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Journal articles on the topic 'Oxazinanes'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Van Nguyen, Tuyen, Matthias D’hooghe, Hang Dao Thi, Giang Le Nhat Thuy, Saron Catak, and Veronique Van Speybroeck. "Use of 3-Hydroxy-4-(trifluoromethyl)azetidin-2-ones as Building Blocks for the Preparation of Trifluoromethyl-Containing Aminopropanes, 1,3-Oxazinan-2-ones, Aziridines, and 1,4-Dioxan-2-ones." Synthesis 50, no. 07 (2018): 1439–56. http://dx.doi.org/10.1055/s-0036-1591537.

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3-Hydroxy-4-(trifluoromethyl)azetidin-2-ones were synthesized from the corresponding 3-benzyloxy-β-lactams and successfully transformed into new 3-chloro-4-(trifluoromethyl)azetidin-2-one building blocks. The latter chlorides were shown to be eligible precursors for the construction of CF3-containing aminopropanes, 1,3-oxazinanes, 1,3-oxazinan-2-ones, and aziridines. In addition, 3-hydroxy-4-(trifluoromethyl)azetidin-2-ones proved to be interesting substrates for the synthesis of novel 3-[2,2,2-trifluoro-1-(arylamino)ethyl]-1,4-dioxan-2-ones via intramolecular cyclization of 3-(2-hydroxyethoxy

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2

Chandgude, Ajay L., Daniele Narducci, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, and Alexander Dömling. "Diastereoselective one pot five-component reaction toward 4-(tetrazole)-1,3-oxazinanes." RSC Adv. 7, no. 79 (2017): 49995–98. http://dx.doi.org/10.1039/c7ra07392e.

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3

Hardman, Andrea M., Sonia S. So, and Anita E. Mattson. "Urea-catalyzed construction of oxazinanes." Organic & Biomolecular Chemistry 11, no. 35 (2013): 5793. http://dx.doi.org/10.1039/c3ob41517a.

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4

Cheng, Shuanghua, and Shouyun Yu. "Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition." Org. Biomol. Chem. 12, no. 43 (2014): 8607–10. http://dx.doi.org/10.1039/c4ob01646g.

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A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er).

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5

Zhai, Pingan, Wenhui Li, Jianying Lin, Shuangping Huang, Wenchao Gao, and Xing Li. "N-Alkyl nitrones as substrates for access to N-aryl isoxazolidines via a catalyst-free one-pot three-component reaction with nitroso compounds and olefins." Organic Chemistry Frontiers 8, no. 14 (2021): 3752–59. http://dx.doi.org/10.1039/d1qo00398d.

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N-Alkyl nitrones are used as starting materials to construct N-aryl isoxazolidines, instead of N-alkyl isoxazolidines or N–H 1,3-oxazinanes via a catalyst-free one-pot three-component reaction with nitrosoarenes and olefins.

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6

Vukićević, Rastko, Matthias D’hooghe, Anka Pejović, et al. "Synthesis and Antimicrobial/Cytotoxic Assessment of Ferrocenyl Oxazinanes, Oxazinan-2-ones, and Tetrahydropyrimidin-2-ones." Synlett 26, no. 09 (2015): 1195–200. http://dx.doi.org/10.1055/s-0034-1380348.

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7

Hardman, Andrea M., Sonia S. So, and Anita E. Mattson. "ChemInform Abstract: Urea-Catalyzed Construction of Oxazinanes." ChemInform 45, no. 2 (2013): no. http://dx.doi.org/10.1002/chin.201402172.

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8

Zanatta, Nilo, Adriana M. C. Squizani, Leonardo Fantinel, et al. "Synthesis of N-substituted 6-trifluoromethyl-1,3-oxazinanes." Journal of the Brazilian Chemical Society 16, no. 6a (2005): 1255–61. http://dx.doi.org/10.1590/s0103-50532005000700025.

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9

Van Nguyen, Tuyen, Matthias D’hooghe, Hang Dao Thi та ін. "Synthesis of Trifluoromethylated Azetidines, Aminopropanes, 1,3-Oxazinanes, and 1,3-Oxazinan-2-ones Starting from 4-Trifluoromethyl-β-lactam Building Blocks". Synlett 27, № 07 (2016): 1100–1105. http://dx.doi.org/10.1055/s-0035-1561316.

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10

Singh, Kamajit, and Prasant K. Deb. "A Versatile Approach to trans-1,3-Disubstituted Tetrahydro-b-carbolines Using Oxazinanes." HETEROCYCLES 51, no. 7 (1999): 1509. http://dx.doi.org/10.3987/com-99-8580.

