Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol
| Autor: | Natalia B. Kilimciler, Liliana R. Orelli, Juan A. Bisceglia, Maria C. Mollo |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Trimethylsilyl Polyphosphate Organic Chemistry medium-size heterocycles Ring (chemistry) Microwave assisted Medicinal chemistry Full Research Paper microwaves lcsh:QD241-441 chemistry.chemical_compound Chemistry chemistry lcsh:Organic chemistry cyclodehydration lcsh:Q lcsh:Science 4-aminobutanol ppse tetrahydrothiazepines Alkyl |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 16, Iss 1, Pp 32-38 (2020) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| Popis: | A general procedure for the synthesis of 2-substituted tetrahydro-1,3-thiazepines by MW-assisted cyclization of 4-thioamidobutanols is presented. The acyclic precursors were prepared in high overall yields by an expeditious three-step diacylation/thionation/deprotection sequence from 4-aminobutanol. Microwave-assisted ring closure of 4-thioamido alcohols promoted by trimethylsilyl polyphosphate (PPSE) in solvent-free conditions allowed for the synthesis of several hitherto unreported seven-membered iminothioethers bearing 2-aryl, alkenyl, aralkyl and alkyl substituents. The cyclodehydration reaction is likely to involve an SN2-type displacement and affords good to excellent yields of the desired heterocycles in very short reaction times. |
| Databáze: | OpenAIRE |
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