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Artigos de revistas sobre o tema "Azetines"

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Autor: Grafiati

Publicado: 7 de julho de 2024

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1

Baumann, Andreas N., Michael Eisold, Arif Music, Geoffrey Haas, Yu Min Kiw e Dorian Didier. "Methods for the Synthesis of Substituted Azetines". Organic Letters 19, n.º 20 (4 de outubro de 2017): 5681–84. http://dx.doi.org/10.1021/acs.orglett.7b02847.

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2

Hodgson, David M., Christopher I. Pearson e Madiha Kazmi. "Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines". Organic Letters 16, n.º 3 (10 de janeiro de 2014): 856–59. http://dx.doi.org/10.1021/ol403626k.

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3

Hodgson, David M., Christopher I. Pearson e Madiha Kazmi. "ChemInform Abstract: Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines." ChemInform 45, n.º 29 (3 de julho de 2014): no. http://dx.doi.org/10.1002/chin.201429118.

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4

Didier, Dorian, e Felix Reiners. "Uncommon Four‐Membered Building Blocks – Cyclobutenes, Azetines and Thietes". Chemical Record 21, n.º 5 (18 de março de 2021): 1144–60. http://dx.doi.org/10.1002/tcr.202100011.

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5

Baumann, Andreas N., Michael Eisold, Arif Music, Geoffrey Haas, Yu Min Kiw e Dorian Didier. "Correction to Methods for the Synthesis of Substituted Azetines". Organic Letters 19, n.º 24 (22 de novembro de 2017): 6763. http://dx.doi.org/10.1021/acs.orglett.7b03520.

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6

Dejaegher, Yves, Sven Mangelinckx e Norbert De Kimpe. "Rearrangement of 2-Aryl-3,3-dichloroazetidines: Intermediacy of 2-Azetines". Journal of Organic Chemistry 67, n.º 7 (abril de 2002): 2075–81. http://dx.doi.org/10.1021/jo010914j.

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7

Marichev, Kostiantyn O., Kan Wang, Kuiyong Dong, Nicole Greco, Lynée A. Massey, Yongming Deng, Hadi Arman e Michael P. Doyle. "Synthesis of Chiral Tetrasubstituted Azetidines from Donor–Acceptor Azetines via Asymmetric Copper(I)‐Catalyzed Imido‐Ylide [3+1]‐Cycloaddition with Metallo‐Enolcarbenes". Angewandte Chemie International Edition 58, n.º 45 (24 de setembro de 2019): 16188–92. http://dx.doi.org/10.1002/anie.201909929.

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8

Marichev, Kostiantyn O., Kan Wang, Kuiyong Dong, Nicole Greco, Lynée A. Massey, Yongming Deng, Hadi Arman e Michael P. Doyle. "Synthesis of Chiral Tetrasubstituted Azetidines from Donor–Acceptor Azetines via Asymmetric Copper(I)‐Catalyzed Imido‐Ylide [3+1]‐Cycloaddition with Metallo‐Enolcarbenes". Angewandte Chemie 131, n.º 45 (24 de setembro de 2019): 16334–38. http://dx.doi.org/10.1002/ange.201909929.

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9

Dejaegher, Yves, Sven Mangelinckx e Norbert De Kimpe. "ChemInform Abstract: Rearrangement of 2-Aryl-3,3-dichloroazetidines: Intermediacy of 2-Azetines." ChemInform 33, n.º 36 (20 de maio de 2010): no. http://dx.doi.org/10.1002/chin.200236110.

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10

MacNevin, Christopher J., Rhonda L. Moore e Dennis C. Liotta. "Stereoselective Synthesis of Quaternary Center Bearing Azetines and Their β-Amino Acid Derivatives". Journal of Organic Chemistry 73, n.º 4 (fevereiro de 2008): 1264–69. http://dx.doi.org/10.1021/jo7018202.

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11

Hemming, Karl, Musharraf N. Khan, Paul A. O'Gorman e Arnaud Pitard. "1,2,4-Oxadiazoles from cycloreversions of oxadiazabicyclo[3.2.0]heptenes: 1-azetines as thiocyanate equivalents". Tetrahedron 69, n.º 4 (janeiro de 2013): 1279–84. http://dx.doi.org/10.1016/j.tet.2012.12.007.