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11

Cordier, Marie, and Alexis Archambeau. "(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes." Organic Letters 20, no. 8 (2018): 2265–68. http://dx.doi.org/10.1021/acs.orglett.8b00617.

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12

Nimmagadda, Sri Krishna, Zuhui Zhang, and Jon C. Antilla. "Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and 1,3-Oxazinanes via Hemiaminal Intermediates." Organic Letters 16, no. 16 (2014): 4098–101. http://dx.doi.org/10.1021/ol501789c.

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13

Ramakrishna, Isai, Panduga Ramaraju, and Mahiuddin Baidya. "Synthesis of Chiral 1,2-Oxazinanes and Isoxazolidines via Nitroso Aldol Reaction of Distal Dialdehydes." Organic Letters 20, no. 4 (2018): 1023–26. http://dx.doi.org/10.1021/acs.orglett.7b03968.

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14

Singh, Kamajit, та Prasant K. Deb. "ChemInform Abstract: A Versatile Approach to trans-1,3-Disubstituted Tetrahydro-β-carbolines Using Oxazinanes." ChemInform 30, № 42 (2010): no. http://dx.doi.org/10.1002/chin.199942159.

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15

Cheng, Shuanghua, and Shouyun Yu. "ChemInform Abstract: Enantioselective Synthesis of 3-Substituted 1,2-Oxazinanes via Organocatalytic Intramolecular Aza-Michael Addition." ChemInform 46, no. 13 (2015): no. http://dx.doi.org/10.1002/chin.201513254.

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16

Nimmagadda, Sri Krishna, Zuhui Zhang, and Jon C. Antilla. "ChemInform Abstract: Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and 1,3-Oxazinanes via Hemiaminal Intermediates." ChemInform 46, no. 7 (2015): no. http://dx.doi.org/10.1002/chin.201507025.

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17

Artemov, A. N., E. V. Sazonova, N. A. Aksenova, et al. "Reaction of phenyl-containing N-substituted 1,3-oxazolidines and 1,3-oxazinanes with triammine(tricarbonyl)chromium." Russian Chemical Bulletin 68, no. 8 (2019): 1548–54. http://dx.doi.org/10.1007/s11172-019-2590-4.

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18

Al-Masum, Mohammad, Baillie W. Lott, and Nazanin Ghazialsharif. "An Efficient Reaction Process for the Synthesis of Oxazinanes, and Oxazolidines in the Presence of Air." International Journal of Organic Chemistry 02, no. 04 (2012): 362–65. http://dx.doi.org/10.4236/ijoc.2012.24049.

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19

Singh, Kamaljit, Sonia Behal та Prasant K. Deb. "2-(Arylsulfinylmethyl)oxazinanes: chiral carbonyl equivalents. Application to the asymmetric synthesis of 1,2,3,4-tetrahydro-β-carbolines". Tetrahedron 60, № 41 (2004): 9171–77. http://dx.doi.org/10.1016/j.tet.2004.07.062.

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20

Hu, Lingbowei, Michael Rombola, and Viresh H. Rawal. "Synthesis of 1,2-Oxazinanes via Hydrogen Bond Mediated [3 + 3] Cycloaddition Reactions of Oxyallyl Cations with Nitrones." Organic Letters 20, no. 17 (2018): 5384–88. http://dx.doi.org/10.1021/acs.orglett.8b02301.

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21

Hu, Junhao, Min Zhang, and Yuefa Gong. "Cycloaddition Reactions of Alkyl Cyclopropenecarboxylates Generated in situ with Nitrones: Construction of Substituted Pyrroles and 1,2-Oxazinanes." European Journal of Organic Chemistry 2015, no. 9 (2015): 1970–78. http://dx.doi.org/10.1002/ejoc.201403551.

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22

Alberola, Angel, Maria A. Alvarez, Celia Andrés, Alfonso González та Rafael Pedrosa. "Nucleophilic Ring Opening of 3-Benzyl-1,3-oxazinanes by Reformatsky Reagents. A Synthesis of β-Amino Ester Derivatives". Synthesis 1990, № 11 (1990): 1057–58. http://dx.doi.org/10.1055/s-1990-27092.

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23

Ni, Yang, Honghua Zuo, Huaibin Yu, Yuzhou Wu, and Fangrui Zhong. "Synergistic Catalysis-Enabled Thia-Aza-Prins Cyclization with DMSO and Disulfides: Entry to Sulfenylated 1,3-Oxazinanes and Oxazolidines." Organic Letters 20, no. 18 (2018): 5899–904. http://dx.doi.org/10.1021/acs.orglett.8b02551.

