An efficient and convenient one-step method for the synthesis of decahydrodipyrrolo [3,4-b:3',4'-d]pyridine derivatives was developed on the basis of 1,3-dipolar cycloaddition of unstabilized N-methyl azomethine ylide with 2-substituted 3,5-dinitropyridines. This novel heterocyclic system contains two 3-nitropyrrolidine fragments fused to a partially saturated pyridine ring. Such types of compound, as follows from the literature, can be considered as potential nitric oxide donors.

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A number of novel 6-R-isoxazolo[4,3-b]pyridines were synthesized and their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, π-excessive (het)arenes, dienes) were studied. The reaction rate was found to be dependent on the nature of the substituent 6-R. The most reactive 6-nitroisoxazolo[4,3-b]pyridines are able to add C-nucleophiles in the absence of a base under mild conditions. In addition, these compounds readily undergo [4+2]-cycloaddition reactions on aromatic bonds C=C(NO2) of the pyridine ring, thus indicating the superelectrophilic nature of 6-NO2-isoxazolo[4,3-b]pyridines.

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