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12

Luheshi, Abdul-Basset N., Robert K. Smalley, P. D. Kennewell e R. Westwood. "1,3-Dipolar cycloadditions of 2-ethoxy- and 2-(ethylthio)-1-azetines with nitrilimines". Tetrahedron Letters 31, n.º 1 (janeiro de 1990): 127–30. http://dx.doi.org/10.1016/s0040-4039(00)94352-1.

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13

Giubellina, Nicola, Wim Aelterman e Norbert De Kimpe. "Use of 3-halo-1-azaallylic anions in heterocyclic chemistry". Pure and Applied Chemistry 75, n.º 10 (1 de janeiro de 2003): 1433–42. http://dx.doi.org/10.1351/pac200375101433.

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The synthetic potential of lithio 3-halo-1-azaallylic anions as building blocks in organic chemistry and especially in heterocyclic chemistry will be highlighted by the synthesis of functionalized imines, obtained after reaction of 3-halo-1-azaallylic anions with het- eroatom-substituted electrophiles. Thus, the latter generated functionalized imines are suitable building blocks for the synthesis of a whole range of heterocycles and physiologically active compounds, including agrochemicals and pharmaceuticals. 3-Halo-1-azaallylic anions were used in the synthesis of N-alkyl-3,3-dichloroazetidines, 2,3-disubstituted pyrroles, piperidines, 2-substituted pyridines, 2-alkoxytetrahydrofurans,etc., from which a large range of useful and interesting chemicals can be produced, e.g., 2-azetines and 9-alkyl- 2-phenyl-3a-beta,4,6,7,8,9,9a-beta,9b-beta-octahydro-1H-pyrrolo [3,4,h]quinoline-1,3-diones. The utility of the present methodology is demonstrated by the synthesis of the pheromone (S)-manicone, the sulfur-containing flavor compound 2-[(methylthio)methyl ]-2-butenal, and some agrochemical and pharmaceutical compounds.

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14

Hara, Shunya, e Shigekazu Ito. "TiCl 4 ‐Mediated [2+2] Cycloaddition for Synthesis of Isolable CF 3 ‐Substituted 2‐Azetines". Asian Journal of Organic Chemistry 10, n.º 4 (17 de março de 2021): 788–92. http://dx.doi.org/10.1002/ajoc.202100082.

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15

Lopez, Steven A., e K. N. Houk. "Substituent Effects on Rates and Torquoselectivities of Electrocyclic Ring-Openings of N-Substituted 2-Azetines". Journal of Organic Chemistry 79, n.º 13 (12 de junho de 2014): 6189–95. http://dx.doi.org/10.1021/jo500919s.

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16

Mangelinckx, Sven, Veronique Van Speybroeck, Peter Vansteenkiste, Michel Waroquier e Norbert De Kimpe. "Experimental and Computational Study of the Conrotatory Ring Opening of Various 3-Chloro-2-azetines". Journal of Organic Chemistry 73, n.º 14 (julho de 2008): 5481–88. http://dx.doi.org/10.1021/jo800522b.

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17

Barluenga, José, Lorena Riesgo, Giacomo Lonzi, Miguel Tomás e Luis A. López. "Copper(I)-Catalyzed [3+1] Cycloaddition of Alkenyldiazoacetates and Iminoiodinanes: Easy Access to Substituted 2-Azetines". Chemistry - A European Journal 18, n.º 30 (21 de junho de 2012): 9221–24. http://dx.doi.org/10.1002/chem.201200998.

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18

Santos, Bruna S., Ana L. Cardoso, Ana Matos Beja, Manuela Ramos Silva, José A. Paixão, Francisco Palacios e Teresa M. V. D. Pinho e Melo. "Diastereoselective Aza-Baylis-Hillman Reactions: Synthesis of Chiral α-Allenylamines and 2-Azetines from Allenic Esters". European Journal of Organic Chemistry 2010, n.º 17 (30 de abril de 2010): 3249–56. http://dx.doi.org/10.1002/ejoc.200901415.

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19

Singh, Atul K., Ruchi Chawla e Lal Dhar S. Yadav. "Retracted article: Convenient access to strained trisubstituted 2-azetines from enals and chloramine-T in aqueous media". Green Chemistry 14, n.º 12 (2012): 3325. http://dx.doi.org/10.1039/c2gc36331c.

