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
| Autor: | Daniel E. Vicentes, Justo Cobo, Ricaurte Rodríguez, Antonio Marchal, Christopher Glidewell |
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| Rok vydání: | 2018 |
| Předmět: |
Hydrogen bonding
Pyrimidine Stereochemistry Supramolecular chemistry Crystal structure 010402 general chemistry Ring (chemistry) Síntesis química Benzimidazole 01 natural sciences Inorganic Chemistry Synthesis chemistry.chemical_compound Materials Chemistry Molecule Supramolecular aggregation Physical and Theoretical Chemistry Bisbenzimidazol Enlaces de Hidrógeno chemistry.chemical_classification Heterocyclic compound Nitrosopyrimidine 010405 organic chemistry Hydrogen bond Condensed Matter Physics 0104 chemical sciences chemistry Estructura Molecular Amine gas treating Electronic polarization Molecular structure |
| Zdroj: | Repositorio Institucional UDCA Universidad de Ciencias Aplicadas y Ambientales U.D.C.A instacron:Universidad de Ciencias Aplicadas y Ambientales U.D.C.A |
| ISSN: | 2053-2296 |
| DOI: | 10.1107/s2053229618007015 |
| Popis: | A concise and efficient synthesis of 6-benzimidazolyl-5-nitrosopyrimidines has been developed using Schiff base-type intermediates derived from N 4-(2-aminophenyl)-6-methoxy-5-nitrosopyrimidine-2,4-diamine. 6-Methoxy-N 4-{2-[(4-methylbenzylidene)amino]phenyl}-5-nitrosopyrimidine-2,4-diamine, (I), and N 4-{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. |
| Databáze: | OpenAIRE |
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