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24

Lin, Weilong, Ke-Feng Zhang та Olivier Baudoin. "Regiodivergent enantioselective C–H functionalization of Boc-1,3-oxazinanes for the synthesis of β2- and β3-amino acids". Nature Catalysis 2, № 10 (2019): 882–88. http://dx.doi.org/10.1038/s41929-019-0336-1.

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25

Hashmi, Syed M. A., Mohammed I. M. Wazeer, M. Sakhawat Hussain, Joseph H. Reibenspies, Herman P. Perzanowski, and Sk Asrof Ali. "Conformational assignments and a nitrogen inversion process in some 3-acyloxy-1,3-oxazinanes by NMR and X-ray analysis." Journal of the Chemical Society, Perkin Transactions 2, no. 4 (1999): 877–84. http://dx.doi.org/10.1039/a807273f.

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26

Singh, Kamaljit, Jasbir Singh, and Harjit Singh. "A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles." Tetrahedron 52, no. 45 (1996): 14273–80. http://dx.doi.org/10.1016/0040-4020(96)00879-4.

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27

Hu, Junhao, Min Zhang, and Yuefa Gong. "ChemInform Abstract: Cycloaddition Reactions of Alkyl Cyclopropenecarboxylates Generated in situ with Nitrones: Construction of Substituted Pyrroles and 1,2-Oxazinanes." ChemInform 46, no. 31 (2015): no. http://dx.doi.org/10.1002/chin.201531034.

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28

ALBEROLA, A., M. A. ALVAREZ, C. ANDRES, A. GONZALEZ та R. PEDROSA. "ChemInform Abstract: Nucleophilic Ring Opening of 3-Benzyl-1,3-oxazinanes by Reformatsky Reagents. A Synthesis of β-Amino Ester Derivatives." ChemInform 22, № 22 (2010): no. http://dx.doi.org/10.1002/chin.199122096.

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29

D’hooghe, Matthias, Stijn Dekeukeleire, Karen Mollet, et al. "Synthesis of Novel 2-Alkoxy-3-amino-3-arylpropan-1-ols and 5-Alkoxy-4-aryl-1,3-oxazinanes with Antimalarial Activity." Journal of Medicinal Chemistry 52, no. 13 (2009): 4058–62. http://dx.doi.org/10.1021/jm9002632.

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30

SINGH, K., J. SINGH, and H. SINGH. "ChemInform Abstract: A Synthetic Entry into Fused Pyran Derivatives Through Carbon Transfer Reactions of 1,3-Oxazinanes and Oxazolidines with Carbon Nucleophiles." ChemInform 28, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.199710044.

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31

Artemov, A. N., E. V. Sazonova, N. A. Krylova та ін. "The synthesis of new 1,3-oxazolidines and 1,3-oxazinanes containing (η6-arene)tricarbonylchromium group based on condensation between aldehydes and amino alcohols". Russian Chemical Bulletin 67, № 5 (2018): 884–92. http://dx.doi.org/10.1007/s11172-018-2153-0.

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32

Yao, Chuan-Zhi, Zu-Feng Xiao, Jie Liu, Xiao-Shan Ning, and Yan-Biao Kang. "Ru-Catalyzed Rearrangement of N-Methyl Isoxazolidines to N–H 1,3-Oxazinanes: A Strategy of Self-Hydride Transferring Cleavage of N–O Bonds." Organic Letters 16, no. 9 (2014): 2498–501. http://dx.doi.org/10.1021/ol500869p.

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33

Huang, Xiu-Rong, Yu-Mei Zhang, Ting-Biao Wan, et al. "Straightforward synthesis of 4,5-bifunctionalized 1,2-oxazinanes via Lewis acid promoted regio- and stereo-selective nucleophilic ring-opening of 3,6-dihydro-1,2-oxazine oxides." Tetrahedron 75, no. 45 (2019): 130336. http://dx.doi.org/10.1016/j.tet.2019.05.015.

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34

Yao, Chuan-Zhi, Zu-Feng Xiao, Jie Liu, Xiao-Shan Ning, and Yan-Biao Kang. "ChemInform Abstract: Ru-Catalyzed Rearrangement of N-Methyl Isoxazolidines to N-H 1,3-Oxazinanes: A Strategy of Self-Hydride Transferring Cleavage of N-O Bonds." ChemInform 45, no. 46 (2014): no. http://dx.doi.org/10.1002/chin.201446193.

