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Journal articles on the topic 'Azetidine synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

Sun, Jian, Shan Shan Gong, and Qi Sun. "A Novel Strategy for the Synthesis of Azetidine." Advanced Materials Research 830 (October 2013): 135–38. http://dx.doi.org/10.4028/www.scientific.net/amr.830.135.

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A novel method for the synthesis of azetidine via phosphoramidate intermediate has been developed. In the key step, cleavage of the PN bond in azetidin-1-ylphosporamidate with hydrochloric acid furnished a high-yielding conversion to azetidine hydrochloride.

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2

Nitta, Yoshihiro, and Yasuyuki Kanamori. "Synthesis of Azetidine from 1-Substituted Azetidin-3-ols." HETEROCYCLES 24, no. 9 (1986): 2467. http://dx.doi.org/10.3987/r-1986-09-2467.

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3

Peipiņš, Vilnis, Krista Suta, and Māris Turks. "Study on Synthesis of N-Protected 2-Triazolyl Azetidines." Key Engineering Materials 762 (February 2018): 19–24. http://dx.doi.org/10.4028/www.scientific.net/kem.762.19.

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Azetidine derivatives are interesting scaffolds in terms of medicinal chemistry. They can be regarded as structural homologs of aziridines. Herein we report synthetic approach to the novel N-protected 2-triazolyl azetidines which are structurally similar to our previously described aziridine derivatives with matrix metalloproteinase-2 inhihbitory activities. The synthetic rout includes ring closing of ethyl 2,4-dibromobutanoate, selective reduction of ester to aldehyde and transformation of the latter to terminal alkyne by Ohira-Bestmann reagent. 2-Ethynyl azetidines as key intermediates were

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4

Duréault, Annie, Martine Portal, François Carreaux, and Jean Claude Depezay. "Synthesis of highly functionalized homochiral azetidines and azetidine-2-carboxylic esters." Tetrahedron 49, no. 20 (1993): 4201–10. http://dx.doi.org/10.1016/s0040-4020(01)85738-0.

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5

Tayama, Eiji, та Nobuhiro Nakanome. "Synthesis of optically active 2-substituted azetidine-2-carbonitriles from chiral 1-arylethylamine via α-alkylation of N-borane complexes". RSC Advances 11, № 38 (2021): 23825–37. http://dx.doi.org/10.1039/d1ra04585g.

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6

Jin, Jian Zhong, and Jie Zhang. "Synthesis of L-Azetidine-2-Carboxylic Acid." Advanced Materials Research 455-456 (January 2012): 635–38. http://dx.doi.org/10.4028/www.scientific.net/amr.455-456.635.

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L-Azetidine-2-carboxylic acid, the first known example naturally occurring azetidine, was synthesized in a novel, simple, clean and improved procedure. It was synthesized from γ-butyrolactone through four steps: bromination and esterification, cyclization, hydrogenation and resolution. The overall yield could reach 13.2%.

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7

Hanessian, Stephen, and Jian-min Fu. "Total synthesis of polyoximic acid." Canadian Journal of Chemistry 79, no. 11 (2001): 1812–26. http://dx.doi.org/10.1139/v01-171.

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The structure and stereochemistry of polyoximic acid, a degradation product of polyoxins, was originally designated as trans-3-ethylidene-L-azetidine-2-carboxylic acid. However, total synthesis revealed that the correct structure was in fact cis-3-ethylidene-L-azetidine-2-carboxylic acid, which was confirmed by X-ray crystallography. The synthesis of the trans-isomer was also done and its identity was confirmed by X-ray analysis as well. The key step for constructing the four-membered ring was a rhodium catalyzed carbenoid insertion into the NH bond of a beta-amino acid derivative. The stereo

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8

Reidl, Tyler W., Jongwoo Son, Donald J. Wink, and Laura L. Anderson. "Facile Synthesis of Azetidine Nitrones and Diastereoselective Conversion into Densely Substituted Azetidines." Angewandte Chemie International Edition 56, no. 38 (2017): 11579–83. http://dx.doi.org/10.1002/anie.201705681.

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9

Reidl, Tyler W., Jongwoo Son, Donald J. Wink, and Laura L. Anderson. "Facile Synthesis of Azetidine Nitrones and Diastereoselective Conversion into Densely Substituted Azetidines." Angewandte Chemie 129, no. 38 (2017): 11737–41. http://dx.doi.org/10.1002/ange.201705681.

