Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles

Averina, Elena B.; Vasilenko, Dmitry A.; Samoilichenko, Yuri; Grishin, Yuri K.; Rybakov, Victor B.; Kuznetsova, Т. S.; Зефиров, Н. С.

doi:10.1055/s-0033-1340827

Cited by 17 publications

(6 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to molecular modeling, bis(5-aminoisoxazoles) can be of interest as bivalent modulators of the AMPA receptor and compound 6 is among the most promising ones based on the pharmacophore and QSAR models, the results of the molecular docking and molecular dynamics simulations, and the predicted physico-chemical and ADMET profiles. In view of this, we have studied the reduction of 5-nitro substituted heterocycle 3d in various conditions [12,13,42,43]. The attempt to reduce 5-nitroisoxazole 3d using SnCl 2 in EtOH failed due to its poor solubility, yet the application of the system Na 2 S 2 O 4 /THF/H 2 O allowed us to obtain the target bis(5-aminoisoxazole) 6 in a satisfactory yield (Scheme 3).…”

Section: Scheme 1 Heterocyclization Of the Adamantane-containing Diene 2gmentioning

confidence: 99%

A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor

et al. 2021

View full text Add to dashboard Cite

A convenient synthetic approach to novel functionalized bis(isoxazoles), the promising bivalent ligands of the AMPA receptor, was elaborated. It was based on the heterocyclization reactions of readily available electrophilic alkenes with the tetranitromethane-triethylamine complex. The structural diversity of the synthesized compounds was demonstrated. In the electrophysiological experiments using the patch clamp technique on Purkinje neurons, the compound 1,4-phenylenedi(methylene)bis(5-aminoisoxazole-3-carboxylate) was shown to be highly potent positive modulator of the AMPA receptor, potentiating kainate-induced currents up to 70% at 10−11 M.

show abstract

Section: Scheme 1 Heterocyclization Of the Adamantane-containing Diene 2gmentioning

confidence: 99%

A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The Averina group [15] elaborated the synthesis of 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles 15.1 from reactions between 5-nitroisoxazoles and THF. The process involved the reduction of 5-nitroisoxazoles 14.2 by SnCl2 and subsequent radical addition by radical 14.3.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

α-Csp3–H Bond Functionalization of Simple Ethers in Radical Reactions

Feng

Huang

et al. 2021

Synthesis

View full text Add to dashboard Cite

The direct α-Csp3-H functionalization of simple ethers has emerged as one of the vital strategies among radical reactions. This review discusses their applications according to the starting materials: (1) reactions with alkenes or alkynes. (2) reactions with other unsaturated compounds. (3) reactions with nucleophilic partners. Mechanisms like radical addition, elimination, oxidation, metal-catalyzed coupling, C-H activation, cyclization and rearrangement will be discussed herein.

show abstract

“…116 The elaborated method was used for the synthesis of a series of isoxazole derivatives with promising bioactivity. [119][120][121] The heterocyclization of electrophilic alkenes is proposed to proceed according to Scheme 31, starting from the polarization of the tetranitromethane molecule by treatment with triethylamine. The key stage of heterocyclization is Michael addition of the trinitromethyl anion to the C=C bond of the electrophilic alkene, while subsequent intramolecular cyclization of tetranitro-substituted intermediate I, accompanied by elimination of HNO 2 and HNO 3 , gives the target 5-nitroisoxazole II.…”

Section: Synthesis Using Polynitro Compoundsmentioning

confidence: 99%

Synthetic Approaches to Nitro-Substituted Isoxazoles

et al. 2019

Self Cite

View full text Add to dashboard Cite

Nitro-substituted isoxazoles are of utmost interest both as versatile intermediates for targeted organic synthesis and as perspective bioactive compounds for drug development. Nevertheless, the existing approaches to them usually lack generality and strongly depend on the position of the nitro group and on the presence of other substituents in the isoxazole ring. This review provides the first systematization of all available data concerning synthetic approaches to 3-, 4-, and 5-nitroisoxazoles. There are a number of preparative approaches to 4-nitroisoxazoles based on classical heterocyclization reactions of nitro-substituted compounds and the nitration of isoxazoles. 3-Nitro- and, especially, 5-nitroisoxazoles are much less readily available. A few methods affording 3-nitroisoxazoles have been reported, often employing the heterocyclization of unsaturated compounds by treatment with sodium nitrite. The sole general preparative method for 5-nitroisoxazoles, containing a variety of functional groups, employs the heterocyclization of electrophilic alkenes by treatment with tetranitromethane activated with triethylamine.1 Introduction2 Synthesis of 4-Nitroisoxazoles2.1 Nitration of Isoxazoles2.2 Condensations of α-Nitro Ketones or Their Oximes2.3 1,3-Dipolar Cycloaddition of Nitrile Oxides to Acetylenes and Their Synthetic Equivalents2.4 Heterocyclization of Acetylene Derivatives by Treatment with Sodium Nitrite2.5 Heterocyclization of Nitro Derivatives of 1,3-Diketones and Their Synthetic Equivalents2.6 Miscellaneous Methods3 Synthesis of 3-Nitroisoxazoles3.1 Heterocyclization of Acetylene Derivatives or 1,3-Dihalogenoalkenes by Treatment with Sodium Nitrite3.2 Heterocyclization of Morita–Baylis–Hillman Acetates by Treatment with Sodium Nitrite3.3 1,3-Dipolar Cycloadditions4 Synthesis of 5-Nitroisoxazoles4.1 1,3-Dipolar Cycloadditions4.2 Synthesis Using Polynitro Compounds5 Conclusion

show abstract

Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles

Cited by 17 publications

References 9 publications

A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor

A Facile Approach to Bis(isoxazoles), Promising Ligands of the AMPA Receptor

α-Csp3–H Bond Functionalization of Simple Ethers in Radical Reactions

Synthetic Approaches to Nitro-Substituted Isoxazoles

Contact Info

Product

Resources

About