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Synthesis 2008(1): 29-31  
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

Abhilash N. Pillaia, Eringathodi Sureshb, Vijay Nair*a,c
a Organic Chemistry Section, Regional Research Laboratory (CSIR), Trivandrum 695 019, India
b Central Salt and Marine Chemicals Research Institute (CSIR), Bhavnagar 364 002, India
c Jawaharlal Nehru Centre for Advanced Scientific Research, Bangalore 560 064, India
Fax: 91(471)2491712; e-Mail: vijaynair_2001@yahoo.com;
Further Information

Publication History

Received 26 September 2007
Publication Date:
07 December 2007 (online)

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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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4

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.