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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 1
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ARTICLE

One-pot synthesis of novel ether-linked diisoxazole derivatives via sequential O-propargylation and 1,3-dipolar cycloaddition from 2-bromohomoallylic alcohols

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Pages 97-103 | Received 26 Mar 2019, Published online: 07 Nov 2019

References

  • (a) Dömling, A. Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry. Chem. Rev. 2006, 106, 17-89. DOI: 10.1021/cr0505728. (b) Ganem, B. Strategies for Innovation in Multicomponent Reaction Design. Acc. Chem. Res. 2009, 42, 463-472. (c) Ali, R.; Ali, R. K. Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Applications. Curr. Org. Chem 2011, 15, 3986-4020. (d) Dömling, A.; Wang, W.; Wang, K. Chemistry and Biology of Multicomponent Reactions. Chem. Rev. 2012, 112, 3083-3135.
  • (a) Shiri, M. Indoles in Multicomponent Processes (MCPs). Chem. Rev. 2012, 112, 3508-3549. DOI: 10.1021/cr2003954. (b) Wu, X.-F.; Neumann, H.; Beller, M. Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations. Chem. Rev. 2013, 113, 1-35. (c) Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Small Heterocycles in Multicomponent Reactions. Chem. Rev. 2014, 114, 8323-8359. (d) Neochoritis, C. G.; Zhao, T.; Dömling, A. Tetrazoles via Multicomponent Reactions. Chem. Rev. 2019, 119, 1970-2042. (e) Zahra, H.; Ali, R.; Nima, R.-A. Anti-Cancer Nitrogen-Containing Heterocyclic Compounds. Curr. Org. Chem 2018, 22, 2256-2279.
  • (a) Sheng, W.-S.; Sheng, S.-R.; Zeng, J.-B.; Huang, Z.-Z.; Cai, M.-Z. Four-Component, One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles Bearing 1-(2-Phenylselenocyclohexyl) Group. J. Heterocyclic Chem 2014, 51, E222-E226. (b) Potuganti, G. R.; Indukuri, D. R.; Nanubolu, J. B.; Alla, M. Copper-Catalyzed Domino Addition, Hydroamination, and Cyclization: A Multicomponent Approach to Spiro Oxazolidinone Derivatives. J. Org. Chem 2018, 83, 15186-15194. (c) Aghahosseini, H.; Ramazani, A.; Jalayer, N. S.; Ranjdoost, Z.; Souldozi, A.; Ślepokura, K.; Lis, T. Vinylphosphonium Salt-Mediated Reactions: A One-Pot Condensation Approach for the Highly Cis-Selective Synthesis of N-Benzoylaziridines and the Green Synthesis of 1,4,2-Dioxazoles as Two Important Classes of Heterocyclic Compounds. Org. Lett 2019, 21, 22-26. DOI: 10.1002/jhet.1972.
  • (a) Grünanger, P.; Vita-Finzi, P. Isoxazoles. In The Chemistry of Heterocyclic Compounds; John Wiley: New York, NY, 1991. (b) Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. Rings in Drugs. J. Med. Chem. 2014, 57, 5845-5859.
  • Kozikowski, A. P. The Isoxazoline Route to the Molecules of Nature. Acc. Chem. Res. 1984, 17, 410-416. DOI: 10.1021/ar00108a001.
  • (a) Pinho, e. M.; Teresa, M. V. D. Recent Advances on the Synthesis and Reactivity of Isoxazoles. Curr. Org. Chem. 2005, 9, 925-958. (b) Heaney, F. Nitrile Oxide/Alkyne Cycloadditions-a Credible Platform for Synthesis of Bioinspired Molecules by Metal-Free Molecular Clicking. Eur. J. Org. Chem. 2012, 2012, 3043-3058. DOI: 10.1002/ejoc.201101823. (c) Hu, F.; Szostak, M. Recent Developments in the Synthesis and Reactivity of Isoxazoles: Metal Catalysis and beyond. Adv. Synth. Catal. 2015, 357, 2583-2614. (d) Singh, M. S.; Chowdhury, S.; Koley, S. Progress in 1,3-Dipolar Cycloadditions in the Recent Decade: An Update to Strategic Development towards the Arsenal of Organic Synthesis. Tetrahedron 2016, 72, 1603-1644. (e) Morita, T.; Yugandar, S.; Fuse, S.; Nakamura, H. Recent Progresses in the Synthesis of Functionalized Isoxazoles. Tetrahedron Lett. 2018, 59, 1159-1171.