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10

Gavale, Kishor S., Shrawan R. Chavan, Ayesha Khan, Rakesh Joshi, and Dilip D. Dhavale. "Azetidine- and N-carboxylic azetidine-iminosugars as amyloglucosidase inhibitors: synthesis, glycosidase inhibitory activity and molecular docking studies." Organic & Biomolecular Chemistry 13, no. 23 (2015): 6634–46. http://dx.doi.org/10.1039/c5ob00668f.

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11

Fenoglio, Ivana, Gian Mario Nano, David G. Vander Velde, and Giovanni Appendino. "Synthesis of azetidine-type taxanes." Tetrahedron Letters 37, no. 18 (1996): 3203–6. http://dx.doi.org/10.1016/0040-4039(96)00495-9.

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12

Causey, David H., Richard P. Mays, Dwight A. Shamblee, and Young S. Lo. "A Practical Synthesis of Azetidine." Synthetic Communications 18, no. 2 (1988): 205–11. http://dx.doi.org/10.1080/00397918808077346.

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13

Rao, G. "A Novel Diazomethane-Mediated Synthesis of Azetidine-Embedded Tetracyclic Ketal Systems." Synthesis 50, no. 10 (2018): 2094–98. http://dx.doi.org/10.1055/s-0037-1609363.

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Herein, the first diazomethane-mediated synthesis of azetidine-embedded tetracyclic ketal systems is reported. Reactions of norbornyl hemiaminal acetals with diazomethane afford azetidine-embedded tetracyclic ketals in good to excellent yields. The bridgehead-bromo-substituted hemiaminal acetals give higher yields compared to the corresponding bridgehead-chloro-substituted hemiaminal acetals. The hemiaminal acetals are prepared stereoselectively via nucleophilic addition of various amines to norbornyl α-diketones from the exo face.

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14

DUREAULT, A., M. PORTAL, F. CARREAUX, and J. C. DEPEZAY. "ChemInform Abstract: Synthesis of Highly Functionalized Homochiral Azetidines and Azetidine- 2-carboxylic Esters." ChemInform 24, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199339168.

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15

Hamill, Rosalie, Benjamin Jones, Christopher M. Pask, and Visuvanathar Sridharan. "Synthesis of oxetane/azetidine containing spirocycles." Tetrahedron Letters 60, no. 16 (2019): 1126–29. http://dx.doi.org/10.1016/j.tetlet.2019.03.042.

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16

Barrett, Anthony G. M., Paola Dozzo, Andrew J. P. White, and David J. Williams. "Synthesis of chiral bicyclic azetidine derivatives." Tetrahedron 58, no. 36 (2002): 7303–13. http://dx.doi.org/10.1016/s0040-4020(02)00761-5.

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17

Yakura, Takayuki, and Tomoya Fujiwara. "Synthesis of Sphingosine-Related Azetidine Alkaloids, Penaresidins: Construction of Highly Substituted Azetidine Rings." HETEROCYCLES 101, no. 2 (2020): 383. http://dx.doi.org/10.3987/rev-19-sr(f)3.

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18

Sajjadi, Z., and W. D. Lubell. "Amino acid-azetidine chimeras: synthesis of enantiopure 3-substituted azetidine-2-carboxylic acids." Journal of Peptide Research 65, no. 2 (2008): 298–310. http://dx.doi.org/10.1111/j.1399-3011.2005.00228.x.

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19

Burtoloso, Antonio Carlos B., and Carlos Roque D. Correia. "Stereoselective synthesis of azetidine-derived glutamate and aspartate analogues from chiral azetidin-3-ones." Tetrahedron 64, no. 42 (2008): 9928–36. http://dx.doi.org/10.1016/j.tet.2008.08.001.

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20

Gleede, Tassilo, Louis Reisman, Elisabeth Rieger, Pierre Canisius Mbarushimana, Paul A. Rupar, and Frederik R. Wurm. "Aziridines and azetidines: building blocks for polyamines by anionic and cationic ring-opening polymerization." Polymer Chemistry 10, no. 24 (2019): 3257–83. http://dx.doi.org/10.1039/c9py00278b.

