Method of preparation of halogenated diazines
US5304647A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Aug 24, 1990 |
| Grant date | Apr 19, 1994 |
| Priority date | — |
| Expiry date | Aug 24, 2010 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D409/14
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A method of preparation of substituted halogenodiazines which are useful as intermediates in the synthesis of novel unfused heterobicyclic compounds, and the products thereof. The reaction consists of the addition of an organolithium reagent with subsequent dehydrogenation of the addition product. The reaction takes place in one reaction vessel, without isolation of the substituted halogenodihydrodiazine intermediate. The reactions proceed at moderate temperature and in a short amount of time, which decreases the probability of side reactions and increases yield. Furthermore, the workup step is conducted under two-phase conditions to prevent hydrolysis of the substituted halogenodiazine to a substituted hydroxydiazine. The method is easy, efficient and results in a high yield of product. The substituted halogenodiazines are used as intermediates in the synthesis of unfused heterobicyclic compounds containing an aromatic moiety, diazine, and another aromatic moiety, such as thiophene, benzene, or naphthalene, which have biological activity.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.