  • (a) Efimov, I.; Bakulev, V.; Beliaev, N.; Beryozkina, T.; Knippschild, U.; Leban, J.; Fan, Z.-J.; Eltsov, O.; Slepukhin, P.; Ezhikova, M.; Dehaen, W. Reactions of β-Azolylenamines with Sulfonyl Azides as an Approach to N-Unsubstituted 1,2,3-Triazoles and Ethene-1,2-Diamines. Eur. J. Org. Chem. 2014, 2014, 3684-3689. DOI: 10.1002/ejoc.201402130. (b) Kuribayashi, S.; Shida, N.; Inagi, S.; Fuchigami, T. Synthesis of Fluorinated Triazole and Isoxazole Derivatives by Electrochemical Fluorination. Tetrahedron 2016, 72, 5343-5349. (c) Wang, Q.; Lou, J.; Wu, P.; Wu, K.; Yu, Z. One-Pot Synthesis of 4-Heteroaryl-Substituted Pyrazoles: A Gold-Catalyzed Oxidation/1,2-Eeteroaryl Migration Cascade Constitutes the Key Step. Adv. Synth. Catal. 2017, 359, 2981-2998. (d) Andreev, M. V.; Medvedeva, A. S.; Larina, L. L.; Demina, M. M. Synthesis of 5-Aminoisoxazoles from 3-Trimethylsilylprop-2-Ynamides. Mendeleev Commun. 2017, 27, 175-177.
  • (a) Auricchio, S.; Ricca, A.; De Pava, O. V. Synthesis of Tris and Tetraisoxazole Compounds. J. Heterocyclic Chem. 1977, 14, 667-669. DOI: 10.1002/jhet.5570140425. (b) Neidlein, R.; Bischer, A.; Kramer, W. Reaktionsverhalten Tricyclischer 4H, 8H-Benzo[1,2-c: 4,5-c′]-Diisoxazol-4,8-Dione Gegenüber Reduktionsmitteln. Helv. Chim. Acta 1990, 73, 2147-2156. (c) Kantorowski, E. J.; Kurth, M. J. Solid-Phase Synthesis of Isoxazoles and Isoxazolines: En Route to a New Class of Ionophores. J. Org. Chem. 1997, 62, 6797-6803. (d) Sammelson, R. E.; Miller, R. B.; Kurth, M. J. Linear Tetraheterocycles Composed of Both Bidentate Diisoxazole and Bidentate Isoxazole-Furyl/Thienyl/Pyridyl Motifs. J. Org. Chem. 2000, 65, 2225-2228. (e) van der Peet, P. L.; Connell, T. U.; Gunawan, C.; White, J. M.; Donnelly, P. S.; Williams, S. J. A Click Chemistry Approach to 5,5′-Disubstituted-3,3′-Bisisoxazoles from Dichloroglyoxime and Alkynes: Luminescent Organometallic Iridium and Rhenium Bisisoxazole Complexes. J. Org. Chem. 2013, 78, 7298-7304. (f) Lee, Y.-G.; Koyama, Y.; Yonekawa, M.; Takata, T. New Click Chemistry: Polymerization Based on 1,3-Dipolar Cycloaddition of a Homo Ditopic Nitrile N-Oxide and Transformation of the Resulting Polymers into Reactive Polymers. Macromolecules 2009, 42, 7709-7717.
  • (a) Wu, G.-J.; Sheng, S.-R.; Li, D.; Xu, L.-F.; Huang, Z.-Z. Polymer-Supported Vinyl Sulfone as an Efficient Reagent for the Synthesis of 3-Monosubstituted Isoxazoles. Synth. Commun. 2013, 43, 3034-3043. DOI: 10.1080/00397911.2012.762718. (b) Sheng, S.-R.; Sheng, W.-S.; Hu, Q.-S.; Qu, H.-E.; Cai, M.-Z. Synthesis of Ethyl Isoxazole-3-Carboxylates Using an Ionic Liquid as a Soluble Support. J. Heterocyclic Chem. 2014, 51, 315-321.
  • Kim, Y. M.; Lee, S.; Kim, S. H.; Kim, J. N. An Efficient Indium-Mediated 2-Bromoallylation of Aldehydes at Low Temperature in Aqueous DMF. Tetrahedron Lett. 2011, 52, 3240-3242. DOI: 10.1016/j.tetlet.2011.04.053.
  • Bhat, L.; Steinig, A. G.; Appelbe, R.; de Meijere, A. Convenient Synthesis of Heterobicycles by Domino Heck-Diels-Alder Reactions. Eur. J. Org. Chem. 2001, 2001, 1673-1680. DOI: 10.1002/1099-0690(200105)2001:9<1673::AID-EJOC1673>3.0.CO;2-G.
  • Dadiboyena, S.; Xu, J. P.; Hamme, A. T. I. I. Isoxazoles from 1,1-Disubstituted Bromoalkenes. Tetrahedron Lett. 2007, 48, 1295-1298. DOI: 10.1016/j.tetlet.2006.12.005.
  • Dubrovskiy, A. V.; Larock, R. C. Synthesis of Benzisoxazoles by the [3 + 2] Cycloaddition of In Situ Generated Nitrile Oxides and Arynes. Org. Lett. 2010, 12, 1180-1183. DOI: 10.1021/ol902921s.

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