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Journal articles on the topic 'Pyrazolidines'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Fernández, Maitane, Efraím Reyes, Jose L. Vicario, Dolores Badía, and Luisa Carrillo. "Organocatalytic Enantioselective Synthesis of Pyrazolidines, Pyrazolines and Pyrazolidinones." Advanced Synthesis & Catalysis 354, no. 2-3 (2012): 371–76. http://dx.doi.org/10.1002/adsc.201100722.

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2

Geng, Zhi-Cong, Jian Chen, Ning Li та ін. "Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives". Beilstein Journal of Organic Chemistry 8 (9 жовтня 2012): 1710–20. http://dx.doi.org/10.3762/bjoc.8.195.

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The catalytic synthesis of nitrogen-containing heterocycles is of great importance to medicinal and synthetic chemists, and also a challenge for modern chemical methodology. In this paper, we report the synthesis of pyrazolidine derivatives through a domino aza-Michael/hemiacetal sequence with chiral or achiral secondary amines as organocatalysts. Thus, a series of achiral pyrazolidine derivatives were obtained with good yields (up to 90%) and high diastereoselectivities (>20:1) with pyrrolidine as an organocatalyst, and enantioenriched pyrazolidines are also achieved with good results (up

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3

Fernandez, Maitane, Efraim Reyes, Jose L. Vicario, Dolores Badia, and Luisa Carrillo. "ChemInform Abstract: Organocatalytic Enantioselective Synthesis of Pyrazolidines, Pyrazolines and Pyrazolidinones." ChemInform 43, no. 26 (2012): no. http://dx.doi.org/10.1002/chin.201226120.

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4

Huang, Zhimei, Junhao Hu, and Yuefa Gong. "Formation and aromatization of strained bicyclic pyrazolidines via tandem reaction of alkyl 2-aroyl-1-chlorocyclopropanecarboxylates with acylhydrazones." Organic & Biomolecular Chemistry 13, no. 31 (2015): 8561–66. http://dx.doi.org/10.1039/c5ob01199j.

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5

Nájera, Carmen, José M. Sansano, and Miguel Yus. "1,3-Dipolar cycloadditions of azomethine imines." Organic & Biomolecular Chemistry 13, no. 32 (2015): 8596–636. http://dx.doi.org/10.1039/c5ob01086a.

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Azomethine imines react with alkenes and alkynes to give pyrazolines, pyrazolidines, pyrazolopyridines, indazoloisoquinolines, pyrazolo[1,5-a]isoquinolines and pyrazolopyrazolones through regio-, stereo- and enantioselective 1,3-dipolar cycloadditions.

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6

Wagner, Bernd, Wolf Hiller, Hiroaki Ohno, and Norbert Krause. "Gold-catalyzed three-component spirocyclization: a one-pot approach to functionalized pyrazolidines." Organic & Biomolecular Chemistry 14, no. 5 (2016): 1579–83. http://dx.doi.org/10.1039/c5ob02453f.

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7

Peng, Xiansha, Danfeng Huang, Ke-Hu Wang, et al. "Synthesis of trifluoromethylated pyrazolidines by [3 + 2] cycloaddition." Organic & Biomolecular Chemistry 15, no. 29 (2017): 6214–22. http://dx.doi.org/10.1039/c7ob01299c.

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[3 + 2] cycloaddition between trifluoromethylated N-acylhydrazones and nitroolefins in the presence of potassium hydroxide and Bu<sub>4</sub>NI is developed to afford potentially bioactive trifluoromethylated pyrazolidines.

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8

Davis, Lindsey O., William F. M. Daniel, and Suzanne L. Tobey. "Phosphonic acid catalyzed synthesis of pyrazolidines." Tetrahedron Letters 53, no. 5 (2012): 522–25. http://dx.doi.org/10.1016/j.tetlet.2011.11.083.

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9

Wen, Lan, Danfeng Huang, Ke-Hu Wang, et al. "[3+2] Cycloaddition of Trifluoromethylated N-Acylhydrazones with Maleates: Synthesis of Trifluoromethylated Pyrazolidines." Synthesis 50, no. 10 (2018): 1979–90. http://dx.doi.org/10.1055/s-0036-1591768.

