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

Dávid Ispán, Eszter Szánti-Pintér, Máté Papp, Johan Wouters, Nikolay Tumanov, Balázs Zsirka, A. Gömöry, L. Kollár, R. Skoda-Földes

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)3236-3244
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number24
DOIs
Publication statusPublished - Jun 29 2018

Fingerprint

steroids
Ethylene Glycol
Estranes
glycols
Condensation
polarity
ethylene
condensation
Steroids
Nuclear magnetic resonance
catalysts
nuclear magnetic resonance
Catalysts
synthesis
aldehydes
musculoskeletal system
Aldehydes
conductivity
products
butyl-1,1,3,3-tetramethylguanidine

Keywords

  • Alkylcarbonate
  • Green chemistry
  • Guanidine
  • Ion-molecule reactions
  • Ionic liquids
  • Recyclability

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

The Use of Switchable Polarity Solvents for the Synthesis of 16-Arylidene Steroids via Claisen–Schmidt Condensation. / Ispán, Dávid; Szánti-Pintér, Eszter; Papp, Máté; Wouters, Johan; Tumanov, Nikolay; Zsirka, Balázs; Gömöry, A.; Kollár, L.; Skoda-Földes, R.

In: European Journal of Organic Chemistry, Vol. 2018, No. 24, 29.06.2018, p. 3236-3244.

Research output: Contribution to journalArticle

Ispán, Dávid ; Szánti-Pintér, Eszter ; Papp, Máté ; Wouters, Johan ; Tumanov, Nikolay ; Zsirka, Balázs ; Gömöry, A. ; Kollár, L. ; Skoda-Földes, R. / The Use of Switchable Polarity Solvents for the Synthesis of 16-Arylidene Steroids via Claisen–Schmidt Condensation. In: European Journal of Organic Chemistry. 2018 ; Vol. 2018, No. 24. pp. 3236-3244.
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AU - Tumanov, Nikolay

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