Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(2): 283-287
DOI: 10.1055/s-0029-1217097
DOI: 10.1055/s-0029-1217097
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium-Catalyzed One-Pot Synthesis of 4-Aryl-1H-1,2,3-triazoles from anti-3-Aryl-2,3-dibromopropanoic Acids and Sodium Azide
Further Information
Received
24 August 2009
Publication Date:
03 November 2009 (online)
Publication History
Publication Date:
03 November 2009 (online)
Abstract
4-Aryl-1H-1,2,3-triazoles were synthesized from anti-3-aryl-2,3-dibromopropanoic acids and sodium azide by a one-pot method using N,N-dimethylformamide as solvent in the presence of tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3] and Xantphos.
Key words
1H-1,2,3-triazole - anti-3-aryl-2,3-dibromopropanoic acid - sodium azide - Pd2(dba)3 - one-pot
- 1
Katritzky AR.Zhang Y.Singh SK. Heterocycles 2003, 60: 1225 -
2a
Tornøe CW.Christensen C.Meldal M. J. Org. Chem. 2002, 67: 3057 -
2b
Rostovtsev VV.Green LG.Fokin VV.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596 - 3
Kolb HC.Sharpless KB. Drug Discovery Today 2003, 8: 1128 ; and references cited therein -
4a
Wu P.Feldman AK.Nugent AK.Hawker CJ.Scheel A.Voit B.Pyun J.Frechet JMJ.Sharpless KB.Fokin VV. Angew. Chem. Int. Ed. 2004, 43: 3928 -
4b
Helms B.Mynar JL.Hawker CJ.Frechet JMJ. J. Am. Chem. Soc. 2004, 126: 15020 -
4c
Scheel A.Komber H.Voit B. Macromol. Rapid Commun. 2004, 25: 1175 -
4d
Parent M.Mongin O.Kamada K.Katan C.Blanchard-Desce M. Chem. Commun. 2005, 2029 -
4e
van Steenis DJVC.David ORP.van Strijdonck GPF.van Maarseveen JH.Reek JNH. Chem. Commun. 2005, 4333 -
5a
Löber S.Rodriguez-Loaiza P.Gmeiner P. Org. Lett. 2003, 5: 1753 -
5b
Harju K.Vahermo M.Mutikainen I.Yli-Kauhaluoma J. J. Comb. Chem. 2003, 5: 826 -
5c
Khanetskyy B.Dallinger D.Kappe CO. J. Comb. Chem. 2004, 6: 884 -
5d
Tornoe CW.Sanderson SJ.Mottram JC.Coombs GH.Meldal M. J. Comb. Chem. 2004, 6: 312 - 6
Genin MJ.Allwine DA.Anderson DJ.Barbachyn MR.Emmert DE.Garmon SA.Graber DR.Grega KC.Hester JB.Hutchinson DK.Morris J.Reischer RD.Stper D.Yagi BH. J. Med. Chem. 2000, 43: 953 - 7
Wamhoff H. In Comprehensive Heterocyclic ChemistryKatritzky AR.Rees CW. Pergamon; Oxford: 1984. p.669-732 - 8
Buckle DR.Rockell CJM.Smith H.Spicer BA. J. Med. Chem. 1986, 29: 2262 - 9
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: 4194 - 10
Kolb HC.Finn MG.Sharpless KB. Angew. Chem. Int. Ed. 2001, 40: 2004 - 11
Bock VD.Hiemstra H.van Maarseveen JH. Eur. J. Org. Chem. 2006, 51 -
12a
