Process for the synthesis of N-hydroxypyrroles, N-hydroxyimidazoles, and derivatives thereof
US4006160A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | May 19, 1975 |
| Grant date | Feb 1, 1977 |
| Priority date | — |
| Expiry date | May 19, 1995 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D207/34
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A process is described for the preparation of N-hydroxypyrrole-2-carbonitriles, N-hydroxyimidazole-2-carbonitriles, pyrrole-2-carbonitriles, and 3-substituted-2, 3-dihydro-2-pyrrolones by thermally decomposing 2-azidoheteroaromatic N-oxides. In the process a 2-azidoheteroaromatic N-oxide is heated in a suitable solvent for a period of time sufficient to bring the reaction to completion. Removal of the solvent by conventional methods gives the desired product. Which product is obtained is determined by the choice of solvents. In non-polar aprotic solvents, N-hydroxypyrrole-2-carbonitriles or N-hydroxyimidazole-2-carbonitriles are obtained. In nucleophilic solvents capable of undergoing Michael-type additions pyrrole-2-carbonitriles, imidazole-2-carbonitriles, and 3-substituted-2,3-dihydro-2-pyrrolone derivatives are obtained where a solvent molecule comprises the 3-substituent. These compounds are useful as anti-bacterials, e.g., against E. Coli.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.