caa a22 4500 605529906 CHVBK 20210128100820.0 cr unu---uuuuu 210128e20151001xx s 000 0 eng 10.1134/S1070428015100115 doi (NATIONALLICENCE)springer-10.1134/S1070428015100115 Polyfunctional imidazoles: XI. Reaction of 1-aryl-4-chloro-5-(2-nitrovinyl)-1 H -imidazoles with nonstabilized azomethine ylides. Synthesis of (1-aryl-4-chloro-1 H -imidazol-5-yl)-substituted nitropyrrolidines and nitropyrrolizines [Elektronische Daten] [V. Chornous, O. Mel'nik, D. Mel'nik, E. Rusanov, M. Vovk] 1-Aryl-4-chloro-5-(2-nitrovinyl)-1H-imidazoles reacted with azomethine ylide generated from sarcosine and formaldehyde to afford 1-aryl-4-chloro-5-(4-nitropyrrolidin-3-yl)-1H-imidazoles. The reaction of 1-aryl-4-chloro-5-(2-nitrovinyl)-1H-imidazoles with azomethine ylide generated from L-proline and isatin gave 2′-(1-aryl-4-chloro-1H-imidazol-5-yl)-1′-nitro-1′,2′,5′,6′,7′,7a′-octahydrospiro[indole-3,3′-pyrrolizin]-2(1H)-ones with high regioselectivity. The latter reaction was analyzed by calculating orbital coefficients and global and molecular reactivity indices of the dipole and dipolarophile, as well as the energies of the initial reactants, transition states, and products. Pleiades Publishing, Ltd., 2015 Chornous V. Bukovinian State Medical University, Teatral'naya pl. 2, 58000, Chernovtsy, Ukraine aut Mel'nik O. Ivano-Frankovsk National Medical University, Galitskaya ul. 2, 76018, Ivano-Frankovsk, Ukraine aut Mel'nik D. Ivano-Frankovsk National Medical University, Galitskaya ul. 2, 76018, Ivano-Frankovsk, Ukraine aut Rusanov E. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut Vovk M. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut Russian Journal of Organic Chemistry Pleiades Publishing 51/10(2015-10-01), 1423-1429 1070-4280 51:10<1423 2015 51 11178 https://doi.org/10.1134/S1070428015100115 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015100115 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Chornous V. Bukovinian State Medical University, Teatral'naya pl. 2, 58000, Chernovtsy, Ukraine aut NATIONALLICENCE 700 1- Mel'nik O. Ivano-Frankovsk National Medical University, Galitskaya ul. 2, 76018, Ivano-Frankovsk, Ukraine aut NATIONALLICENCE 700 1- Mel'nik D. Ivano-Frankovsk National Medical University, Galitskaya ul. 2, 76018, Ivano-Frankovsk, Ukraine aut NATIONALLICENCE 700 1- Rusanov E. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut NATIONALLICENCE 700 1- Vovk M. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/10(2015-10-01), 1423-1429 1070-4280 51:10<1423 2015 51 11178