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An efficient [3+2] cycloaddition reaction of trifluoromethylated N-acylhydrazones with dimethyl maleate has been developed under basic conditions. This protocol provides an easy access to potentially bioactive trifluoromethylated pyrazolidines in moderate to excellent yields. It also illustrates that the trifluoromethylated N-acylhydrazones are useful trifluoromethyl building blocks for the synthesis of trifluoromethylated N-heterocycles.

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10

Chaudhry, Faryal, Benson M. Kariuki, and David W. Knight. "A new method for the synthesis of pyrazolidines." Tetrahedron Letters 57, no. 26 (2016): 2833–37. http://dx.doi.org/10.1016/j.tetlet.2016.05.011.

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11

Davis, Lindsey O., William F. M. Daniel, and Suzanne L. Tobey. "ChemInform Abstract: Phosphonic Acid Catalyzed Synthesis of Pyrazolidines." ChemInform 43, no. 21 (2012): no. http://dx.doi.org/10.1002/chin.201221108.

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12

Petek, Nejc, Uroš Grošelj, Jurij Svete, Franc Požgan, Drago Kočar, and Bogdan Štefane. "Eosin Y-Catalyzed Visible-Light-Mediated Aerobic Transformation of Pyrazolidine-3-One Derivatives." Catalysts 10, no. 9 (2020): 981. http://dx.doi.org/10.3390/catal10090981.

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By utilizing an underexplored reactivity of N1-substituted pyrazolidine-3-ones, we developed a visible-light-induced aerobic oxidation of N1-substituted pyrazolidine-3-one derivatives yielding the corresponding azomethine imines. The resulting azomethine imines can be further reacted with ynones in situ under copper catalyzed [3 + 2] cycloaddition reaction conditions yielding the corresponding pyrazolo[1,2-a]pyrazoles in good yields. The methodology can be extended to other 1-aryl-substituted pyrazolidinones which undergo endocyclic oxidation deriving the corresponding pyrazolones as single pr

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13

Liu, Lili, Danfeng Huang, Yuxiang Wang, et al. "A Facile Synthesis of CF3-Substituted Pyrazolidines and Pyrazolines." Chinese Journal of Organic Chemistry 38, no. 6 (2018): 1469. http://dx.doi.org/10.6023/cjoc201712036.

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14

Yousfi, Tarek, Alysha Elliott, Messiad Hanane, Rachid Merdes, and Albert Moyano. "Expedient Organocatalytic Syntheses of 4-Substituted Pyrazolidines and Isoxazolidines." Molecules 21, no. 12 (2016): 1655. http://dx.doi.org/10.3390/molecules21121655.

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15

Usachev, Sergey V., Grygorii A. Nikiforov, Konstatin A. Lyssenko, Yulia V. Nelubina, Pavel A. Levkin, and Remir G. Kostyanovsky. "Sterically hindered and completely arrested nitrogen inversion in pyrazolidines." Tetrahedron: Asymmetry 18, no. 13 (2007): 1540–47. http://dx.doi.org/10.1016/j.tetasy.2007.06.022.

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16

Jakob, Florian, Eberhardt Herdtweck, and Thorsten Bach. "Synthesis and Properties of Chiral Pyrazolidines Derived from (+)-Pulegone." Chemistry - A European Journal 16, no. 25 (2010): 7537–46. http://dx.doi.org/10.1002/chem.201000219.

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17

Chauveau, A., T. Martens, M. Bonin, L. Micouin, and H. P. Husson. "Asymmetric Synthesis of Densely Functionalized Pyrazolidines and 1,3-Diamines." ChemInform 34, no. 1 (2003): no. http://dx.doi.org/10.1002/chin.200301116.

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18

Wagner, Bernd, Katrin Belger, Stefan Minkler, Volker Belting, and Norbert Krause. "Sustainable gold catalysis: synthesis of new spiroacetals." Pure and Applied Chemistry 88, no. 4 (2016): 391–99. http://dx.doi.org/10.1515/pac-2016-0406.

