Ring opening and closing reactions of imidazoles and other 1,3-diazaheterocycles with vinyl chloroformate and phenyl chloroformate
β Scribed by R.F. Pratt; K.K. Kraus
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 229 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Treatment of imidazole and benzimidazole with vinyl chloroformate or phenyl chloroformate in weakly alkaline aqueous solution leads to their conversion into the corresponding imidazol-Z-ones; in weakly acidic solutions these chloroformates convert adenine into isoguanine, 6methylaminopurine into 1-methylisoguanine and pyrimidine into an acyclic product.
π SIMILAR VOLUMES
It was.recently reported that dichlorocarbene, as generated from chloroform and sodium methexide, adds to an excess of cyclooctene (A), 1,3,6-cyclooctatriene (2), and 1,3,5-cyclooctatriene (J), as well as assorted alkyl, cycloalkyl, aryl and alkoxy derivatives, to give products with the bicyclo[4.2.
The N-benzyl-and N-alkyl-substituted 1,2-thiazetidin-3-one 1,1-dioxides 1b Β± d reacted readily with NH 3 and primary amines via ring opening. The reaction with NH 3 proceeded at Γ 788 3 room temperature yielding ring-opened adducts via nucleophilic attack of NH 3 at the sulfonyl group, whereas the r