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35

GOOSEN, A., C. W. MCCLELAND, and A. M. SIPAMLA. "ChemInform Abstract: Reactions of N-Benzyl- and N-Benzylidene-alkanolamines with Bromine: Formation of 1,3-Oxazolidines, 1,3-Oxazinanes, 4,5-Dihydro-1,3- oxazoles and 5,6-Dihydro-4H-1,3-oxazines." ChemInform 27, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199607070.

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36

Ghorai, Manas K., Kalpataru Das, and Amit Kumar. "Lewis acid mediated SN2-type nucleophilic ring opening followed by [4+2] cycloaddition of N-tosylazetidines with aldehydes and ketones: synthesis of chiral 1,3-oxazinanes and 1,3-amino alcohols." Tetrahedron Letters 48, no. 25 (2007): 4373–77. http://dx.doi.org/10.1016/j.tetlet.2007.04.097.

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37

Tsipis, Constantinos A., Evangelos G. Bakalbassis, Stavroula A. Zisopoulou, and John K. Gallos. "Probing the anomeric effect and mechanism of isomerization of oxazinane rings by DFT methods." Organic & Biomolecular Chemistry 19, no. 5 (2021): 1066–82. http://dx.doi.org/10.1039/d0ob02453h.

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38

Aricò, Fabio, Sara Bravo, Marco Crisma, and Pietro Tundo. "1,3-Oxazinan-2-ones via carbonate chemistry: a facile, high yielding synthetic approach." Pure and Applied Chemistry 88, no. 3 (2016): 227–37. http://dx.doi.org/10.1515/pac-2015-1004.

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AbstractA high yielding synthesis of 1,3-oxazinan-2-ones starting from 3-amino-1-propanols and ethylene carbonate (EC) in the presence of catalytic amount of triazabicyclodecene (TBD) is herein reported. The formation of six-membered cyclic carbonates was achieved by intermolecular cyclization reaction via double BAc2 mechanism. Cyclization reactions have been carried out in neat as EC acted both as solvent and reagent. Pure 1,3-oxazinan-2-ones were isolated in high yield by simple liquid-liquid extraction. Further purification can be achieved by recrystallization. The reaction resulted of gen

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39

Alcaide, Benito, Pedro Almendros, M. Teresa Quirós, and Israel Fernández. "Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones." Beilstein Journal of Organic Chemistry 9 (April 26, 2013): 818–26. http://dx.doi.org/10.3762/bjoc.9.93.

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A combined experimental and computational study on regioselective gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out.

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40

Wang, Weilin, Yixin Fu, Yimeng Li, et al. "Ag(i)-Catalyzed solvent-free CO2 capture with homopropargylic amines: an efficient access to 1,3-oxazinan-2-ones." Organic Chemistry Frontiers 5, no. 22 (2018): 3331–35. http://dx.doi.org/10.1039/c8qo00978c.

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An efficient solvent-free CO<sub>2</sub> capture and transformation method was developed through using homopropargylic amines in the presence of AgOAc and DBU, and a series of 1,3-oxazinan-2-ones was obtained in excellent yields.

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41

Yang, Bin, Kantapat Chansaenpak, Hongmiao Wu, et al. "Silver-promoted (radio)fluorination of unsaturated carbamates via a radical process." Chemical Communications 53, no. 24 (2017): 3497–500. http://dx.doi.org/10.1039/c7cc01393k.

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The intramolecular fluorocyclization of unsaturated carbamates proceeds via a cyclization/1,2-(hetero)aryl migration/fluorination cascade involving an unusual radical process, and provides a straightforward access to (radio)fluorinated oxazolidin-2-ones, oxazolidine-2,4-diones and 1,3-oxazinan-2-ones.

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42

Hughes, Andrew B., та Brad E. Sleebs. "Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt - Eistert Procedure". Australian Journal of Chemistry 58, № 11 (2005): 778. http://dx.doi.org/10.1071/ch05199.

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N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl α-amino acid, which was then homologated via an Arndt–Eistert procedure in high yield to give the N-methyl β-amino acid.

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43

Journal, Baghdad Science. "Synthesis & Characterization of Oxazinan and 5-oxa-7-aza-spiro[2,5] octane from reaction of Dibenzylidene with malonic anhydride and 5-oxa-spiro[2,3] hexane-4,6-dione." Baghdad Science Journal 4, no. 2 (2007): 276–84. http://dx.doi.org/10.21123/bsj.4.2.276-284.

