Activation And Regioselectivity Of Five-Membered Cyclic Thionocarbamates To Nucleophilic Attack
| Autor: | Ismail Awheda, John D. Wallis, Nezire Saygili, A. Christopher Garner |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Stereochemistry General Chemical Engineering Iodide Regioselectivity chemistry.chemical_element General Chemistry 010402 general chemistry Ring (chemistry) Cleavage (embryo) 01 natural sciences Medicinal chemistry Sulfur 0104 chemical sciences 3. Good health chemistry Nucleophile Yield (chemistry) |
| ISSN: | 2046-2069 |
| Popis: | The cyclic thionocarbamate of alaninol undergoes nucleophilic attack by sulfur nucleophiles at 5-C to give 1-thiopropyl-2-amine derivatives when derivatised on nitrogen with a Boc group. Iodide under microwave conditions causes a rearrangement to the isomeric thiazolidinone, while “hard” nucleophiles react at the thione group to yield a variety of product types by subsequent C–N or C–O cleavage. X-ray crystallography studies showed that the N-Boc group reduces delocalisation of electron density from nitrogen into the thione group, and thus promotes activation of the ring to nucleophilic attack. |
| Databáze: | OpenAIRE |
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