Nandivada H.Jiang X.Lahann J. Adv. Mater. (Weinheim, Ger.) 2007, 19: 2197 - 10d
Tron GC.Pirali T.Billington RA.Canonico PL.Sorba G.Genazzani AA. Med. Res. Rev. 2008, 28: 278 - 10e
Becer CR.Hoogenboom R.Schubert US. Angew. Chem. Int. Ed. 2009, 48: 4900 - 10f
Spiteri C.Moses JE. Angew. Chem. Int. Ed. 2010, 49: 31 - 10g
Kolb HC.Finn MG.Sharpless KB. Angew. Chem. Int. Ed. 2001, 40: 2004 - 10h
Lutz J.-F. Angew. Chem. Int. Ed. 2007, 46: 1018 - 10i
Fukuzawa S.Shimizu E.Kikuchi S. Synlett 2007, 2436 - 10j
Aucagne V.Berna J.Crowley JD.Goldup SM.Hanni KD.Leigh DA.Lusby PJ.Ronaldson VE.Slawin AMZ.Viterisi A.Walker DB. J. Am. Chem. Soc. 2007, 129: 11950 - 10k
Wu LY.Xie YX.Chen ZS.Liu YN.Liang YM. Synlett 2009, 1453 - 10l
Yan ZY.Wei HL.Wu LY.Zhao YB.Liang YM. Tetrahedron: Asymmetry 2006, 17: 3288 - 10m
Yan ZY.Zhao YB.Fan MJ.Liu WM.Liang YM. Tetrahedron 2005, 61: 9331 - 10n
Cristau HJ.Cellier PP.Spindler JF.Taillefer M. Chem. Eur. J. 2004, 10: 5607 - 10o
Chen Z.Zhu J.Xie H.Li S.Wu Y. Adv. Synth. Catal. 2010, 352: 1296 - 10p
Chattppadhyay B.Rivera Vera CI.Chuprakov S.Gevorygan V. Org. Lett. 2010, 12: 2166 - 10q
Fletcher JT.Walz SE.Keeney ME. Tetrahedron Lett. 2008, 49: 7030 - 10r
Yan Ji.Wang L. Synthesis 2010, 447 - 10s
Li P.Wang L.Zhang Y. Tetrahedron 2008, 64: 10825 - 10t
Li P.Wang L. Lett. Org. Chem. 2007, 4: 23 - 11a
Jin T.Kamijo S.Yamamoto Y. Eur. J. Org. Chem. 2004, 3789 - 11b
Kamijo S.Huo Z.Jin T.Kanazawa C.Yamamoto Y. J. Org. Chem. 2005, 70: 6389 - 11c
Loren JC.Krasiński A.Fokin VV.Sharpless KB. Synlett 2005, 2847 - 12a
Katritzky AR.Zhang Y.Singh SK. Heterocycles 2003, 60: 1225 - 12b
Journet M.Cai D.Kowal JJ.Larsen RD. Tetrahedron Lett. 2001, 42: 9117 - 13a
Zefirov NS.Chapovskaya NK.Kolesnikov VV.
J. Chem. Soc. D 1971, 1001 - 13b
Quiclet-Sire B.Zard SZ. Synthesis 2005, 3319 - 14a
Banert K. Chem. Ber. 1989, 122: 911 - 14b
Banert K. Chem. Ber. 1989, 122: 1175 - 14c
Banert K. Chem. Ber. 1989, 122: 1963 - 14d
Banert K.Hagedorn M. Angew. Chem. Int. Ed. 1989, 28: 1675 - 14e
Loren JC.Sharpless KB. Synthesis 2005, 1514 - 15
Barluenga J.Valdés C.Beltrén G.Escribano M.Aznar F. Angew. Chem. Int. Ed. 2006, 45: 6893 - 16
Zhang W.Kuang C.Yang Q. Synthesis 2010, 283 - 17a
Kuang C.Senboku H.Tokuda M. Tetrahedron Lett. 2001, 42: 3893 - 17b
Zhang W.Kuang C.Yang Q. Chin. J. Chem. 2009, 27: 1727 - 18
Kalland er LS, andThompson SK. inventors; WO 0178723. - 19
Kallander LS.Lu Q.Chen W.Tomaszek T.Yang G.Tew D.Meek TD.Hofmann GA. J. Med. Chem. 2005, 48: 5644 - 20
Kalisiak J.Sharpless KB.Fokin VV. Org. Lett. 2008, 10: 3171