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Molecules 2019, 24(3), 569; https://doi.org/10.3390/molecules24030569

Microwave-Assisted Stereoselective Heterocyclization to Novel Ring d-fused Arylpyrazolines in the Estrone Series

Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary
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Academic Editor: John Spencer
Received: 28 January 2019 / Revised: 1 February 2019 / Accepted: 4 February 2019 / Published: 4 February 2019
(This article belongs to the Special Issue Microwave-mediated Chemistry)
Full-Text   |   PDF [1886 KB, uploaded 11 February 2019]   |  

Abstract

Microwave-assisted syntheses of novel ring d-condensed 2-pyrazolines in the estrone series were efficiently carried out from steroidal α,β-enones and hydrazine derivatives. The ring-closure reaction of 16-benzylidene estrone 3-methyl ether with hydrazine in acetic acid resulted in a 2:1 diastereomeric mixture of two 16,17-cis fused pyrazolines, which is contrary to the former literature data for both stereoselectivity and product structure. However, the cyclization reactions of a mestranol-derived unsaturated ketone with different arylhydrazines in acidic ethanol furnished the heterocyclic products in good to excellent yields independently of the substituents present on the aromatic ring of the reagents applied. The MW conditions also permitted the ring-closure reaction with p-nitrophenylhydrazine which is unfavorable under conventional heating. Moreover, the transformations led to the heterocyclic compounds stereoselectively with a 16α,17α-cis ring junction without being susceptible to spontaneous and promoted oxidation to pyrazoles. View Full-Text
Keywords: arylpyrazolines; heterocyclization; microwave; stereoselectivity; steroids arylpyrazolines; heterocyclization; microwave; stereoselectivity; steroids
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Mótyán, G.; Molnár, B.; Wölfling, J.; Frank, É. Microwave-Assisted Stereoselective Heterocyclization to Novel Ring d-fused Arylpyrazolines in the Estrone Series. Molecules 2019, 24, 569.

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