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20

Luheshi, Abdul-Basset N., Robert K. Smalley, Peter D. Kennewell e Robert Westwood. "1,3-Dipolar cycloadditions of 2-ethoxy- and 2-(ethylthio)-1-azetines with nitrile oxides and nitrile ylides". Tetrahedron Letters 31, n.º 1 (janeiro de 1990): 123–26. http://dx.doi.org/10.1016/s0040-4039(00)94351-x.

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21

Singh, Atul K., Ruchi Chawla e Lal Dhar S. Yadav. "ChemInform Abstract: Convenient Access to Strained Trisubstituted 2-Azetines from Enals and Chloramine-T in Aqueous Media." ChemInform 44, n.º 15 (25 de março de 2013): no. http://dx.doi.org/10.1002/chin.201315087.

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22

Santos, Bruna S., Ana L. Cardoso, Ana Matos Beja, Manuela Ramos Silva, Jose A. Paixao, Francisco Palacios e Teresa M. V. D. Pinho e Melo. "ChemInform Abstract: Diastereoselective Aza-Baylis-Hillman Reactions: Synthesis of Chiral α-Allenylamines and 2-Azetines from Allenic Esters." ChemInform 41, n.º 44 (7 de outubro de 2010): no. http://dx.doi.org/10.1002/chin.201044029.

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23

Barluenga, Jose, Lorena Riesgo, Giacomo Lonzi, Miguel Tomas e Luis A. Lopez. "ChemInform Abstract: Copper(I)-Catalyzed [3 + 1] Cycloaddition of Alkenyldiazoacetates and Iminoiodinanes: Easy Access to Substituted 2-Azetines." ChemInform 43, n.º 50 (29 de novembro de 2012): no. http://dx.doi.org/10.1002/chin.201250101.

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24

Funes-Ardoiz, Ignacio, Jairo González, Javier Santamaría e Diego Sampedro. "Understanding the Mechanism of the Divergent Reactivity of Non-Heteroatom-Stabilized Chromium Carbene Complexes with Furfural Imines: Formation of Benzofurans and Azetines". Journal of Organic Chemistry 81, n.º 4 (4 de fevereiro de 2016): 1565–70. http://dx.doi.org/10.1021/acs.joc.5b02729.

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25

Shindoh, Naoya, Kazuo Kitaura, Yoshiji Takemoto e Kiyosei Takasu. "Catalyst-Controlled Torquoselectivity Switch in the 4π Ring-Opening Reaction of 2-Amino-2-azetines Giving β-Substituted α,β-Unsaturated Amidines". Journal of the American Chemical Society 133, n.º 22 (8 de junho de 2011): 8470–73. http://dx.doi.org/10.1021/ja202576e.

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26

Marchand, Alan P., D. Rajagopal, Simon G. Bott e Thomas G. Archibald. "Reactions of 1-ethyl-3-azabicyclo[1.1.0]butane with electrophiles. A facile entry into new, N-substituted 3-ethylideneazetidines and 2-azetines". Journal of Organic Chemistry 59, n.º 7 (abril de 1994): 1608–12. http://dx.doi.org/10.1021/jo00086a008.

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27

Hemming, Karl, Paul A. O’Gorman e Michael I. Page. "The synthesis of azabicyclo[4.2.1]nonenes by the addition of a cyclopropenone to 4-vinyl substituted 1-azetines—isomers of the homotropane nucleus". Tetrahedron Letters 47, n.º 4 (janeiro de 2006): 425–28. http://dx.doi.org/10.1016/j.tetlet.2005.11.081.

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28

Hemming, Karl, Abdul-Bassett N. Luheshi, Alan D. Redhouse, Robert K. Smalley, J. Robin Thompson, Peter D. Kennewell e R. Westwood. "1,3-dipolar cycloadditions of 2-Ethoxy- and 2-(ethylthio)-1-azetines with nitrile oxides, nitrile ylides and nitrilimines: An unexpected 1,2,4-triazole formation." Tetrahedron 49, n.º 20 (janeiro de 1993): 4383–408. http://dx.doi.org/10.1016/s0040-4020(01)85755-0.

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29

Jung, Michael E., e Yong Mi Choi. "New synthesis of 2-azetines and 1-azabutadienes and the use of the latter in Diels-Alder reactions: total synthesis of (.+-.)-.delta.-coniceine". Journal of Organic Chemistry 56, n.º 24 (novembro de 1991): 6729–30. http://dx.doi.org/10.1021/jo00024a001.

