Microwave-Assisted Stereoselective Heterocyclization to Novel Ring d-fused Arylpyrazolines in the Estrone Series
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Information
3.2. Synthetic Procedures
3.2.1. MW-assisted Synthesis of 3-methoxy-16-benzylidene-estra-1,3,5(10)-triene-17-one (2)
3.2.2. Cyclization of 3-methoxy-16-benzylidene-estra-1,3,5(10)-triene-17-one (2) with hydrazine hydrate
3.2.3. E2-type dehydration of mestranol to 17-ethinyl-3-methoxyestra-1,3,5(10),16-tetraene intermediate 12 by Method B
3.2.4. MW-Assisted Syntheses of 3-methoxy-19-norpregna-1,3,5(10),16-tetraene-20-one (13)
3.2.5. General Procedure for the Synthesis of Ring d-condensed Pyrazolines 17a–j under MW Irradiation
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Entry | Ar-NH-NH2 | Ar | Product | Yield 1 (%) |
---|---|---|---|---|
1 | 15a | Ph | 17a | 89 |
2 | 15b | 4-CH3-C6H4 | 17b | 95 |
3 | 15c | 2-CH3-C6H4 | 17c | 75 |
4 | 15d | 2,4-diCH3-C6H3 | 17d | 80 |
5 | 15e | 4-F-C6H4 | 17e | 88 |
6 | 15f | 4-Cl-C6H4 | 17f | 81 |
7 | 15g | 4-Br-C6H4 | 17g | 83 |
8 | 15h | 4-CN-C6H4 | 17h | 85 |
9 | 15i | 4-NO2-C6H4 | 17i | 80 |
10 | 15j | 4-MeO-C6H4 | 17j | 82 |
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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. https://doi.org/10.3390/molecules24030569
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(3):569. https://doi.org/10.3390/molecules24030569
Chicago/Turabian StyleMótyán, Gergő, Barnabás Molnár, János Wölfling, and Éva Frank. 2019. "Microwave-Assisted Stereoselective Heterocyclization to Novel Ring d-fused Arylpyrazolines in the Estrone Series" Molecules 24, no. 3: 569. https://doi.org/10.3390/molecules24030569