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 2009(8): 1341-1347
DOI: 10.1055/s-0028-1088017
DOI: 10.1055/s-0028-1088017
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Novel 1,4-Benzoquinone-Containing 1,2,3-Triazoles: An Entry Into a New Library
Further Information
Received
24 November 2008
Publication Date:
16 March 2009 (online)
Publication History
Publication Date:
16 March 2009 (online)
Abstract
A heretofore unexplored library of 1,4-benzoquinone-containing 1,2,3-triazoles was prepared by the application of a highly regioselective copper(I)-catalyzed process. Furthermore, the utilization of this novel triazole-1,4-benzoquinone system as an interesting class of extended, branched molecules for the construction of new supramolecular architectures is presented.
Key words
benzoquinones - azides - triazoles - copper(I) catalysis - regioselectivity
-
1a
Dehne H. In Houben-Weyl Vol. E8d:Schumann E. Thieme; Stuttgart: 1994. p.305-405 -
1b
Wamhoff H. In Comprehensive Heterocyclic Chemistry Vol. 5:Katritzky AR.Rees CW. Pergamon; Oxford: 1984. p.669-732 - For triazole activity studies, see:
-
2a
Alvarez R.Velazquez S.San F.Aquaro S.De C.Perno CF.Karlesson A.Balzarini J.Camarasa MJ. J. Med. Chem. 1994, 37: 4185 -
2b
Genin MJ.Allwine DA.Anderson DJ.Barbachyne MR.Emmert DE.Garmon SA.Graber DR.Grega KC.Hester JB.Hutchinson DK.Morris J.Reischer RJ.Ford CW.Zurence GE.Hamel JC.Schaadt RD.Stapertand D.Yagi BH. J. Med. Chem. 2000, 43: 953 -
2c
Brockunier LL.Parmee ER.Ok HO.Candelore MR.Casciere MA.Colwell LF.Deng L.Feeney WP.Forest MJ.Hom GJ.MacIntyre DE.Tota L.Wyvratt MJ.Fisher MH.Weber AE. Bioorg. Med. Chem. Lett. 2000, 10: 2111 -
3a For
recent reviews on organic azides, see:
Brase S.Gil C.Knepper K.Zimmermann V. Angew. Chem. Int. Ed. 2005, 44: 5188 -
3b
Sha C.Mohanakrishnan AK. In The Chemistry of Heterocyclic Compounds Vol. 59:Padwa A.Pearson WH. John Wiley & Sons; Hoboken: 2002. p.623-679 - For the synthesis and/or applications of 1,5-triazoles, see:
-
4a
Krasinski A.Fokin VV.Sharpless KB. Org. Lett. 2004, 6: 1237 -
4b
Zhang L.Chen X.Xue P.Sun HHY.Williams ID.Sharpless KB.Fokin VV.Jia G. J. Am. Chem. Soc. 2005, 127: 15998 -
4c
Liu D.Gao W.Dai Q.Zhang X. Org. Lett. 2005, 7: 4907 -
5a
Garanti L.Molteni G. Tetrahedron Lett. 2003, 44: 1133 -
5b
Katritzky AR.Singh SK. J. Org. Chem. 2002, 67: 9077 -
5c
Suzuki H.Nakaya C.Matano Y. Tetrahedron Lett. 1993, 34: 1055 - On copper-catalyzed synthesis and/or applications of 1,2,3-triazoles, see:
-
6a
Rostovtsev VV.Green LG.Fokin VV.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596 -
6b
Tornoe CW.Christensen C.Medal M. J. Org. Chem. 2002, 67: 3057 -
6c
Jin T.Kamijo S.Yamamoto Y. Eur. J. Org. Chem. 2004, 3789 -
6d
Fazio F.Bryan MC.Blixt O.Paulson JC.Wong CH. J. Am. Chem. Soc. 2002, 124: 14397 -
6e
Wang Q.Chan RC.Hilgraf R.Fokin VV.Sharpless KB.Finn MG. J. Am. Chem. Soc. 2003, 125: 3192 -
6f
Löber S.Rodriguez-Loaiza P.Gmeiner P. Org. Lett. 2003, 5: 1753 -
6g
Perez-Balderas F.Ortega-Munoz M.Morales-Sanfrutos J.Hernandez-Mateo F.Calvo-Flores FG.Calvo-Asin JA.Isac-Garcia J.Santoyo-Gonzales F. Org. Lett. 2003, 5: 1951 -
6h
Rodinov VO.Fokin VV.Finn MG. Angew. Chem. Int. Ed. 2005, 44: 2210 - 7
Balci M.Çelik M.Gültekin MS. In Science of Synthesis Vol. 28:Griesbeck AG. Thieme; Stuttgart: 2006. p.31-180 - 8
O’Malley PJ. Chem. Phys. Lett. 1997, 274: 251 - 9
Blanchard JS.Marcinkeviciene JA. Biochemistry 1995, 34: 6621 ; and references cited therein - For structure-activity studies of 1,4-benzoquinones, see:
-
10a
Sami SM.Iyengar BS.Tarnow SE.Remers WA.Bradner WT.Schurig JE. J. Med. Chem. 1984, 27: 701 -
10b
Shaikh IA.Johnson F.Grollman AP. J. Med. Chem. 1986, 29: 1329 -
10c
Kunz KR.Iyengar BS.Dorr RT.Alberts DS.Remers WA. J. Med. Chem. 1991, 34: 2281 -
10d
Arai H.Ashizawa T.Gomi K.Kono M.Saito H.Kasai M. J. Med. Chem. 1995, 38: 3025 -
10e
Hernick M.Flader C.Borch RF. J. Med. Chem. 2002, 45: 3540 -
11a
Martinez-Manez R.Sancenon F. Chem. Rev. 2003, 103: 4419 -
11b
Callan JF.de Silva AP.Magri DC. Tetrahedron 2005, 61: 8551 - 12
Algi F.Balci M. Synth. Commun. 2006, 36: 2293 - 13
Halper SR.Cohen SM. Chem. Eur. J. 2003, 9: 4661 ; and references cited therein - 14
Clark CO.Poole CP.Farach HA. J. Phys. C: Solid State Phys. 1978, 11: 769