Please use this identifier to cite or link to this item: https://repository.udca.edu.co/handle/11158/2263
Title: A concise synthesis of a highly substituted 6-(1H-benzimidazol-1-yl)-5-nitrosopyrimidin-2- amine: Synthetic sequence and the molecular and supramolecular structures of one product and two intermediates
Authors: Cobo, Justo
Vicentes, Daniel E.
Rodríguez, Ricaurte
Marchal, Antonio
Glidewell, Christopher
Issue Date: 2018
Citation: Cobo, J., Vicentes, D. E., Rodríguez, R., Marchal, A., & Glidewell, C. (2018). A concise synthesis of a highly substituted 6-(1H-benzimidazol-1-yl)-5-nitrosopyrimidin-2- amine: Synthetic sequence and the molecular and supramolecular structures of one product and two intermediates. Acta Crystallographica Section C: Structural Chemistry, 74, 696-702. doi:10.1107/S2053229618007015
Series/Report no.: Acta Crystallographica Section C: Structural Chemistry;Vol.74, 2018 páginas 696-702
Abstract: A concise and efficient synthesis of 6-benzimidazolyl-5-nitrosopyrimidines has been developed using Schiff base-type intermediates derived from N4-(2-aminophenyl)-6-methoxy-5-nitrosopyrimidine-2,4-diamine. 6-Methoxy-N4-{2-[(4-methylbenzylidene)amino]phenyl}-5-nitrosopyrimidine-2,4-diamine, (I), and N4-{2-[(ethoxymethylidene)amino]phenyl}-6-methoxy-5-nitrosopyrimidine-2,4-diamine, (III), both crystallize from dimethyl sulfoxide solution as the 1:1 solvates C19H18N6O2·C2H6OS, (Ia), and C14H16N6O3·C2H6OS, (IIIa), respectively. The interatomic distances in these intermediates indicate significant electronic polarization within the substituted pyrimidine system. In each of (Ia) and (IIIa), intermolecular N-H…O hydrogen bonds generate centrosymmetric four-molecule aggregates. Oxidative ring closure of intermediate (I), effected using ammonium hexanitratocerate(IV), produced 4-methoxy-6-[2-(4-methylphenyl-1H-benzimidazol-1-yl]-5-nitrosopyrimidin-2-amine, C19H16N6O2, (II) [Cobo et al. (2018). Private communication (CCDC 1830889). CCDC, Cambridge, England], where the extent of electronic polarization is much less than in (Ia) and (IIIa). A combination of N–H…N and C–H…O hydrogen bonds links the molecules of (II) into complex sheets.
URI: https://www.scopus.com/search/form.uri?display=basic
Appears in Collections:CCB. Artículos indexados en Scopus

Files in This Item:
File Description SizeFormat 
A concise synthesis of a highly substituted.pdf
  Restricted Access
1,22 MBAdobe PDFView/Open Request a copy


This item is licensed under a Creative Commons License Creative Commons