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30

MARCHAND, A. P., D. RAJAGOPAL, S. G. BOTT e T. G. ARCHIBALD. "ChemInform Abstract: Reactions of 1-Aza-3-ethylbicyclo(1.1.0)butane with Electrophiles. A Facile Entry into New, N-Substituted 3-Ethylideneazetidines and 2- Azetines." ChemInform 25, n.º 36 (19 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199436134.

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31

JUNG, M. E., e Y. M. CHOI. "ChemInform Abstract: New Synthesis of 2-Azetines and 1-Azabutadienes and the Use of the Latter in Diels-Alder Reactions: Total Synthesis of (.+-.)-δ- Coniceine." ChemInform 23, n.º 18 (22 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199218169.

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32

HEMMING, K., A. B. N. LUHESHI, A. D. REDHOUSE, R. K. SMALLEY, J. R. THOMPSON, P. D. KENNEWELL e R. WESTWOOD. "ChemInform Abstract: 1,3-Dipolar Cycloadditions of 2-Ethoxy- and 2-(Ethylthio)-1-azetines with Nitrile Oxides, Nitrile Ylides and Nitrilimines: An Unexpected 1, 2,4-Triazole Formation." ChemInform 24, n.º 39 (20 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199339086.

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33

Yan, Hao, Xincheng Li, Chunxiang Wang e Boshun Wan. "Silver-catalyzed cyclization of nitrones with 2-azetine: a radical approach to 2,3-disubstituted quinolines". Organic Chemistry Frontiers 4, n.º 9 (2017): 1833–38. http://dx.doi.org/10.1039/c7qo00405b.

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34

Mughal, Haseeb, e Michal Szostak. "Recent advances in the synthesis and reactivity of azetidines: strain-driven character of the four-membered heterocycle". Organic & Biomolecular Chemistry 19, n.º 15 (2021): 3274–86. http://dx.doi.org/10.1039/d1ob00061f.

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Azetidines represent one of the most important four-membered heterocycles in organic synthesis. We provide an overview of the synthesis, reactivity and application of azetidines with a focus on the most recent advances, trends and future directions.

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35

Reidl, Tyler W., e Laura L. Anderson. "Divergent Functionalizations of Azetidines and Unsaturated Azetidines". Asian Journal of Organic Chemistry 8, n.º 7 (3 de junho de 2019): 931–45. http://dx.doi.org/10.1002/ajoc.201900229.

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36

Brianna Barbu. "Azetidines, assemble!" C&EN Global Enterprise 102, n.º 20 (1 de julho de 2024): 5. http://dx.doi.org/10.1021/cen-10220-scicon7.

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37

Mehra, Vishu, Isha Lumb, Amit Anand e Vipan Kumar. "Recent advances in synthetic facets of immensely reactive azetidines". RSC Adv. 7, n.º 72 (2017): 45763–83. http://dx.doi.org/10.1039/c7ra08884a.

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38

Peipiņš, Vilnis, Krista Suta e Māris Turks. "Study on Synthesis of N-Protected 2-Triazolyl Azetidines". Key Engineering Materials 762 (fevereiro de 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 transformed into triazole derivatives by Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction.

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39

Fawcett, Alexander. "Recent advances in the chemistry of bicyclo- and 1-azabicyclo[1.1.0]butanes". Pure and Applied Chemistry 92, n.º 5 (26 de maio de 2020): 751–65. http://dx.doi.org/10.1515/pac-2019-1007.

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AbstractBicyclo[1.1.0]- and 1-azabicyclo[1.1.0]butanes are structurally unique compounds that exhibit diverse chemistry. Bicyclo[1.1.0]butane is a four-membered carbocycle with a bridging C(1)-C(3) bond and 1-azabicyclo[1.1.0]butane is an analog of bicyclo[1.1.0]butane featuring a nitrogen atom at one bridgehead. These structures are highly strained, allowing them to participate in a range of strain-releasing reactions which typically cleave the central, strained bond to deliver cyclobutanes or azetidines. However, despite these molecules being discovered in the 1950s and 1960s, and possessing a myriad of alluring chemical features, the chemistry and applications of bicyclo[1.1.0]- and 1-azabicyclo[1.1.0]butanes remain underexplored. In the past 5 years, there has been a resurgent interest in their chemistry driven by the pharmaceutical industry’s increasing desire for new methods to access cyclobutanes and azetidines. This short review intends to provide a timely summary of the most recent developments in the chemistry of bicyclo[1.1.0]- and 1-azabicyclo[1.1.0]butane to highlight the diverse chemistry they can access, their value as synthetic precursors to cyclobutanes and azetidines, and to identify areas for future research.

