Collect. Czech. Chem. Commun.
1991, 56, 673-684
https://doi.org/10.1135/cccc19910673
1,3-dipolar cycloadditions of heterocyclic nitrile oxides to substituted N-phenylmaleinimides
Eva Jedlovskáa, Lubor Fišeraa, Igor Goljerb, Mária Konopíkováa and Leonid I. Belenkiic
a Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Technical University, 812 37 Bratislava, Czechoslovakia
b Central Laboratory of NMR Spectroscopy, Faculty of Chemical Technology, Slovak Technical University, 812 37 Bratislava, Czechoslovakia
c Institute of Organic Chemistry, Academy of Sciences U.S.S.R., 117913 Moscow, U.S.S.R
Abstract
Cycloadditions of 2-furannitrile oxide (Ia), 5-nitro-2-furannitrile oxide (Ib), 5-(3-nitrophenyl)-2-furannitrile oxide (Ic), 5-(4-nitrophenyl)-2-furannitrile oxide (Id), and 2,5-dimethyl-3-dimethl-3-furannitrile oxide (Ie) with 4- or 2,6-disubstituted N-phenylmaleinimide are described. Investigated were also cycloadditions of 2,5-dimethyl-3-thiophenenitrile oxide (IVa), 2,4,5-trimethyl-3-thiophenenitrile oxide (IVb), 2,3-dimethyl-4-ethyl-3-thiophenenitrile oxide (IVc), 2,5-dimethyl-4-(1-methylethyl)-3-thiophenenitrile oxide (IVd), and 3,5-di(1,1-dimethylethyl)-2-thiophenenitrile oxide (V) with N-(2,6-dimethylphenyl)maleinimide. The steric course of these reactions is discussed.
