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Synthesis 2008(1): 29-31
DOI: 10.1055/s-2007-1000824
DOI: 10.1055/s-2007-1000824
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
A Novel Synthesis of Highly Substituted But-2-enoic Acid Esters by the Reaction of DMAP-Methyl Phenylpropiolate Zwitterion and Diaryl 1,2-Diones
Further Information
Received
26 September 2007
Publication Date:
07 December 2007 (online)
Publication History
Publication Date:
07 December 2007 (online)

Abstract
This work describes a novel reaction involving 4-(N,N-dimethylamino)pyridine (DMAP)-methyl phenylpropiolate zwitterion and diaryl 1,2-diones, leading to the facile synthesis of substituted butenoic acid esters.
Key words
zwitterions - DMAP - methyl phenylpropiolate - benzil - diaryl 1,2-diones
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1a
Diels O.Alder K. Justus Liebigs Ann. Chem. 1932, 498: 16 -
1b
Winterfeldt E. Angew. Chem., Int. Ed. Engl. 1969, 6: 423 -
1c
Winterfeldt E. In Chemistry of AcetylenesViehe HG. Dekker; New York: 1969. p.267 -
1d
Dickstein JI.Miller SI. In The Chemistry of Functional Groups. The Chemistry of the Carbon-Carbon Triple Bond Part 2:Patai S. Wiley; Chichester: 1978. Chap. 19. p.813 -
1e
Acheson RM.Elmore NF. Adv. Heterocycl. Chem. 1978, 23: 263 -
2a
Nair V.Rajesh C.Vinod AU.Bindu S.Sreekanth AR.Mathen JS.Balagopal L. Acc. Chem. Res. 2003, 36: 899 -
2b
Nair V.Menon RS.Sreekanth AR.Abhilash N.Biju AT. Acc. Chem. Res. 2006, 39: 520 -
3a
Nair V.Vinod AU.Abhilash N.Menon RS.Santhi V.Varma RL.Viji S.Mathew S.Srinivas R. Tetrahedron 2003, 59: 10279 ; and references citied therein -
3b
Nair V.Sreekanth AR.Abhilash N.Bhadbhade MM.Gonnade RC. Org. Lett. 2002, 4: 3575 -
3c
Nair V.Pillai AN.Menon RS.Suresh E. Org. Lett. 2005, 7: 1189 -
3d
Nair V.Pillai AN.Beneesh PB.Suresh E. Org. Lett. 2005, 7: 4625 -
3e
Pillai AN.Devi BR.Suresh E.Nair V. Tetrahedron Lett. 2007, 48: 4391
References
Crystal data for 3a: Empirical formula: C24H18O4; Unit cell parameters: a = 8.332(9) Å, b = 8.609(10) Å, c = 14.263(16) Å, α = 76.913(18)°, β = 86.448(17)°, γ = 72.752(17)°; Space group P-1. CCDC 653243 contains the supplementary crystallographic data for compound 3a. These data can be obtained free of charge from The Cambridge Crystallog-raphic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.