1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene (TBD) Triggered Diastereoselective [3+2] Cycloaddition of Azomethine Imines and Pyrazoleamides

1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene (TBD) Triggered Diastereoselective [3+2] Cycloaddition of Azomethine Imines and Pyrazoleamides

A practical and mild approach to prepare tetrahydropyrazolo[1,2‐a]‐pyrazole‐1,7‐diones, bearing up to three stereocentres, by reacting ready available N,N′‐cyclic azomethine imines and pyrazoleamides under catalytic loading of commercial 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD), has been developed....

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Veröffentlicht in:Advanced synthesis & catalysis 2019-03, Vol.361 (5), p.1018-1022
Hauptverfasser: Volpe, Chiara, Meninno, Sara, Capobianco, Amedeo, Vigliotta, Giovanni, Lattanzi, Alessandra
Format: Artikel
Sprache:eng
Schlagworte:
azomethine imines
bifunctional catalysis
Catalysis
Cycloaddition
heterocycles
Imines
Pyrazole
Stereoselectivity
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Zusammenfassung:A practical and mild approach to prepare tetrahydropyrazolo[1,2‐a]‐pyrazole‐1,7‐diones, bearing up to three stereocentres, by reacting ready available N,N′‐cyclic azomethine imines and pyrazoleamides under catalytic loading of commercial 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD), has been developed. The products are obtained in good yields and high diastereoselectivity, working at room temperature. Preliminary bioassay showed the products to inhibit growth of Gram‐positive bacteria.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201801567