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AbstractVarious [O,O]- and [N,O]-spiroacetals were synthesized by gold-catalyzed spirocyclization of suitable functionalized alkynes. Whereas simple spiroacetals with two heteroatoms were readily obtained by regioselective cyclization of acetylenic diols or aminoalcohols, hitherto unknown spirocyclic isoxazolidines and pyrazolidines bearing three heteroatoms were formed by three-component coupling of alkynols, aldehydes, and protected hydroxylamine or hydrazine derivatives. The sustainability of these spirocyclizations was improved by using recyclable gold catalysts in water or nanomicelles as

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19

Vertesaljai, Peter, Iryna O. Lebedyeva, Alexander A. Oliferenko, et al. "Mimicking a proline tripeptide with pyrazolidines and a cyclopentane linker." Tetrahedron Letters 56, no. 48 (2015): 6653–55. http://dx.doi.org/10.1016/j.tetlet.2015.09.063.

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20

Katritzky, Alan R., Guofang Qiu, and Baozhen Yang. "Preparations of Trisubstituted Hydrazines and Pyrazolidines fromN-(1-Benzotriazolylalkyl)hydrazines." Journal of Organic Chemistry 62, no. 23 (1997): 8210–14. http://dx.doi.org/10.1021/jo9709110.

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21

LaLonde, R. L., Z. J. Wang, M. Mba, A. D. Lackner, and F. Dean Toste. "Gold(I)-Catalyzed Enantioselective Synthesis of Pyrazolidines, Isoxazolidines, and Tetrahydrooxazines." Angewandte Chemie International Edition 49, no. 3 (2009): 598–601. http://dx.doi.org/10.1002/anie.200905000.

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22

LaLonde, R. â L, Z. â J Wang, M. Mba, A. â D Lackner, and F. â Dean Toste. "Gold(I)-Catalyzed Enantioselective Synthesis of Pyrazolidines, Isoxazolidines, and Tetrahydrooxazines." Angewandte Chemie 122, no. 3 (2010): 608–11. http://dx.doi.org/10.1002/ange.200905000.

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23

Davis, Lindsey O. "Recent Developments in the Synthesis and Applications of Pyrazolidines. A Review." Organic Preparations and Procedures International 45, no. 6 (2013): 437–64. http://dx.doi.org/10.1080/00304948.2013.834769.

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24

Guerrand, Hélène D. S., Harry Adams, and Iain Coldham. "Cascade cyclization, dipolar cycloaddition of azomethine imines for the synthesis of pyrazolidines." Organic & Biomolecular Chemistry 9, no. 22 (2011): 7921. http://dx.doi.org/10.1039/c1ob06122d.

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25

Brugel, Todd A., Tomas Hudlicky, Michael P. Clark, et al. "Convergent synthesis of 2,3-bisarylpyrazolones through cyclization of bisacylated pyrazolidines and hydrazines." Tetrahedron Letters 47, no. 19 (2006): 3195–98. http://dx.doi.org/10.1016/j.tetlet.2006.03.063.

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26

LaLonde, R. L., Z. J. Wang, M. Mba, A. D. Lackner, and F. Dean Toste. "ChemInform Abstract: Gold(I)-Catalyzed Enantioselective Synthesis of Pyrazolidines, Isoxazolidines, and Tetrahydrooxazines." ChemInform 41, no. 21 (2010): no. http://dx.doi.org/10.1002/chin.201021031.

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27

Kalandarishvili, A. G., P. B. Terent'ev, S. V. Afanas'eva, et al. "Mass spectrometric study of ring-chain tautomers of 3-amino(hydroxy)pyrazolidines." Chemistry of Heterocyclic Compounds 22, no. 10 (1986): 1080–83. http://dx.doi.org/10.1007/bf00473482.

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28

KATRITZKY, A. R., G. QIU, and B. YANG. "ChemInform Abstract: Preparations of Trisubstituted Hydrazines and Pyrazolidines from N-(1-Benzotriazolylalkyl)hydrazines." ChemInform 29, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199817137.

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29

Davis, Lindsey O. "ChemInform Abstract: Recent Developments in the Synthesis and Applications of Pyrazolidines. A Review." ChemInform 45, no. 9 (2014): no. http://dx.doi.org/10.1002/chin.201409249.

