Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction
| Autor: | Shih-I Liu, Jia-Yun Haung, Chung-Ming Sun, Indrajeet J. Barve, Sheng-Cih Huang |
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| Rok vydání: | 2019 |
| Předmět: |
Hydantoin
Diketopiperazines 010402 general chemistry Chloroacetyl chloride 01 natural sciences Medicinal chemistry Catalysis chemistry.chemical_compound Tetrahydroisoquinolines Moiety Amines Aldehydes Pictet–Spengler reaction Nucleophilic addition Cycloaddition Reaction Molecular Structure 010405 organic chemistry Hydantoins Diastereomer Enantioselective synthesis Stereoisomerism General Chemistry General Medicine Condensation reaction 0104 chemical sciences chemistry Solvents |
| Zdroj: | ACS combinatorial science. 21(4) |
| ISSN: | 2156-8944 |
| Popis: | An enantioselective synthesis of iso-, isothio-, and isoselenohydantoin and diketopiperazine-fused tetrahydroisoquinolines from l-Dopa was reported. The route consists of an Pictet-Spengler reaction of ( S)-2-amino-3-(3,4-dimethoxyphenyl)propanoates with various aldehydes to afford diastereomeric tetrahydroisoquinolines. Next step, the tetrahydroisoquinolines were further reacted with iso-, isothio-, or isoselenocyanates to construct hydantoin. Similarly, the diketopiperazine moiety was constructed by subjecting tetrahydroisoquinolines to a condensation reaction with chloroacetyl chloride followed by nucleophilic addition with various primary amines. |
| Databáze: | OpenAIRE |
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