Kallander LS.Lu Q.Chen W.Tomaszek T.Yang G.Tew D.Meek TD.Hofmann GA.Schulz-Pritchard CK.Smith WW.Janson CC.Ryan MD.Zhang G.-F.Johanson KO.Kirkpatrick RB.Ho TF.Fisher PW.Mattern MR.Johnson RK.Hansbury MJ.Winkler JD.Ward KW.Veber DF.Thompson SK. J. Med. Chem. 2005, 48: 5644 -
12b
Amantini D.Fringuelli F.Piermatti O.Pizzo F.Zunino E.Vaccaro L. J. Org. Chem. 2005, 70: 6526 ; and references cited therein -
13a
Jin T.Kamijo S.Yamamoto Y. Eur. J. Org. Chem. 2004, 3789 -
13b
Kamijo S.Huo Z.Jin T.Kanazawa C.Yamamoto Y. J. Org. Chem. 2005, 70: 6389 -
13c
Loren JC.Krasiński A.Fokin VV.Sharpless KB. Synlett 2005, 2847 - 14
Journet M.Cai D.Kowal JJ.Larsen RD. Tetrahedron Lett. 2001, 42: 9117 -
15a
Zefirov NS.Chapovskaya NK.Kolesnikov VV. J. Chem. Soc. D 1971, 1001 -
15b
Quiclet-Sire B.Zard SZ. Synthesis 2005, 3319 -
16a
Banert K. Chem. Ber. 1989, 122: 911 -
16b
Banert K. Chem. Ber. 1989, 122: 1175 -
16c
Banert K. Chem. Ber. 1989, 122: 1963 -
16d
Banert K.Hagedorn M. Angew. Chem., Int. Ed. Engl. 1989, 28: 1675 -
16e
Loren JC.Sharpless KB. Synthesis 2005, 1514 - 17
Barluenga J.Valdés C.Beltrén G.Escribano M.Aznar F. Angew. Chem. Int. Ed. 2006, 45: 6893 -
18a
Grovenstein JE.Lee DE. J. Am. Chem. Soc. 1953, 75: 2639 -
18b
Cristol SJ.Norris WP. J. Am. Chem. Soc. 1953, 75: 2645 -
18c
Paquette LA.Fristad WE.Dime DS.Bailey TR. J. Org. Chem. 1980, 45: 3017 -
18d
Galamb V.Alper H. Tetrahedron Lett. 1983, 24: 2965 -
18e
Murahashi S.Naota T.Tanigawa Y. Org. Synth. 1984, 62: 39 -
18f
Fuller CE.Walker DG. J. Org. Chem. 1991, 56: 4066 -
18g
Mori K.Brevet J.-L. Synthesis 1991, 1125 -
18h
Pinhey JT.Stoermer MJ. J. Chem. Soc., Perkin Trans. 1 1991, 2455 -
18i
Brevet JL.Mori K. Synthesis 1992, 1007 -
18j
Matveeva ED.Erin AS.Kurz AL. Russ. J. Org. Chem. 1997, 33: 1065 -
18k
Kim SH.Wei HX.Willis S.Li G. Synth. Commun. 1999, 29: 4179 -
18l
Yasuike S.Shiratori S.Kurita J.Tsuchiya T. Chem. Pharm. Bull. 1999, 47: 1108 -
18m
Kuang C.Senboku H.Tokuda M. Tetrahedron Lett. 2001, 42: 3893 -
18n
Ponte GD.Arcanjo FC.Botteghi C. J. Mol. Catal. A: Chem. 2003, 192: 35 -
18o
Kuang C.Senboku H.Tokuda M. Tetrahedron 2005, 61: 637 -
18p
Zhang W.Kuang C.Yang Q. Chin. J. Chem. 2009, 27: 1727 - 19
Kalisiak J.Sharpless KB.Fokin VV. Org. Lett. 2008, 10: 3171 - 20
Ito S.Kakehi A.Yamazaki A. Chem. Lett. 1990, 3: 453 - 21
Jin T.Kamijo S.Yamamoto Y. Eur. J. Org. Chem. 2004, 3789 - 22
Li W.Xia Y.Fan Z.Qu F.Wu Q.Peng L. Tetrahedron Lett. 2008, 49: 2804 - 23
Subbaraman R.Ghassemi H.Zawodzinski T. Preprints of Symposia - ACS Division of Fuel Chemistry Vol. 51: American Chemical Society; Washington DC: 2006. p.684