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Nitropyridines as 2π-Partners in 1,3-Dipolar Cycloadditions with N-Methyl Azomethine Ylide: An Easy Access to Condensed Pyrrolines |
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| Authors: | Maxim A. Bastrakov Alexey K. Fedorenko Alexey M. Starosotnikov Alexander Kh. Shakhnes |
| Affiliation: | N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, 119991 Moscow, Russia; (A.K.F.); (A.M.S.); (A.K.S.) |
| Abstract: | 1,3-Dipolar cycloaddition reactions of 2-substituted 5-R-3-nitropyridines and isomeric 3-R-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. |
| Keywords: | nitro group nitropyridines pyrrolo[3 4-c]pyridines dearomatization 1 3-dipolar cycloadditition pyrrolidines azomethine ylides |