Preparation of 1-substituted-5-[(2-oxo-2-phenyl)ethyl]imidazoles

Citation
P. Aulaskari et al., Preparation of 1-substituted-5-[(2-oxo-2-phenyl)ethyl]imidazoles, J HETERO CH, 37(1), 2000, pp. 87-93
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
37
Issue
1
Year of publication
2000
Pages
87 - 93
Database
ISI
SICI code
0022-152X(200001/02)37:1<87:PO1>2.0.ZU;2-2
Abstract
New high yield preparation methods were developed for the pharmaceutically interesting compounds, 1-benzyl-, 1-methyl-, and 1H-5-[(2-oxo-2-phenyl)ethy l]imidazoles 1a-c, respectively. The title compounds were synthesized by fo ur different methods using various starting materials. Two of the methods i nvolved transformation reactions of the key intermediates, 1-substituted-5- [(2-nitro-2-phenyl)ethenyl] imidazoles 2a-c and 1-substituted-5-[(2-nitro-2 -phenyl)ethyl]imidazoles 3a-c, while the other two utilized the oxidation o f 1-substituted-5-[(2-hydroxy-2-phenyl)ethyl]imidazoles 4a-c, with chromic oxide, and the umpolung reaction of benzaldehyde followed by a condensation reaction of the umpolung intermediate with imidazolecarboxaldehydes 6a-c.