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Synfacts 2006(11): 1102-1102
DOI: 10.1055/s-2006-949425
DOI: 10.1055/s-2006-949425
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
One-Pot Synthesis of 3,4-Disubstituted Pyrrole-2-Esters
A. Bhattacharya*, S. Cherukuri, R. E. Plata, N. Patel, V. Jr., Tamez, J. A. Grosso, M. Peddicord, V. A. Palaniswamy
Texas A&M University, Kingsville and Bristol Myers Squibb, New Brunswick, USA
Further Information
Publication History
Publication Date:
24 October 2006 (online)
Significance
As perhaps not uncommonly observed but rarely reported, an original procedure proceeds through several generations of improvement. In the reported case, it is also a progression in a generation of chemists. The method for the synthesis of 3,4-disubstituted pyrrole-2-esters, originally disclosed by Barton and Zard over 15 years ago (D. H. R. Barton, J. Kervagore, S. Zard Tetrahedron 1990, 21, 7587-7598), is now reported in an improved version. Under the new conditions, the reaction of β-acetoxy nitro derivatives and acetylenic esters with ethyl isocyanoacetate under acylative, base-mediated conditions leads to substituted pyrrolo carboxylates in good to excellent yields in a single pot.