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30

Bañuelos, Luis A., Purificación Cuadrado, Ana M. González-Nogal, Isabel López-Solera, Francisco J. Pulido, and Paul R. Raithby. "The reduction of functionalized pyrazolium salts as a stereoselective route to functionalized pyrazolidines." Tetrahedron 52, no. 27 (1996): 9193–206. http://dx.doi.org/10.1016/0040-4020(96)00470-x.

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31

Sviridova, L. A., G. A. Golubeva, A. N. Tavtorkin, and K. A. Kochetkov. "A new method for the synthesis of pyrazolidines with N-amino acid substitutents." Chemistry of Heterocyclic Compounds 44, no. 3 (2008): 368–69. http://dx.doi.org/10.1007/s10593-008-0055-z.

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32

Moldarev, B. L., M. E. Aronzon, V. M. Adanin, and A. M. Zyakun. "Chemistry of the pyrazolidines. 26. Alkylation of 4-benzyliden-1-phenyl-3.5-dioxopyrazolidines." Chemistry of Heterocyclic Compounds 22, no. 2 (1986): 176–80. http://dx.doi.org/10.1007/bf00519939.

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33

S. Ghabrial, Sami, Hussein H. Moharram, and Suzan I. Aziz. "Reactions with Maleimides: Synthesis of Several New Fused Pyrazolidines, D2-Pyrazoline and Pyrazole Derivatives." HETEROCYCLES 23, no. 5 (1985): 1161. http://dx.doi.org/10.3987/r-1985-05-1161.

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34

Požgan, Franc, Hamad Al Mamari, Uroš Grošelj, Jurij Svete, and Bogdan Štefane. "Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines." Molecules 23, no. 1 (2017): 3. http://dx.doi.org/10.3390/molecules23010003.

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35

Bahule, B. B. "Synthesis of Pyrazolidines (5-membered heterocyclic rings) through 1, 3- dipolar cycloadditions of azomethine imines." IOSR Journal of Applied Chemistry 2, no. 6 (2012): 39–40. http://dx.doi.org/10.9790/5736-0263940.

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36

BANUELOS, L. A., P. CUADRADO, A. M. GONZALEZ-NOGAL, I. LOPEZ-SOLERA, F. J. PULIDO, and P. R. RAITHBY. "ChemInform Abstract: The Reduction of Functionalized Pyrazolium Salts as a Stereoselective Route to Functionalized Pyrazolidines." ChemInform 27, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199645151.

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37

Tiecco, Marcello, Lorenzo Testaferri, and Francesca Marini. "Stereoselective organoselenium-induced cyclization of N-allyl acethydrazides to 1,3,4-oxadiazines or N-acetyl pyrazolidines." Tetrahedron 52, no. 36 (1996): 11841–48. http://dx.doi.org/10.1016/0040-4020(96)00675-8.

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38

Sviridova, Ludmila A., Galina A. Golubeva, Alexander N. Tavtorkin, and Konstantin A. Kochetkov. "Synthesis of hydroxydiamines and triamines via reductive cleavage of N–N bond in substituted pyrazolidines." Amino Acids 43, no. 3 (2012): 1225–31. http://dx.doi.org/10.1007/s00726-011-1187-5.

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39

Korotaev, Vladislav Yu, Igor B. Kutyashev, Vyacheslav Ya Sosnovskikh, and Mikhail I. Kodess. "Stereoselective synthesis of N-unsubstituted pyrazolidines from 3-nitro-2-trichloromethyl-2H-chromenes and hydrazine hydrate." Mendeleev Communications 17, no. 1 (2007): 52–53. http://dx.doi.org/10.1016/j.mencom.2007.01.021.

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40

TIECCO, M., L. TESTAFERRI, and F. MARINI. "ChemInform Abstract: Stereoselective Organoselenium-Induced Cyclization of N-Allyl Acethydrazides to 1,3,4-Oxadiazines or N-Acetyl Pyrazolidines." ChemInform 27, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199652185.

