Abstract:
A convenient procedure was developed for the synthesis of 5-aminoisoxazoles by the consecutive double silylation and cyanation of aliphatic nitro compounds.
Document Type:
Article
Language: English
Citation:
A. V. Lesiv, S. L. Ioffe, Yu. A. Strelenko, I. V. Bliznets, V. A. Tartakovsky, “Reactions of N,N-bis(siloxy)enamines with trimethylsilyl cyanide: aliphatic nitro compounds as convenient precursors of 5-aminoisoxazoles”, Mendeleev Commun., 12:3 (2002), 99–102
Linking options:
https://www.mathnet.ru/eng/mendc4112
https://www.mathnet.ru/eng/mendc/v12/i3/p99
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Pavel Yu. Ushakov, Andrey A. Tabolin, Sema L. Ioffe, Alexey Yu. Sukhorukov, “In Situ Generated Magnesium Cyanide as an Efficient Reagent for Nucleophilic Cyanation of Nitrosoalkenes and Parent Nitronates”, Eur J Org Chem, 2019:9 (2019), 1888
Bohdan A. Chalyk, Kateryna V. Hrebeniuk, Konstantin S. Gavrilenko, Oleh V. Shablykin, Oksana O. Yanshyna, Daniil Bash, Pavel K. Mykhailiuk, Oleksandr S. Liashuk, Oleksandr O. Grygorenko, “Synthesis of Bi‐ and Polyfunctional Isoxazoles from Amino Acid Derived Halogenoximes and Active Methylene Nitriles”, Eur J Org Chem, 2018:22 (2018), 2753
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M. V. Andreev, A. S. Medvedeva, L. I. Larina, M. M. Demina, “Synthesis of 5-aminoisoxazoles from 3-trimethylsilylprop-2-ynamides”, Mendeleev Commun., 27:2 (2017), 175–177
Andrey A. Tabolin, Sema L. Ioffe, “Rearrangement of N-Oxyenamines and Related Reactions”, Chem. Rev., 114:10 (2014), 5426
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V. I. Potkin, S. K. Petkevich, E. G. Zalesskaya, “Synthesis of functionally substituted isoxazoles from 5-(2,5-dimethylphenyl)-1,2-oxazole-3-carbonitrile”, Russ J Org Chem, 45:6 (2009), 879
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V. P. Kislyi, E. B. Danilova, V. V. Semenov, “Synthesis of 3,5-disubstituted 4-aminoisoxazoles by cyclization of O-(β-oxoalkyl)-substituted α-hydroxyimino nitriles”, Russ Chem Bull, 54:5 (2005), 1189
A. V. Lesiv, S. L. Ioffe, Yu. A. Strelenko, V. M. Danilenko, “Chemistry of N,N-bis(silyloxy)enamines 7. Quaternization of tertiary amines and nitrogen-containing heterocycles by N,N-bis(silyloxy)enamines”, Russ Chem Bull, 53:10 (2004), 2233
Aleksei V. Lesiv, Sema L. Ioffe, Yurii A. Strelenko, Igor' V. Bliznets, Vladimir A. Tartakovsky, “Reactions of N,N‐Bis(siloxy)enamines with Trimethylsilyl Cyanide: Aliphatic Nitro Compounds as Convenient Precursors of 5‐Aminoisoxazoles.”, ChemInform, 33:46 (2002), 146
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