RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(4): 551-554
DOI: 10.1055/s-2008-1032018
DOI: 10.1055/s-2008-1032018
PAPER
© Georg Thieme Verlag Stuttgart · New YorkAn Efficient Three-Component Reaction Involving Triazolylidene Carbene, DMAD, and Aldehydes for the Synthesis of Furanone Derivatives
Weitere Informationen
Received
14 November 2007
Publikationsdatum:
10. Januar 2008 (online)
Publikationsverlauf
Publikationsdatum:
10. Januar 2008 (online)

Abstract
An efficient synthesis of furanone derivatives via the multicomponent reaction involving triazolylidene carbene, dimethyl acetylenedicarboxylates, and aldehydes is described.
Key words
zwitterion - triazolylidene carbene - DMAD - furanone - multicomponent reactions
- For reviews, see:
- 1a
Enders D.Balensiefer T. Acc. Chem. Res. 2004, 37: 534 - 1b
Nair V.Bindu S.Sreekumar V. Angew. Chem. Int. Ed. 2004, 43: 5130 - 1c
Cheng Y.Meth-Cohn O. Chem. Rev. 2004, 104: 2507 - 1d
Zeitler K. Angew. Chem. Int. Ed. 2005, 44: 7506 - 1e
Marion N.Diez-Gonzalez S.Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988 - 2
Breslow R. J. Am. Chem. Soc. 1958, 80: 3719 - 3
Wanzlick H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1: 75 - 4
Arduengo AJ.Harlow RL.Kline MK. J. Am. Chem. Soc. 1991, 113: 361 - 5a
Enders D.Niemeier O.Balensiefer T. Angew. Chem. Int. Ed. 2006, 45: 1463 - 5b
Hachisu Y.Bode JW.Suzuki K. J. Am. Chem. Soc. 2003, 125: 8432 - 6a
Grasa GA.Kissling RM.Nolan SP. Org. Lett. 2002, 4: 3583 - 6b
Grasa GA.Güveli T.Singh R.Nolan SP. J. Org. Chem. 2003, 68: 2812 - 6c
Nyce GW.Lamboy JA.Connor EF.Waymouth JL.Hedrick RM. Org. Lett. 2002, 4: 3587 - 6d
Singh R.Kissling RM.Letellier M.-A.Nolan SP. J. Org. Chem. 2004, 69: 209 - 7a
Teles JH.Melder JP.Ebel K.Schneider GE.Harder W.Brode S.Enders D.Breuer K.Rabbe G. Helv. Chim. Acta 1996, 79: 1271 - 7b
Davis JH.Forrester K. Tetrahedron Lett. 1999, 40: 1621 - 7c
Enders D.Breuer K.Runsink J.Teles JH. Helv. Chim. Acta 1996, 79: 1899 - 8a
Regitz M. Angew. Chem., Int. Ed. Engl. 1996, 35: 725 - 8b
Bourissou D.Guerret O.Gabbai FP.Betrand G. Chem. Rev. 2000, 100: 39 - 9a
Sohn SS.Rosen EL.Bode JW. J. Am. Chem. Soc. 2004, 126: 14370 - 9b
Burstein C.Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205 - 9c
Nair V.Vellalath S.Poonoth M.Suresh E. J. Am. Chem. Soc. 2006, 128: 8736 - 9d
Christmann M. Angew. Chem. Int. Ed. 2005, 44: 2632 - 10a
Nair V.Bindu S.Sreekumar V.Rath NP. Org. Lett. 2003, 5: 665 - 10b
Nair V.Sreekumar V.Bindu S.Suresh E. Org. Lett. 2005, 7: 2299 - 11a
Ma C.Yang Y. Org. Lett. 2005, 7: 1343 - 11b
Ma C.Ding H.Zhang Y.Bian M. Angew. Chem. Int. Ed. 2006, 45: 1 - 12a
Enders D.Breuer K.Rabbe G.Runsink J.Teles JH.Melder J.-P.Ebel K.Brode S. Angew. Chem. Int. Ed. 1995, 34: 1021 - 12b
Enders D.Breuer K.Rabbe G.Runsink J.Teles JH. Liebigs Ann. Chem. 1996, 2019 - 12c
Enders D.Breuer K.Kallfass U.Balensiefer T. Synthesis 2003, 1292 - 13
Knight RL.Leeper F. J. Chem. Soc., Perkin Trans. 1 1998, 1891 - 14
Enders D.Kallfass U. Angew. Chem. Int. Ed. 2002, 41: 1743 - 15a
Kerr MS.Read de Alainz J.Rovis T. J. Am. Chem. Soc. 2002, 124: 10298 - 15b
Kerr MS.Rovis T. Synlett 2003, 1934 - 15c
Pesch J.Harms K.Bach T. Eur. J. Org. Chem. 2004, 2025 - 16a
Nair V.Rajesh C.Vinod AU.Bindu S.Sreekanth AR.Mathen JS.Balagopal L. Acc. Chem. Res. 2003, 36: 899 - 16b
Pillai AN.Devi BR.Suresh E.Nair V. Tetrahedron Lett. 2007, 48: 4391
References
CCDC file 656836 contains the supplementary crystallographic data for compound 4a. The data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/products/csd/request.