Reaction of enamines with semicarbazone-based amidoalkylating reagents: A straightforward synthesis of annulated 1-aminopyrimidin-2-one derivatives
| Autor: | Anatoly Shutalev, Anastasia A. Fesenko |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Double bond Bicyclic molecule 010405 organic chemistry Chemistry Organic Chemistry Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Cascade reaction Reagent Drug Discovery Isomerization Semicarbazone |
| Zdroj: | Tetrahedron Letters. 66:152826 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2021.152826 |
| Popis: | An efficient synthesis of 1-arylideneamino-substituted hexahydro-1H-cyclopenta[d]pyrimidin-2-ones and octahydroquinazolin-2-ones has been developed. The synthesis involves a stereo- and regioselective cascade reaction of the corresponding 4-(tosylmethyl)semicarbazones with 1-morpholinocyclopentene or 1-morpholinocyclohexene to give predominantly bicyclic pyrimidines with an exocyclic C C double bond (80–97%). The later undergo rapid isomerization when heated in THF in the presence of TsOH to form bicyclic pyrimidines with a significant predominance of those with an endocyclic C C double bond (90–97%). |
| Databáze: | OpenAIRE |
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