The information on reactions of nitrophenylethenes with azomethine ylides is very limited. It is only known that 1-nitro-2-phenylethene reacted with N-(2-methyl5-methoxycarbonylfur-3-yl)methyl-isoquinolinium bromide giving a product of 1,3-dipolar cycloaddition, 1-nitro-2-phenyl-3-R-2,3-dihydrobenzo[g]indolizine in a low yield [1]. In order to test the general character of this reaction we attempted to extend it to a new type of dipolarophile, 1-nitro-2-phenyl-1-cyano-ethene (I), and its analog, 1-bromo-1-nitro-2-phenylethene (II). It was established that phenylethenes I and II reacted with the precursors of azomethine ylides, N-phenacyl(III) or N-acetonylisoquinolinium bromides (IV), giving 1-nitro-2-phenyl-1,2,3,10b-tetrahydropyrrolo[2,1-a] isoquinolines V–VIII. It is presumable that at treating the N-onium salts III and IV with sodium hydride in dry dioxane active azomethine ylides A are generated [2] which as a result of 1,3-dipolar cycloaddition to molecules of dipolarophiles I or II are stabilized in the form of substituted tetrahydropyrroloisoquinolines V–VIII in 55–62% yield. The structure of compounds was confi rmed by IR and 1H NMR spectra, and the composition, by elemental analysis data. The IR spectra contain strong absorption bands of the stretching vibrations of the NO2 group at 1555 (νas), 1380 cm–1 (νs), and of C=O group at 1710 cm–1. In cycloadducts V and VI in contrast to initial phenylethene I (2225 cm–1) the absorption bands of the CN group are shifted in the longwave direction (2250 cm–1) with decrease in the intensity, apparently due to the stronger steric hindrances in the fi nal products. The parameters of the 1H NMR spectra are consistent with the assumed structures and are close to those of model compounds of similar structures from the series of pyrrolidine and isoquinoline [3, 4]. For instance, the protons of the pyrrolidine ring appear in the region 4.35–5.67 ppm, and the signals of protons H5 and H6 of the isoquinoline ring, at 6.57 and 6.35 ppm respectively (Scheme 1). The presence of a carbonyl group in the cycloadducts V–VIII provided a possibility to carry out a heterocyclization involving hydrazine hydrate to obtain previously unknown substituted 1-nitro-2-phenyl-2,2a,5,5a,6,10bhexahydrotriazinoindolizine IX–XII (Scheme 2). It is presumable that the reaction proceeds through the formation of intermediate hydrazone derivatives of pyrrolidine B which undergo a spontaneous heterocyclization