Polyfunctional imidazoles: XI. Reaction of 1-aryl-4-chloro-5-(2-nitrovinyl)-1H-imidazoles with nonstabilized azomethine ylides. Synthesis of (1-aryl-4-chloro-1H-imidazol-5-yl)-substituted nitropyrrolidines and nitropyrrolizines View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2015-10

AUTHORS

V. A. Chornous, O. Ya. Mel’nik, D. A. Mel’nik, E. B. Rusanov, M. V. Vovk

ABSTRACT

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. More... »

PAGES

1423-1429

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428015100115

DOI

http://dx.doi.org/10.1134/s1070428015100115

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1020392486


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