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21

Ding, Feiqing, Ronny William, Si Min Kock, Min Li Leow, and Xue-Wei Liu. "A concise route to the highly-functionalized azetidine precursor: the enantioselective synthesis of penaresidin B." Chemical Communications 51, no. 22 (2015): 4639–42. http://dx.doi.org/10.1039/c4cc09904d.

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22

Nassoy, Anne-Chloé M. A., Piotr Raubo, and Joseph P. A. Harrity. "Synthesis and indole coupling reactions of azetidine and oxetane sulfinate salts." Chemical Communications 51, no. 27 (2015): 5914–16. http://dx.doi.org/10.1039/c5cc00975h.

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23

Bacqué, Eric, Jean-Marc Paris, and Séverine Le Bitoux. "Synthesis of 3-Amino 3-Phenyl Azetidine." Synthetic Communications 25, no. 6 (1995): 803–12. http://dx.doi.org/10.1080/00397919508013416.

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24

Bari, S. S., I. R. Trehan, A. K. Sharma, and M. S. Manhas. "A Facile Synthesis of Azetidine-2,4-diones." Synthesis 1992, no. 05 (1992): 439–42. http://dx.doi.org/10.1055/s-1992-26128.

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25

Rupanwar, Bapurao D., Santosh S. Chavan, Anil M. Shelke, and Gurunath M. Suryavanshi. "Triflic acid-catalyzed metal-free synthesis of (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones." New Journal of Chemistry 42, no. 8 (2018): 6433–40. http://dx.doi.org/10.1039/c7nj05169g.

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26

Zhou, Genlai, Jingwen Su, Tianbo Shang, et al. "Synthesis of polysubstituted azetidines via cascade trifluoromethylation/cyclization of N-allyl ynamides." Organic Chemistry Frontiers 8, no. 16 (2021): 4473–78. http://dx.doi.org/10.1039/d1qo00559f.

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27

Tayama, Eiji, Ryotaro Nishio та Yoshiaki Kobayashi. "Base-promoted diastereoselective α-alkylation of borane N-((S)-1′-phenylethyl)azetidine-2-carboxylic acid ester complexes". Organic & Biomolecular Chemistry 16, № 32 (2018): 5833–45. http://dx.doi.org/10.1039/c8ob01395k.

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Synthesis of optically-active α-substituted azetidine-2-carboxylic acid esters starting from (S)-1-phenylethylamine was successfully demonstrated via diastereoselective N-boration followed by α-alkylation.

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28

Devi, K. Shashikala, M. Ramaiah, D. L. Roopa, and V. P. Vaidya. "Synthesis and Investigation of Antimicrobial and Antioxidant Activity of 3-Nitro-N- (3-chloro-2-oxo-substituted-phenyl-azetidin-1-yl)naphtho [2,1-b]furan-2-carboxamides." E-Journal of Chemistry 7, s1 (2010): S358—S362. http://dx.doi.org/10.1155/2010/863547.

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Ethyl-3-nitronaphtho[2,1-b]furan-2-carboxylate(2)has been synthesized from ethyl naphtha [2,1-b]furan-2-carboxylate(1). This nitro product on reaction with hydrazine hydrate formed 3-nitronaphtho [2,1-b] furan-2-carbohydrazide(3). Various Schiff bases 3-nitro-N1(aryl-methylene)-substituted-naphtho [2,1-b]furan-2-carbohydrazides4(a-g)were obtained by treating hydrazide(3)with different aldehydes. These Schiff bases on reaction with chloro acetyl chloride in presence of triethylamine in dioxane yielded 3-nitro-N-(3-chloro-2-oxo-substituted-phenyl-azetidine-1-yl) naphtha [2,1-b]furan-2-carboxamid

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29

Shimokawa, Jun, Takaaki Harada, Satoshi Yokoshima, and Tohru Fukuyama. "Total synthesis of gelsemoxonine." Pure and Applied Chemistry 84, no. 7 (2012): 1643–50. http://dx.doi.org/10.1351/pac-con-11-10-25.

