The Use of Switchable Polarity Solvents for the Synthesis of 16‐Arylidene Steroids via Claisen–Schmidt Condensation

Dávid Ispán, Eszter Szánti-Pintér, Maté Papp, Johan Wouters, Nikolay Tumanov, Balázs Balázs Zsirka, Ágnes Gömöry, László Kollár, Rita Skoda-Földes

Résultats de recherche: Contribution à un journal/une revueArticleRevue par des pairs

Résumé

Switchable polarity recyclable solvent mixtures were applied as reaction medium and catalyst to replace the conventional base catalysts in the Claisen–Schmidt condensation of 17‐oxo steroids with aromatic aldehydes. Reversibility between ionic and nonionic forms of the new 2‐n‐butyl‐1,1,3,3‐tetramethylguanidine (nBu‐TMG)/ethylene glycol/CO2 and 2‐tert‐butyl‐1,1,3,3‐tetramethylguanidine (tBu‐TMG)/ethylene glycol/CO2 systems were proved by conductivity measurements. The structure of the ionic form was established by 1H NMR and IR measurements and by quantum chemical calculations. The steroidal products with androstane and estrane skeleton were characterised with spectroscopic methods (NMR, IR, MS).
langue originaleAnglais
Pages (de - à)3236-3244
Nombre de pages9
journalEuropean Journal of Organic Chemistry
Volume2018
Numéro de publication24
Les DOIs
Etat de la publicationPublié - 29 juin 2018

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