A concise and efficient synthesis of amino-substituted (1H-benzo[d]imidazol-1-yl)pyrimidine hybrids: Synthetic sequence and the molecular and supramolecular structures of six examples
A concise and efficient synthesis of a series of amino-substituted benzimidazole-pyrimidine hybrids has been developed, starting from the readily available N 4-(2-aminophenyl)-6-methoxy-5-nitrosopyrimidine-2,4-diamine. In each of N 5-benzyl-6-methoxy-4-(2-phenyl-1H-benzo[d]imidazol-1-yl)pyrimidine-2...
- Autores:
-
Vicentes, Daniel E.
Rodríguez, Ricaurte
Ochoa, Patricia
Cobo, Justo
Glidewell, Glidewelld
- Tipo de recurso:
- Article of journal
- Fecha de publicación:
- 2019
- Institución:
- Universidad de Ciencias Aplicadas y Ambientales U.D.C.A
- Repositorio:
- Repositorio Institucional UDCA
- Idioma:
- eng
- OAI Identifier:
- oai:repository.udca.edu.co:11158/2462
- Acceso en línea:
- https://www.scopus.com/search/form.uri?display=basic
- Palabra clave:
- Enlaces de Hidrógeno
Carbón Orgánico
Bencimidazoles
Conformación Molecular
Benzimidazole
Crystal structure
Disorder
Hydrogen bonding
Molecular conformation
NMR spectra
Pyrimidine
Supramolecular assembly
Synthesis
- Rights
- openAccess
- License
- Derechos Reservados - Universidad de Ciencias Aplicadas y Ambientales
Summary: | A concise and efficient synthesis of a series of amino-substituted benzimidazole-pyrimidine hybrids has been developed, starting from the readily available N 4-(2-aminophenyl)-6-methoxy-5-nitrosopyrimidine-2,4-diamine. In each of N 5-benzyl-6-methoxy-4-(2-phenyl-1H-benzo[d]imidazol-1-yl)pyrimidine-2,5-diamine, C25H22N6O, (I), 6-methoxy-N 5-(4-methoxybenzyl)-4-[2-(4-methoxyphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, C27H26N6O3, (III), 6-methoxy-N 5-(4-nitrobenzyl)-4-[2-(4-nitrophenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, C25H20N8O5, (IV), the molecules are linked into three-dimensional framework structures, using different combinations of N-H⋯N, N-H⋯O, C-H⋯O, C-H⋯N and C-H⋯π hydrogen bonds in each case. Oxidative cleavage of 6-methoxy-N 5-(4-methylbenzyl)-4-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, (II), with diiodine gave 6-methoxy-4-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, which crystallized as a monohydrate, C19H18N6O·H2O, (V), and reaction of (V) with trifluoroacetic acid gave two isomeric products, namely N-{5-amino-6-methoxy-6-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidin-2-yl}-2,2,2-trifluoroacetamide, which crystallized as an ethyl acetate monosolvate, C21H17F3N6O2·C4H8O2, (VI), and N-{2-amino-6-methoxy-4-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidin-5-yl}-2,2,2-trifluoroacetamide, which crystallized as a methanol monosolvate, C21H17F3N6O2·CH4O, (VIIa). For each of (V), (VI) and (VIIa), the supramolecular assembly is two-dimensional, based on different combinations of O-H⋯N, N-H⋯O, N-H⋯N, C-H⋯O and C-H⋯π hydrogen bonds in each case. Comparisons are made with some related structures. |
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