The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study
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...
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| Format: | Article |
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2021-09-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/17/9646 |
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| author | Elena Chugunova Almir Gazizov Daut Islamov Alexander Burilov Alena Tulesinova Sergey Kharlamov Victor Syakaev Vasily Babaev Nurgali Akylbekov Nurbol Appazov Konstantin Usachev Rakhmetulla Zhapparbergenov |
| author_facet | Elena Chugunova Almir Gazizov Daut Islamov Alexander Burilov Alena Tulesinova Sergey Kharlamov Victor Syakaev Vasily Babaev Nurgali Akylbekov Nurbol Appazov Konstantin Usachev Rakhmetulla Zhapparbergenov |
| author_sort | Elena Chugunova |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T08:09:33Z |
| format | Article |
| id | doaj.art-2e1cd955e94b488299d0f8349996949f |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T08:09:33Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-2e1cd955e94b488299d0f8349996949f2023-11-22T10:46:45ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-09-012217964610.3390/ijms22179646The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism StudyElena Chugunova0Almir Gazizov1Daut Islamov2Alexander Burilov3Alena Tulesinova4Sergey Kharlamov5Victor Syakaev6Vasily Babaev7Nurgali Akylbekov8Nurbol Appazov9Konstantin Usachev10Rakhmetulla Zhapparbergenov11Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, RussiaInstitute of Chemical Engineering and Technology, The Kazan National Research Technological University, 420015 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, RussiaLaboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University, Aitekebie Str. 29A, Kyzylorda 120014, KazakhstanLaboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University, Aitekebie Str. 29A, Kyzylorda 120014, KazakhstanKazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center of Russian Academy of Sciences, 420111 Kazan, RussiaLaboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University, Aitekebie Str. 29A, Kyzylorda 120014, KazakhstanHerein, 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.https://www.mdpi.com/1422-0067/22/17/9646benzofuroxan1,3-dicarbonyl compoundsRegitz diazo transfertautomerism |
| spellingShingle | Elena Chugunova Almir Gazizov Daut Islamov Alexander Burilov Alena Tulesinova Sergey Kharlamov Victor Syakaev Vasily Babaev Nurgali Akylbekov Nurbol Appazov Konstantin Usachev Rakhmetulla Zhapparbergenov The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study International Journal of Molecular Sciences benzofuroxan 1,3-dicarbonyl compounds Regitz diazo transfer tautomerism |
| title | The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study |
| title_full | The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study |
| title_fullStr | The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study |
| title_full_unstemmed | The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study |
| title_short | The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study |
| title_sort | reactivity of azidonitrobenzofuroxans towards 1 3 dicarbonyl compounds unexpected formation of amino derivative via the regitz diazo transfer and tautomerism study |
| topic | benzofuroxan 1,3-dicarbonyl compounds Regitz diazo transfer tautomerism |
| url | https://www.mdpi.com/1422-0067/22/17/9646 |
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