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The first total synthesis of gelsemoxonine has been accomplished. A divinylcyclopropane–cycloheptadiene rearrangement of the highly functionalized substrate successfully assembled the spiro-quaternary carbon center connected to the bicyclic seven-membered core structure. A one-pot isomerization reaction of the α,β-unsaturated aldehyde to the saturated ester via a trimethylsilyl cyanide–diazabicycloundecene (TMSCN–DBU) reagent combination allowed a facile and diastereoselective introduction of the latent nitrogen functionality in the unique azetidine moiety.

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30

Wang, Brian J., and Matthew A. J. Duncton. "A Single-Step Synthesis of Azetidine-3-amines." Journal of Organic Chemistry 85, no. 20 (2020): 13317–23. http://dx.doi.org/10.1021/acs.joc.0c01831.

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31

Andresini, Michael, Sonia De Angelis, Antonella Uricchio, et al. "Azetidine–Borane Complexes: Synthesis, Reactivity, and Stereoselective Functionalization." Journal of Organic Chemistry 83, no. 17 (2018): 10221–30. http://dx.doi.org/10.1021/acs.joc.8b01441.

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32

O′Neil, Ian A., and Andrew J. Potter. "Simple azetidine N-oxides: synthesis, structure and reactivity." Chemical Communications, no. 14 (1998): 1487–88. http://dx.doi.org/10.1039/a802503g.

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33

Arakawa, Yasushi, Tomoaki Murakami, Yukimi Arakawa, and Shigeyuki Yoshifuji. "Stereospecific Synthesis of Azetidine-cis-2,3-dicarboxylic Acid." CHEMICAL & PHARMACEUTICAL BULLETIN 51, no. 1 (2003): 96–97. http://dx.doi.org/10.1248/cpb.51.96.

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34

Laguerre, Michel, Chantal Boyer, Jean-Michel Leger, and Alain Carpy. "New investigations of the reaction of epichlorohydrin with hindered amines: X-ray and NMR analyses." Canadian Journal of Chemistry 67, no. 10 (1989): 1514–22. http://dx.doi.org/10.1139/v89-232.

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During the synthesis of a series of new antiarhythmic drugs, the reaction between epichlorohydrin and hindered amines was reinvestigated. With primary amines, 3-azetidinols were formed in fair yields. The X-ray structure elucidation of one of these compounds (1: P21/n, a = 17.210, b = 6.665, c = 23.585, β = 102.29, and R = 0.064 for 2005 observed reflections) and NMR studies led to the conclusion that both the hydroxy group and the bulky nitrogen substituent are on the same side of the azetidine ring. With secondary amines, the reaction was very complex, leading to diamino dioxane, diamino alc

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35

Chavan, Santosh S., Mrudul V. Supekar, Pralhad A. Burate, Bapurao D. Rupanwar, Anil M. Shelke, and Gurunath Suryavanshi. "An efficient Sn(ii)-catalyzed one-pot synthesis of a 3-substituted azetidine-2,4-dione framework." Organic & Biomolecular Chemistry 15, no. 11 (2017): 2385–91. http://dx.doi.org/10.1039/c7ob00294g.

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A novel Sn(ii)-catalyzed tandem cyclization reaction of aromatic aldehydes with ethyl cyanoacetate has been achieved to afford a series of 3-substituted azetidine-2,4-diones in good to excellent yields.

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36

Harrowfield, Jack M., Gyu Hwan Jang, Yang Kim, Pierre Thuéry, and Jacques Vicens. "Azetidines as intermediates in polyamine synthesis – structure and reactions of a quadridentate ligand incorporating an azetidine ring." Journal of the Chemical Society, Dalton Transactions, no. 7 (February 27, 2002): 1241–43. http://dx.doi.org/10.1039/b200382a.

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37

Vázquez, Miguel, Fernando Hernández-Borja, Leticia Contreras, et al. "Synthesis of Novel Hybrid 4H-Pyran-lipoic and 4H-Pyran-azetidine Derivatives." Synthesis 50, no. 05 (2017): 1020–26. http://dx.doi.org/10.1055/s-0036-1591730.

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In this study, a molecular hybridization strategy was used to design and synthesize two novel series of hybrid compounds: 4H-pyran-lipoic and 4H-pyran-azetidine, employing ammonium hydroxide and involving the participation of aldehydes, malononitrile, and compounds derived from β-ketoesters to obtain the products with good yields.

