in Wiley InterScience (www.interscience.wiley.com).The 1,3-dipolar cycloaddition of unstabilized azomethine ylide 1 with meta-dinitrobenzene fused with nitrogen heterocycles affords the corresponding decahydropyrrolo[3,4-e]isoindole cycloadducts in good yields. This is a first example of [3þ2]-cycloaddition of azomethine ylides to nitroarenes.
The 1,3‐dipolar cycloaddition of unstabilized N‐methyl azomethine ylide to mononitro benzazoles was studied. Depending on the nature of substituents and annelated azoles, the reaction affords previously unknown isoindole fused heterocyclic systems. The reactivity of the cycloadducts was examined. J. Heterocyclic Chem., (2011).
Synthetic approaches to 1,3-dipolar cycloaddition of N-methylazomethinylid to mononitrobenzazole are described. The geometric and electronic structures have been studied by quantum chemical methods (HF/STO-3G and B3LYP/6-31G*) and the reactivity indexes of compounds have been estimated. It was shown that 1,3-dipolar cycloaddition of N-methylazomethinylid to the dipolarophile has a polar character and proceeds in accordance with the normal (noninversion) electronic distribution.Keywords: aromatic nitro compounds, reactivity indexes, quantum chemical calculations, methods HF/STO-3G and B3LYP/631G*, [3+2] cycloaddition mechanism of 1,3-dipolar cycloaddition,.
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