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1,3-Dipolar cycloaddition reactions of 2-substituted 5-<i>R</i>-3-nitropyridines and isomeric 3-<i>R</i>-5-nitropyridines with N-methyl azomethine ylide were studied. The effect of the substituent at positions 2 and 5 of the pyridine ring on the possibility of the [3+2]-cycloaddition process was revealed. A number of new derivatives of pyrroline and pyrrolidine condensed with a pyridine ring were synthesized.