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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
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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
Bibliographic description
| title: | Enolates of 2-isothiocyanatocarboxylic esters : synthesis of thiazolo[5,4-d]-thiazole derivatives and 2-thioxo-1,3-thiazolidine-4-carboxylates |
| author: | Cież Dariusz  , Kalinowska-Tłuścik Justyna
|
| journal title: | Synthesis |
| volume: | 44 |
| issue: | 11 |
| date of publication : | 2012 |
| pages: | 1736-1744 |
| ISSN: |
0039-7881 |
| eISSN: |
1437-210X |
| DOI: | |
| language: | English |
| journal language: | English |
| abstract in English: | 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 $\alpha$,$\alpha$′-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. |
| keywords in English: | domino reactions, heterocycles, dimerizations, enols, diastereoselectivity, titanium |
| departmental parameterization: | 25 |
| affiliation: | Wydział Chemii : Zakład Krystalochemii i Krystalofizyki, Wydział Chemii : Zakład Chemii Organicznej |
| type: | journal article |
| subtype: | academic paper |
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Projekt „Repozytorium otwartego dostępu do dorobku naukowego i dydaktycznego UJ” współfinansowany w ramach poddziałania 2.3.1 „Cyfrowe udostępnianie zasobów nauki” Programu Operacyjnego Polska Cyfrowa z Europejskiego Funduszu Rozwoju Regionalnego i budżetu państwa na podstawie umowy o dofinansowanie nr POPC.02.03.01-00-0030/17-00
