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

doi:10.1002/ejoc.201800356

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	3236-3244
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	24
DOIs	https://doi.org/10.1002/ejoc.201800356
Publication status	Published - 29 Jun 2018

Keywords

Alkylcarbonate
Green chemistry
Guanidine
Ion-molecule reactions
Ionic liquids
Recyclability

Access to Document

10.1002/ejoc.201800356

https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201800356

Cite this

@article{40f4f2efaa454aa68a261dfb467ee938,

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

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).",

keywords = "Alkylcarbonate, Green chemistry, Guanidine, Ion-molecule reactions, Ionic liquids, Recyclability",

author = "D{\'a}vid Isp{\'a}n and Eszter Sz{\'a}nti-Pint{\'e}r and Mat{\'e} Papp and Johan Wouters and Nikolay Tumanov and \{Bal{\'a}zs Zsirka\}, Bal{\'a}zs and {\'A}gnes G{\"o}m{\"o}ry and L{\'a}szl{\'o} Koll{\'a}r and Rita Skoda-F{\"o}ldes",

note = "Funding Information: The support of the National Research, Development and Innovation Office (OTKA 116727 and 120014) is acknowledged. This work is supported by the {\'U}NKP-17-2 New National Excellence Program of the Ministry of Human Capacities. X-ray diffraction data were recorded within the Plateforme de caract{\'e}risation PC2 at UNamur. Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

year = "2018",

month = jun,

day = "29",

doi = "10.1002/ejoc.201800356",

language = "English",

volume = "2018",

pages = "3236--3244",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "24",

}

TY - JOUR

T1 - The Use of Switchable Polarity Solvents for the Synthesis of 16‐Arylidene Steroids via Claisen–Schmidt Condensation

AU - Ispán, Dávid

AU - Szánti-Pintér, Eszter

AU - Papp, Maté

AU - Wouters, Johan

AU - Tumanov, Nikolay

AU - Balázs Zsirka, Balázs

AU - Gömöry, Ágnes

AU - Kollár, László

AU - Skoda-Földes, Rita

N1 - Funding Information: The support of the National Research, Development and Innovation Office (OTKA 116727 and 120014) is acknowledged. This work is supported by the ÚNKP-17-2 New National Excellence Program of the Ministry of Human Capacities. X-ray diffraction data were recorded within the Plateforme de caractérisation PC2 at UNamur. Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2018/6/29

Y1 - 2018/6/29

N2 - 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).

AB - 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).

KW - Alkylcarbonate

KW - Green chemistry

KW - Guanidine

KW - Ion-molecule reactions

KW - Ionic liquids

KW - Recyclability

UR - http://www.scopus.com/inward/record.url?scp=85049256313&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201800356

DO - 10.1002/ejoc.201800356

M3 - Article

SN - 1434-193X

VL - 2018

SP - 3236

EP - 3244

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 24

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Embargoed Document

Fingerprint

Physical Chemistry and characterization(PC2)

CCDC 1815278: Experimental Crystal Structure Determination

CCDC 1815277: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

Access to Document

Other files and links

Embargoed Document

Fingerprint

Equipment

Physical Chemistry and characterization(PC2)

Datasets

CCDC 1815278: Experimental Crystal Structure Determination

CCDC 1815277: Experimental Crystal Structure Determination

Cite this