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 1,3-Dipolar cycloadditions of heterocycles. V. Reaction of C-acetyl-N-phenylnitrilimine with furan derivatives

Ľ. Fišera, J. Kováč, J. Leško, and V. Šmahovský

Department of Organic Chemistry, Slovak Technical University, 880 37 Bratislava


Abstract:  1,3-Dipolar cycloaddition reactions of C-acetyl-iV-phenylnitrilimine with furan derivatives are described. 2-Methyl- and 2-ethylfuran afforded in addition to a byscycloadduct, a monocycloadduct, l-phenyl-3-acetyl-5-methyl(ethyl)-3a,6a-dihydrofuro[3,2-c]pyrazole. The reaction with furan re­sulted only in the bisadduct. As by-products, the dimer 3,6-diacetyl-l,4-diphenyl-l,4-dihydro-l,2,4?5-tetrazine and the products of decomposition of nitrilimine were isolated in all cases. The presence of the 1,3-addition product in the reaction mixture was not proved. The structures of the products were determined by 1H-n.m.r., u.V., and i.r. spectroscopy as well as by dehydrogenation of the monoadduct with DDQ under the formation of l-phenyl-3-acetyl-5-methylfuro[3,2-c]pyrazole.

Full paper in Portable Document Format: 351a93.pdf


Chemical Papers 35 (1) 93–104 (1981)

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