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Di Benzylidenes were prepared by condensation of 1,2-diamino benzene with o- hydroxy benzaldehyde. These dibenzylidenes when treated with one equivalent of malonic anhydride or 5-oxo-spiro[2,3]hexane-4,6-dione in dry benzene give 6-membered heterocyclic ring system of 3-{2-[(2-Hydroxy-benzylidene)-amino]-phenyl}-2-(2-hydroxy –phenyl)-[1,3]oxazinane-4,6-diones ( 1-3) or 7-{2-[(2-hydroxy-benzylidene)-amino]-phenyl}-6-(2-hydroxy-phenyl)-5-oxa-7-aza-spiro[2.5]octane-4,8-diones ( 7- 9 ) But when two equivalents of malonic anhydride or 5-oxo-spiro[2,3]hexane-4,6-dione were used and under sam conditi

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44

Zong, Kyukwan, Seung Il Shin, Hyung Ki Kim, Hyoung Rae Kim, Dong Ju Jeon, and Eung K. Ryu. "ChemInform Abstract: A Facile Synthesis of [1,2]Oxazinane-3,5-diones." ChemInform 31, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.200008188.

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45

Djigoue, Guy-Bertrand, Michel Simard, Lucie-Carolle Kenmogne, and Donald Poirier. "Two androsterone derivatives as inhibitors of androgen biosynthesis." Acta Crystallographica Section C Crystal Structure Communications 68, no. 6 (2012): o231—o234. http://dx.doi.org/10.1107/s0108270112021099.

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The title compounds, (3R,5S,5′R,8R,9S,10S,13S,14S)-10,13-dimethyl-5′-(2-methylpropyl)tetradecahydro-6′H-spiro[cyclopenta[a]phenanthrene-3,2′-[1,4]oxazinane]-6′,17(2H)-dione, C26H41NO3, (I), and methyl (2R)-2-[(3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2′,17-dioxohexadecahydro-3′H-spiro[cyclopenta[a]phenanthrene-3,5′-[1,3]oxazolidin-3′-yl]]-4-methylpentanoate, C28H43NO5, (II), possess the typical steroid shape (A–Drings), but they differ in their extraEring. The azalactoneEring in (I) shows a half-chair conformation, while the carbamateEring of (II) is planar. The orientation of theE-ring substit

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46

Wang, Guijun. "Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones." Anti-Infective Agents in Medicinal Chemistry 7, no. 1 (2008): 32–49. http://dx.doi.org/10.2174/187152108783329771.

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47

Mino, Takashi, Sosuke Hata, Kouji Ohtaka, Masami Sakamoto, and Tsutomu Fujita. "Novel chiral phosphine–oxazinane ligands in palladium-catalyzed asymmetric allylic alkylation." Tetrahedron Letters 42, no. 29 (2001): 4837–39. http://dx.doi.org/10.1016/s0040-4039(01)00860-7.

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48

Cui, Shi-Sheng, Rong Huang, Da-Yun Luo, Sheng-Jiao Yan, and Jun Lin. "Selective Synthesis of Highly Functionalized Bicyclic Pyridinone and 1,3-Oxazinane Derivatives." European Journal of Organic Chemistry 2017, no. 24 (2017): 3442–50. http://dx.doi.org/10.1002/ejoc.201700283.

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49

Khankischpur, Mehdi, Rolf D. Walter, and Thomas Kurz. "Synthesis and Antiplasmodial Activity of 4-Alkylidene(arylidene)hydrazono-1,3-oxazinan-2-ones and 3-Hydroxy-N'-alkylidene(arylidene)propanehydrazonamides." Australian Journal of Chemistry 63, no. 10 (2010): 1430. http://dx.doi.org/10.1071/ch10052.

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Previously unreported 6-substituted 4-alkylidene(arylidene)hydrazono-1,3-oxazinan-2-ones and a series of open-chained 3-hydroxy-N′-alkylidene(arylidene)propanehydrazonamides were synthesized and evaluated for their in vitro antiplasmodial activity. The most active 3-hydroxy-N′-alkylidene(arylidene)propanehydrazonamide exhibits potent in vitro antiplasmodial activity against the chloroquine-sensitive strain 3D7 of Plasmodium falciparum and demonstrates an IC50 value of 0.2 µM.

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50

Wang, Chao, and Jon A. Tunge. "Decarboxylative Ring Contractions and Olefin Insertions of Vinyl Oxazinanones." Organic Letters 8, no. 15 (2006): 3211–14. http://dx.doi.org/10.1021/ol0610744.

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