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

Verfasser / Beitragende:
[V. Chornous, O. Mel'nik, D. Mel'nik, E. Rusanov, M. Vovk]
Ort, Verlag, Jahr:
2015
Enthalten in:
Russian Journal of Organic Chemistry, 51/10(2015-10-01), 1423-1429
Format:
Artikel (online)
ID: 605529906
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024 7 0 |a 10.1134/S1070428015100115  |2 doi 
035 |a (NATIONALLICENCE)springer-10.1134/S1070428015100115 
245 0 0 |a 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  |h [Elektronische Daten]  |c [V. Chornous, O. Mel'nik, D. Mel'nik, E. Rusanov, M. Vovk] 
520 3 |a 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. 
540 |a Pleiades Publishing, Ltd., 2015 
700 1 |a Chornous  |D V.  |u Bukovinian State Medical University, Teatral'naya pl. 2, 58000, Chernovtsy, Ukraine  |4 aut 
700 1 |a Mel'nik  |D O.  |u Ivano-Frankovsk National Medical University, Galitskaya ul. 2, 76018, Ivano-Frankovsk, Ukraine  |4 aut 
700 1 |a Mel'nik  |D D.  |u Ivano-Frankovsk National Medical University, Galitskaya ul. 2, 76018, Ivano-Frankovsk, Ukraine  |4 aut 
700 1 |a Rusanov  |D E.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine  |4 aut 
700 1 |a Vovk  |D M.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine  |4 aut 
773 0 |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/10(2015-10-01), 1423-1429  |x 1070-4280  |q 51:10<1423  |1 2015  |2 51  |o 11178 
856 4 0 |u https://doi.org/10.1134/S1070428015100115  |q text/html  |z Onlinezugriff via DOI 
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950 |B NATIONALLICENCE  |P 856  |E 40  |u https://doi.org/10.1134/S1070428015100115  |q text/html  |z Onlinezugriff via DOI 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Chornous  |D V.  |u Bukovinian State Medical University, Teatral'naya pl. 2, 58000, Chernovtsy, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Mel'nik  |D O.  |u Ivano-Frankovsk National Medical University, Galitskaya ul. 2, 76018, Ivano-Frankovsk, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Mel'nik  |D D.  |u Ivano-Frankovsk National Medical University, Galitskaya ul. 2, 76018, Ivano-Frankovsk, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Rusanov  |D E.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Vovk  |D M.  |u Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02660, Kiev, Ukraine  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/10(2015-10-01), 1423-1429  |x 1070-4280  |q 51:10<1423  |1 2015  |2 51  |o 11178