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38

Nagao, Yoshimitsu, Kazuhiko Hayashi, Shinsuke Hiki, and Toshio Kumagai. "Synthesis of Azetidine Derivatives Using 1-Azabicyclo[1.1.0]butane." HETEROCYCLES 56, no. 1-2 (2002): 433. http://dx.doi.org/10.3987/com-01-s(k)65.

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39

Jin, Jian Zhong, and Jie Zhang. "Synthesis of L-Azetidine-2-Carboxylic Acid." Advanced Materials Research 455-456 (January 2012): 635–38. http://dx.doi.org/10.4028/scientific5/amr.455-456.635.

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40

Biswas, Tanmoy, Jyoti Prasad Mukherjee, and Shital K. Chattopadhyay. "Enantiodivergent synthesis of N-protected azetidine-2-carboxylic acid." Tetrahedron: Asymmetry 23, no. 18-19 (2012): 1416–22. http://dx.doi.org/10.1016/j.tetasy.2012.08.016.

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41

Agami, Claude, François Couty, and Nicolas Rabasso. "An efficient asymmetric synthesis of azetidine 2-phosphonic acids." Tetrahedron Letters 43, no. 26 (2002): 4633–36. http://dx.doi.org/10.1016/s0040-4039(02)00868-7.

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42

Knapp, Spencer, and Yaohua Dong. "Stereoselective synthesis of penaresidin A and related azetidine alkaloids." Tetrahedron Letters 38, no. 22 (1997): 3813–16. http://dx.doi.org/10.1016/s0040-4039(97)00753-3.

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43

Kharul, Rajendra K., Amitgiri Goswami, Archana Gite, Atul K. Godha, Mukul Jain, and Pankaj R. Patel. "Convenient Synthesis of Structurally Novel 1,3‐Disubstituted Azetidine Derivatives." Synthetic Communications 38, no. 11 (2008): 1703–17. http://dx.doi.org/10.1080/00397910801982340.

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44

Upadhyay, Apoorva, S. K. Srivastava, and S. D. Srivastava. "Synthesis and Characterization of New 2-Oxo-azetidine Derivatives." Synthetic Communications 41, no. 17 (2011): 2544–56. http://dx.doi.org/10.1080/00397911.2010.515328.

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45

BACQUE, E., J. M. PARIS, and S. LE BITOUX. "ChemInform Abstract: Synthesis of 3-Amino-3-phenyl-azetidine." ChemInform 26, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199527146.

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46

BARI, S. S., I. R. TREHAN, A. K. SHARMA, and M. S. MANHAS. "ChemInform Abstract: A Facile Synthesis of Azetidine-2,4-diones." ChemInform 23, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199236171.

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47

Yadav, Lal Dhar S., Vishnu P. Srivastava, and Rajesh Patel. "The first application of the Baylis–Hillman reaction in azetidine chemistry: a convenient synthesis of azetidine-3-carbonitriles/carboxylates." Tetrahedron Letters 49, no. 39 (2008): 5652–54. http://dx.doi.org/10.1016/j.tetlet.2008.07.069.

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48

Yoda, Hidemi, Masaki Takahashi, and Tetsuya Sengoku. "ChemInform Abstract: Azetidine and Its Derivatives in Natural Product Synthesis." ChemInform 43, no. 2 (2011): no. http://dx.doi.org/10.1002/chin.201202220.

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49

O'NEIL, I. A., and A. J. POTTER. "ChemInform Abstract: Simple Azetidine N-Oxides: Synthesis, Structure and Reactivity." ChemInform 29, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199843116.

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50

Van Brabandt, Willem, Yves Dejaegher та Norbert De Kimpe. "New reactions of functionalized β-lactams". Pure and Applied Chemistry 77, № 12 (2005): 2061–71. http://dx.doi.org/10.1351/pac200577122061.

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An easy synthesis of 4-(1- and 2-haloalkyl)azetidin-2-ones by a [2+2] cycloadditon protocol is described. Starting from these functionalized β-lactams, new pathways toward bicyclic β-lactams were developed via intramolecular nucleophilic substitutions and radical cyclizations. 4-(1- and 2-Haloalkyl)azetidin-2-ones also proved to be very useful starting products in the synthesis of various highly substituted aziridines, azetidines, and alkenoates.

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