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40

Ghorai, Manas K., Subhomoy Das, Kalpataru Das e Amit Kumar. "Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction". Organic & Biomolecular Chemistry 13, n.º 34 (2015): 9042–49. http://dx.doi.org/10.1039/c5ob01140j.

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41

Musci, Pantaleo, Marco Colella, Angela Altomare, Giuseppe Romanazzi, Nadeem S. Sheikh, Leonardo Degennaro e Renzo Luisi. "Dynamic Phenomena and Complexation Effects in the α-Lithiation and Asymmetric Functionalization of Azetidines". Molecules 27, n.º 9 (29 de abril de 2022): 2847. http://dx.doi.org/10.3390/molecules27092847.

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In this work it is demonstrated that enantiomerically enriched N-alkyl 2-oxazolinylazetidines undergo exclusive α-lithiation, and that the resulting lithiated intermediate is chemically stable but configurationally labile under the given experimental conditions that afford enantioenriched N-alkyl-2,2-disubstituted azetidines. Although this study reveals the configurational instability of the diastereomeric lithiated azetidines, it points out an interesting stereoconvergence of such lithiated intermediates towards the thermodynamically stable species, making the overall process highly stereoselective (er > 95:5, dr > 85:15) after trapping with electrophiles. This peculiar behavior has been rationalized by considering the dynamics at the azetidine nitrogen atom, the inversion at the C-Li center supported by in situ FT-IR experiments, and DFT calculations that suggested the presence of η3-coordinated species for diastereomeric lithiated azetidines. The described situation contrasted with the demonstrated stability of the smaller lithiated aziridine analogue. The capability of oxazolinylazetidines to undergo different reaction patterns with organolithium bases supports the model termed “dynamic control of reactivity” of relevance in organolithium chemistry. It has been demonstrated that only 2,2-substituted oxazolinylazetidines with suitable stereochemical requirements could undergo C=N addition of organolithiums in non-coordinating solvents, leading to useful precursors of chiral (er > 95:5) ketoazetidines.

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42

Vinayak, Sumiti, Rajiv S. Jumani, Peter Miller, Muhammad M. Hasan, Briana I. McLeod, Jayesh Tandel, Erin E. Stebbins et al. "Bicyclic azetidines kill the diarrheal pathogen Cryptosporidium in mice by inhibiting parasite phenylalanyl-tRNA synthetase". Science Translational Medicine 12, n.º 563 (30 de setembro de 2020): eaba8412. http://dx.doi.org/10.1126/scitranslmed.aba8412.

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Cryptosporidium is a protozoan parasite and a leading cause of diarrheal disease and mortality in young children. Currently, there are no fully effective treatments available to cure infection with this diarrheal pathogen. In this study, we report a broad drug repositioning effort that led to the identification of bicyclic azetidines as a new anticryptosporidial series. Members of this series blocked growth in in vitro culture of three Cryptosporidium parvum isolates with EC50’s in 1% serum of <0.4 to 96 nM, had comparable potencies against Cryptosporidium hominis and C. parvum, and was effective in three of four highly susceptible immunosuppressed mice with once-daily dosing administered for 4 days beginning 2 weeks after infection. Comprehensive genetic, biochemical, and chemical studies demonstrated inhibition of C. parvum phenylalanyl-tRNA synthetase (CpPheRS) as the mode of action of this new lead series. Introduction of mutations directly into the C. parvum pheRS gene by CRISPR-Cas9 genome editing resulted in parasites showing high degrees of compound resistance. In vitro, bicyclic azetidines potently inhibited the aminoacylation activity of recombinant ChPheRS. Medicinal chemistry optimization led to the identification of an optimal pharmacokinetic/pharmacodynamic profile for this series. Collectively, these data demonstrate that bicyclic azetidines are a promising series for anticryptosporidial drug development and establish a broad framework to enable target-based drug discovery for this infectious disease.

