Synthesis of Methyl (Z)-2-Acetamido-3-aryl-2-butenoates in Two Highly Selective Steps

C. Cativiela; M. D. Diaz De Villegas; E. Meléndez

doi:10.1055/s-1986-31660

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Synthesis 1986; 1986(5): 418-419
DOI: 10.1055/s-1986-31660

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Synthesis of Methyl (Z)-2-Acetamido-3-aryl-2-butenoates in Two Highly Selective Steps

C. Cativiela^* , M. D. Diaz De Villegas, E. Meléndez

^*Department of Organic Chemistry, University of Zaragoza. Zaragoza, Spain

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Publikationsdatum:
27. September 2002 (online)

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Diazomethane reacts with methyl (Z)-2-acetamido-3-aryl-2-propenoates regio- and stereospecifically to afford cis-4-aryl-3-acetamido-3-methoxycarbonyl-Δ¹-pyrazolines which heated in 1,2-ethanediol at 200°C extrude nitrogen to afford stereospecifically methyl (Z)-2-acetamido-3-aryl-2-butenoates in high yields.