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Enolates of 2-Isothiocyanatocarboxylic Esters: Synthesis of Thiazolo[5,4-d]-thiazole Derivatives and 2-Thioxo-1,3-thiazolidine-4-carboxylates
| Content Provider | Semantic Scholar |
|---|---|
| Author | Cież, Dariusz Kalinowska-Tłuścik, Justyna |
| Copyright Year | 2012 |
| Abstract | An oxidative dimerization of titanium(IV) enolates derived from menthyl esters of 2-isothiocarboxylic acids leads to radical coupling followed by cyclization. This cascade reaction gives thiazolo[5,4-d]thiazole derivatives as pure enantiomers. Under similar conditions, 2-methylbutyl esters of 2-isothiocyanatocarboxylic acids undergo intermolecular oxidative dimerization to give mixtures of thiazolo[5,4-d]thiazoles and 2,3-diisothiocyanatosuccinates. Application of the soft enolization technique to dimethyl α,α′-diisothiocyanatodicarboxylic esters gives novel cyclic 1,2-diisothiocyanato-1,2-dicarboxylates. Sodium enolates of 2-isothiocyanatocarboxylates, on the other hand, form 5-imino-2-thioxo-1,3-thiazolidine-4-carboxylic esters by nonoxidative dimerization. The mechanisms of the two reaction pathways are discussed. |
| Starting Page | 1736 |
| Ending Page | 1744 |
| Page Count | 9 |
| File Format | PDF HTM / HTML |
| DOI | 10.1055/s-0031-1290825 |
| Alternate Webpage(s) | https://www.thieme-connect.de/media/synthesis/201211/supmat/sup_ss-2012-z0069-op_10-1055_s-0031-1290825.pdf |
| Alternate Webpage(s) | https://doi.org/10.1055/s-0031-1290825 |
| Volume Number | 44 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
