An Efficient Three-Component Reaction Involving Triazolylidene Carbene, DMAD, and Aldehydes for the Synthesis of Furanone Derivatives

Vijay Nair; Smitha C. Mathew; Sreekumar Vellalath; Abhilash N. Pillai; Eringathodi Suresh

doi:10.1055/s-2008-1032018

PAPER

An Efficient Three-Component Reaction Involving Triazolylidene Carbene, DMAD, and Aldehydes for the Synthesis of Furanone Derivatives

Vijay Nair*^a, Smitha C. Mathew^a, Sreekumar Vellalath^a, Abhilash N. Pillai^a, Eringathodi Suresh^b
^a Organic Chemistry Section, National Institute for Interdisciplinary Science and Technology (Formerly RRL-Trivandrum)-CSIR, Trivandrum 695 019, India
Fax: +91(471)2491712; e-Mail: vijaynair_2001@yahoo.com;
^b Central Salt and Marine Chemicals Research Institute (CSIR), Bhavnagar 364 002, India

Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

References

For reviews, see:

<A NAME="RZ25807SS-1A">1a</A> Enders D. Balensiefer T. Acc. Chem. Res. 2004, 37: 534

<A NAME="RZ25807SS-1B">1b</A> Nair V. Bindu S. Sreekumar V. Angew. Chem. Int. Ed. 2004, 43: 5130

<A NAME="RZ25807SS-1C">1c</A> Cheng Y. Meth-Cohn O. Chem. Rev. 2004, 104: 2507

<A NAME="RZ25807SS-1D">1d</A> Zeitler K. Angew. Chem. Int. Ed. 2005, 44: 7506

<A NAME="RZ25807SS-1E">1e</A> Marion N. Diez-Gonzalez S. Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988

<A NAME="RZ25807SS-2">2</A> Breslow R. J. Am. Chem. Soc. 1958, 80: 3719

<A NAME="RZ25807SS-3">3</A> Wanzlick H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1: 75

<A NAME="RZ25807SS-4">4</A> Arduengo AJ. Harlow RL. Kline MK. J. Am. Chem. Soc. 1991, 113: 361

<A NAME="RZ25807SS-5A">5a</A> Enders D. Niemeier O. Balensiefer T. Angew. Chem. Int. Ed. 2006, 45: 1463

<A NAME="RZ25807SS-5B">5b</A> Hachisu Y. Bode JW. Suzuki K. J. Am. Chem. Soc. 2003, 125: 8432

<A NAME="RZ25807SS-6A">6a</A> Grasa GA. Kissling RM. Nolan SP. Org. Lett. 2002, 4: 3583

<A NAME="RZ25807SS-6B">6b</A> Grasa GA. Güveli T. Singh R. Nolan SP. J. Org. Chem. 2003, 68: 2812

<A NAME="RZ25807SS-6C">6c</A> Nyce GW. Lamboy JA. Connor EF. Waymouth JL. Hedrick RM. Org. Lett. 2002, 4: 3587

<A NAME="RZ25807SS-6D">6d</A> Singh R. Kissling RM. Letellier M.-A. Nolan SP. J. Org. Chem. 2004, 69: 209

<A NAME="RZ25807SS-7A">7a</A> Teles JH. Melder JP. Ebel K. Schneider GE. Harder W. Brode S. Enders D. Breuer K. Rabbe G. Helv. Chim. Acta 1996, 79: 1271

<A NAME="RZ25807SS-7B">7b</A> Davis JH. Forrester K. Tetrahedron Lett. 1999, 40: 1621

<A NAME="RZ25807SS-7C">7c</A> Enders D. Breuer K. Runsink J. Teles JH. Helv. Chim. Acta 1996, 79: 1899

<A NAME="RZ25807SS-8A">8a</A> Regitz M. Angew. Chem., Int. Ed. Engl. 1996, 35: 725

<A NAME="RZ25807SS-8B">8b</A> Bourissou D. Guerret O. Gabbai FP. Betrand G. Chem. Rev. 2000, 100: 39

<A NAME="RZ25807SS-9A">9a</A> Sohn SS. Rosen EL. Bode JW. J. Am. Chem. Soc. 2004, 126: 14370

<A NAME="RZ25807SS-9B">9b</A> Burstein C. Glorius F. Angew. Chem. Int. Ed. 2004, 43: 6205

<A NAME="RZ25807SS-9C">9c</A> Nair V. Vellalath S. Poonoth M. Suresh E. J. Am. Chem. Soc. 2006, 128: 8736

<A NAME="RZ25807SS-9D">9d</A> Christmann M. Angew. Chem. Int. Ed. 2005, 44: 2632

<A NAME="RZ25807SS-10A">10a</A> Nair V. Bindu S. Sreekumar V. Rath NP. Org. Lett. 2003, 5: 665

<A NAME="RZ25807SS-10B">10b</A> Nair V. Sreekumar V. Bindu S. Suresh E. Org. Lett. 2005, 7: 2299

<A NAME="RZ25807SS-11A">11a</A> Ma C. Yang Y. Org. Lett. 2005, 7: 1343

<A NAME="RZ25807SS-11B">11b</A> Ma C. Ding H. Zhang Y. Bian M. Angew. Chem. Int. Ed. 2006, 45: 1

<A NAME="RZ25807SS-12A">12a</A> Enders D. Breuer K. Rabbe G. Runsink J. Teles JH. Melder J.-P. Ebel K. Brode S. Angew. Chem. Int. Ed. 1995, 34: 1021

<A NAME="RZ25807SS-12B">12b</A> Enders D. Breuer K. Rabbe G. Runsink J. Teles JH. Liebigs Ann. Chem. 1996, 2019

<A NAME="RZ25807SS-12C">12c</A> Enders D. Breuer K. Kallfass U. Balensiefer T. Synthesis 2003, 1292

<A NAME="RZ25807SS-13">13</A> Knight RL. Leeper F. J. Chem. Soc., Perkin Trans. 1 1998, 1891

<A NAME="RZ25807SS-14">14</A> Enders D. Kallfass U. Angew. Chem. Int. Ed. 2002, 41: 1743

<A NAME="RZ25807SS-15A">15a</A> Kerr MS. Read de Alainz J. Rovis T. J. Am. Chem. Soc. 2002, 124: 10298

<A NAME="RZ25807SS-15B">15b</A> Kerr MS. Rovis T. Synlett 2003, 1934

<A NAME="RZ25807SS-15C">15c</A> Pesch J. Harms K. Bach T. Eur. J. Org. Chem. 2004, 2025

<A NAME="RZ25807SS-16A">16a</A> Nair V. Rajesh C. Vinod AU. Bindu S. Sreekanth AR. Mathen JS. Balagopal L. Acc. Chem. Res. 2003, 36: 899

<A NAME="RZ25807SS-16B">16b</A> Pillai AN. Devi BR. Suresh E. Nair V. Tetrahedron Lett. 2007, 48: 4391

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.