Synthesis and reactivity against Cp2TiCl of 4-isoprenyl-β-lactams. Trapping of N-titanoimidoyl radicals from cyanoformyl-2-azetidinones
| Autor: | Josefa Anaya, Laura M. Monleón, Ramón M. Sánchez, Manuel Grande |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement 010405 organic chemistry Chemistry Radical Organic Chemistry 010402 general chemistry Citral 01 natural sciences Biochemistry Medicinal chemistry Aldehyde 0104 chemical sciences chemistry.chemical_compound Reagent Drug Discovery Side chain Reactivity (chemistry) Staudinger reaction |
| Zdroj: | Tetrahedron. 74:5415-5426 |
| ISSN: | 0040-4020 |
| Popis: | A Staudinger reaction between methoxyketene and two different imines formed from citral afforded, after chemical transformation, the (E/Z)-4-alkenylepoxy-2-azetidinones 2, 3 and 4. These compounds, by reaction with Cp2TiCl, did not cyclize to afford the expected polycyclic β-lactams, but the corresponding allylic alcohols 12, 13 and 15 were obtained instead. Unexpectedly, the treatment of cyanoepoxide (E)-3 with Cp2TiCl also gave the hydroxyl aldehyde (E)-14 whose formation suggests to us that a possible radical reduction of the cyano group might have occurred, and we lastly succeeded in the capture of the N-titanoimidoyl radicals. The behaviour observed for the isoprenoid side chain in the Staudinger reaction, the reactions with Cp2TiCl, as well as the trapping of N-titanoimidoyl radicals generated from benzocyanoformyl-2-azetidinones with the Ti(III) reagent, are discussed. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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