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43

Roy, Tony, Sachin Suresh Bhojgude, Trinadh Kaicharla, Manikandan Thangaraj, Bikash Garai e Akkattu T. Biju. "Employing carboxylic acids in aryne multicomponent coupling triggered by aziridines/azetidines". Organic Chemistry Frontiers 3, n.º 1 (2016): 71–76. http://dx.doi.org/10.1039/c5qo00328h.

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The transition-metal-free aryne multicomponent coupling (MCC) involving carboxylic acids initiated by aziridines/azetidines leading to the synthesis of N-aryl β/γ-amino alcohol derivatives has been developed.

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44

Parmar, Dixit, Lena Henkel, Josef Dib e Magnus Rueping. "Iron catalysed cross-couplings of azetidines – application to the formal synthesis of a pharmacologically active molecule". Chemical Communications 51, n.º 11 (2015): 2111–13. http://dx.doi.org/10.1039/c4cc09337b.

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A protocol for the cross-coupling of azetidines with aryl, heteroaryl, vinyl and alkyl Grignard reagents has been developed under iron catalysis. In addition, a short formal synthesis of a pharmacologically active molecule was demonstrated.

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45

Gomathy, Subramanian. "MOLECULAR DOCKING STUDIES, IN SILICO ADMET SCREENING OF SELECTED NOVEL AZETIDINE SUBSTITUTED NAPHTHALENE’S TARGETING PROTEASE ENZYME AGAINST SARS COV-19". Journal of Medical pharmaceutical and allied sciences 10, n.º 6 (15 de novembro de 2021): 3986–91. http://dx.doi.org/10.22270/jmpas.v10i6.2505.

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The emergence and dissemination of SARS COVID-19 has resulted in a high death rate, necessitating a large-scale search for viable antiSARS COVID-19 therapeutics. The binding mechanisms of 25 azetidines bearing naphthalene derivatives as Anti-SARS COVID-19 inhibitors, targeting protease enzyme via molecular docking, ADME and Toxicity Prediction (TOPKAT) investigations were investigated in this work, and they were compared to the FDA-approved medicine remdesivir. Compounds 22, 18, 17, 14 had the highest Lib Dock score among the 25 derivatives, with the X-ray crystallographic structure of M pro (PDB ID: 6LU7) revealing important interactions with residues Glu166, Gln192, Ala191, Thr190, Ser144, Cys145. These findings imply that these azetidine derivatives may be useful in the development of more effective anti-SARS COVID-19 agents. Keywords: Main protease enzyme, SARS COVID-19, Azetidines, Naphthalenes, In-silicoscreening

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Andresini, Michael, Leonardo Degennaro e Renzo Luisi. "The renaissance of strained 1-azabicyclo[1.1.0]butanes as useful reagents for the synthesis of functionalized azetidines". Organic & Biomolecular Chemistry 18, n.º 30 (2020): 5798–810. http://dx.doi.org/10.1039/d0ob01251c.

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Since their discovery in the late 1960s, 1-azabicyclo[1.1.0]butanes have demonstrated to be interesting precursors of azetidines, because of the peculiar reactivity of the C3–N bond that allows double functionalization in the 1,3 positions.

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Dave, Paritosh R., Rajagopal Duddu, Rao Surapaneni e Richard Gilardi. "Diels-Alder reactions ofN-acetyl-2-azetine". Tetrahedron Letters 40, n.º 3 (janeiro de 1999): 443–46. http://dx.doi.org/10.1016/s0040-4039(98)02506-4.

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Crunkhorn, Sarah. "Bicyclic azetidines treat cryptosporidiosis". Nature Reviews Drug Discovery 19, n.º 12 (2 de novembro de 2020): 838. http://dx.doi.org/10.1038/d41573-020-00193-y.

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Christmann, M., R. de Figueiredo e R. Fröhlich. "Synthesis of Chiral Azetidines". Synfacts 2006, n.º 9 (setembro de 2006): 0879. http://dx.doi.org/10.1055/s-2006-942066.

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Antermite, Daniele, Leonardo Degennaro e Renzo Luisi. "Recent advances in the chemistry of metallated azetidines". Organic & Biomolecular Chemistry 15, n.º 1 (2017): 34–50. http://dx.doi.org/10.1039/c6ob01665k.

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The almost unexplored four-membered azetidines represent a particularly interesting class of molecules, among the family of saturated nitrogen heterocycles. This review reports recent developments in direct metal-based functionalization of the azetidine ring, focusing on the regio- and stereoselectivity of these reactions.

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