The reactivity of azidonitrobenzofuroxans towards 1,3-dicarbonyl compounds: Unexpected formation of amino derivative via the regitz diazo transfer and tautomerism study
Chugunova E. Gazizov A. Islamov D. Burilov A. Tulesinova A. Kharlamov S. Syakaev V. Babaev V. Akylbekov N. Appazov N. Usachev K. Zhapparbergenov R.
September 2021MDPI
International Journal of Molecular Sciences
2021#22Issue 17
Herein, we report on the reaction of nitro-substituted azidobenzofuroxans with 1,3-dicarbonyl compounds in basic media. The known reactions of benzofuroxans and azidofuroxans with 1,3-dicarbonyl compounds in the presence of bases are the 1,3-dipolar cycloaddition and the Beirut reaction. In contrast with this, azidonitrobenzofuroxan reacts with 1,3-carbonyl compounds through Regitz diazo transfer, which is the first example of this type of reaction for furoxan derivatives. This difference is seemingly due to the strong electron-withdrawing effect of the superelectrophilic azidonitrobenzofuroxan, which serves as the azido transfer agent rather than 1,3-dipole in this case.
1,3-dicarbonyl compounds , Benzofuroxan , Regitz diazo transfer , Tautomerism
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Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Kazan, 420088, Russian Federation
Laboratory of Plant Infectious Diseases, FRC Kazan Scientific Center of Russian Academy of Sciences, Kazan, 420111, Russian Federation
Institute of Chemical Engineering and Technology, The Kazan National Research Technological University, Kazan, 420015, Russian Federation
Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University, Aitekebie Str. 29A, Kyzylorda, 120014, Kazakhstan
I. Zhakhaev Kazakh Scientific Research Institute of Rice Growing, AbayAvenue 25B, Kyzylorda, 120008, Kazakhstan
Kazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center of Russian Academy of Sciences, Kazan, 420111, Russian Federation
Arbuzov Institute of Organic and Physical Chemistry
Laboratory of Plant Infectious Diseases
Institute of Chemical Engineering and Technology
Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”
I. Zhakhaev Kazakh Scientific Research Institute of Rice Growing
Kazan Institute of Biochemistry and Biophysics
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