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41

Bañuelos, Luis A., Purificaciön Cuadrado, Ana M. González, and Francisco J. Pulido. "REDUCTION OF 3- AND/OR 5-UNSUBSTITUTED 2-ETHYLPYRAZOLIUM SALTS WITH COMPLEX METAL HYDRIDES. SYNTHESIS OF PYRAZOLIDINES." Organic Preparations and Procedures International 24, no. 2 (1992): 181–85. http://dx.doi.org/10.1080/00304949209355694.

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42

Sviridova, L. A., G. A. Golubeva, A. V. Mizgunov, I. V. Dlinnykh та V. N. Nesterov. "Interaction of 1-acetyl-2-phenyl-5-hydroxy-pyrazolidines withβ-substituted esters on the surface of adsorbents". Chemistry of Heterocyclic Compounds 33, № 4 (1997): 435–40. http://dx.doi.org/10.1007/bf02321388.

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43

S. B. Kalaskar, S. B. Kalaskar, B. B. Bahule B. B. Bahule, and Y. M. Nandurkar Y. M. Nandurkar. "A Novel One Pot Synthesis of Several 1(2,4 Dinitro Phenyl) – 3 Phenyl – 4 Methoxy Carbonyl Pyrazolidines Via 1,3 – Dipolar Cycloaddition Approach." International Journal of Scientific Research 3, no. 6 (2012): 70. http://dx.doi.org/10.15373/22778179/june2014/26.

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44

Cuadrado, Purificación, Ana M. González-Nogal, and Senén Martínez. "Reactions of pyrazoles and pyrazolium salts with complex metal hydrides and organometallic reagents. Synthesis of pyrazolines and pyrazolidines." Tetrahedron 53, no. 25 (1997): 8585–98. http://dx.doi.org/10.1016/s0040-4020(97)00514-0.

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45

de los Santos, Jesús M., Yago López, Domitila Aparicio, and Francisco Palacios. "A Convenient Synthesis of Substituted Pyrazolidines and Azaproline Derivatives through Highly Regio- and Diastereoselective Reduction of 2-Pyrazolines." Journal of Organic Chemistry 73, no. 2 (2008): 550–57. http://dx.doi.org/10.1021/jo702050t.

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46

Rueping, Magnus, Modhu Sudan Maji, Hatice Başpınar Küçük, and Iuliana Atodiresei. "Asymmetric Brønsted Acid Catalyzed Cycloadditions-Efficient Enantioselective Synthesis of Pyrazolidines, Pyrazolines, and 1,3-Diamines fromN-Acyl Hyrazones and Alkenes." Angewandte Chemie International Edition 51, no. 51 (2012): 12864–68. http://dx.doi.org/10.1002/anie.201205813.

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47

BANUELOS, L. A., P. CUADRADO, A. M. GONZALEZ, and F. J. PULIDO. "ChemInform Abstract: Reduction of 3- and/or 5-Unsubstituted 2-Ethylpyrazolium Salts with Complex Metal Hydrides. Synthesis of Pyrazolidines." ChemInform 23, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199236154.

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48

Kostyuchenko, I. V., E. V. Shulishov, V. A. Korolev, V. A. Dokichev, and Yu V. Tomilov. "Reduction of substituted spiro[cyclopropane-3-(1-pyrazolines)] to spiro[cyclopropane-3-pyrazolidines] and 1-(2-aminoethyl)cyclopropylamine derivatives." Russian Chemical Bulletin 54, no. 11 (2005): 2562–70. http://dx.doi.org/10.1007/s11172-006-0156-8.

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49

CUADRADO, P., A. M. GONZALEZ-NOGAL, and S. MARTINEZ. "ChemInform Abstract: Reactions of Pyrazoles and Pyrazolium Salts with Complex Metal Hydrides and Organometallic Reagents. Synthesis of Pyrazolines and Pyrazolidines." ChemInform 28, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199743136.

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50

Guerra, F. M., M. R. Mish, and E. M. Carreira. "Versatile, Diastereoselective Additions of Silyl Ketene Acetals, Allyl Tributylstannane, and Me3SiCN toN-Acyl Pyrazolines: Asymmetric Synthesis of Densely Functionalized Pyrazolidines." Organic Letters 2, no. 26 (2000): 4265–67. http://dx.doi.org/10.1021/ol006873f.

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