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Paper | Regular issue | Vol 68, No. 5, 2006, pp.949-966
Published online, 24th March, 2006
DOI: 10.3987/COM-06-10688
Synthesis of Methyl 2-[(Benzyloxycarbonyl)amino]-3-cyanopropenoate and Its Transformations into Derivatives of Pyrrole, 2,5-Dioxoimidazolidine, 1H-Pyrazole, and 4,6-Diaminopyridazine

Uros Ursic, David Bevk, Renata Toplak, Uros Groselj, Anton Meden, Jurij Svete,* and Branko Stanovnik*

*Department of Organic Chemistry, Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SI-1000 Ljubljana, Slovenia


Methyl (E)-2-[(benzyloxycarbonyl)amino]-3-cyanopropenoate (4) was, as a versatile multifunctional reagent, transformed with hydrazine and monosubstituted aromatic and heteroaromatic hydrazines under various conditions into derivatives of pyridazine (6), pyrrole (7), imidazole-2,4-dione (9), and pyrazole (13).