Temperature and steric hindrance-regulated selective synthesis of ketamine derivatives and 2-aryl-cycloketone-1-carboxamides nucleophilic substitution and Favorskii rearrangement.
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| Main Authors: | , , , |
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| Format: | Artículo científico |
| Language: | en |
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Organic & biomolecular chemistry
2025
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| _version_ | 1868266242343698433 |
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| author | Zhai, Haojiang Li, Penghui Wang, Hongshuang Wang, Xiaohui |
| author_facet | Zhai, Haojiang Li, Penghui Wang, Hongshuang Wang, Xiaohui Zhai, Haojiang Li, Penghui Wang, Hongshuang Wang, Xiaohui |
| collection | PubMed - marine biology |
| contents | Temperature and steric hindrance-regulated selective synthesis of ketamine derivatives and 2-aryl-cycloketone-1-carboxamides nucleophilic substitution and Favorskii rearrangement. Zhai, Haojiang Li, Penghui Wang, Hongshuang Wang, Xiaohui A selective temperature and steric hindrance-regulated method for nucleophilic substitution or Favorskii rearrangement reactions of 2-aryl-2-bromo-cycloketones with aliphatic amines has been developed to prepare ketamine derivatives and 2-aryl-cycloketone-1-carboxamides. In the presence of secondary amines or -substituted 2-aryl-2-bromocycloketones, steric hindrance directs the Favorskii rearrangement to occur. Conversely, with primary amines, the product ratio of nucleophilic substitution to Favorskii rearrangement is temperature-dependent, with higher temperatures favoring the Favorskii rearrangement. At lower temperatures (-25 °C or below), nucleophilic substitution predominates, yielding ketamine derivatives in yields of 60% to 85%. This method effectively utilizes temperature and steric hindrance to control the reaction pathway and optimize product formation. |
| format | Artículo científico |
| id | pubmed_39957341 |
| institution | PubMed |
| language | en |
| publishDate | 2025 |
| publisher | Organic & biomolecular chemistry |
| record_format | pubmed |
| spellingShingle | Temperature and steric hindrance-regulated selective synthesis of ketamine derivatives and 2-aryl-cycloketone-1-carboxamides nucleophilic substitution and Favorskii rearrangement. Zhai, Haojiang Li, Penghui Wang, Hongshuang Wang, Xiaohui Temperature and steric hindrance-regulated selective synthesis of ketamine derivatives and 2-aryl-cycloketone-1-carboxamides nucleophilic substitution and Favorskii rearrangement. Zhai, Haojiang Li, Penghui Wang, Hongshuang Wang, Xiaohui A selective temperature and steric hindrance-regulated method for nucleophilic substitution or Favorskii rearrangement reactions of 2-aryl-2-bromo-cycloketones with aliphatic amines has been developed to prepare ketamine derivatives and 2-aryl-cycloketone-1-carboxamides. In the presence of secondary amines or -substituted 2-aryl-2-bromocycloketones, steric hindrance directs the Favorskii rearrangement to occur. Conversely, with primary amines, the product ratio of nucleophilic substitution to Favorskii rearrangement is temperature-dependent, with higher temperatures favoring the Favorskii rearrangement. At lower temperatures (-25 °C or below), nucleophilic substitution predominates, yielding ketamine derivatives in yields of 60% to 85%. This method effectively utilizes temperature and steric hindrance to control the reaction pathway and optimize product formation. |
| title | Temperature and steric hindrance-regulated selective synthesis of ketamine derivatives and 2-aryl-cycloketone-1-carboxamides nucleophilic substitution and Favorskii rearrangement. |
| url | https://pubmed.ncbi.nlm.nih.gov/39957341/ |