An Unusual Rearrangement of Pyrazole Nitrene and Coarctate Ring-Opening/Recyclization Cascade: Formal CH–Acetoxylation and Azide/Amine Conversion without External Oxidants and Reductants
Chugunova E. Gazizov A.S. Islamov D. Matveeva V. Burilov A. Akylbekov N. Dobrynin A. Zhapparbergenov R. Appazov N. Chabuka B.K. Christopher K. Tonkoglazova D.I. Alabugin I.V.
November 2023Multidisciplinary Digital Publishing Institute (MDPI)
Molecules
2023#28Issue 21
We report an unusual transformation where the transient formation of a nitrene moiety initiates a sequence of steps leading to remote oxidative C–H functionalization (R–CH3 to R–CH2OC(O)R’) and the concomitant reduction of the nitrene into an amino group. No external oxidants or reductants are needed for this formal molecular comproportionation. Detected and isolated intermediates and computational analysis suggest that the process occurs with pyrazole ring opening and recyclization.
1H-pyrazole , cyclization , fragmentation , furoxan , nitrene
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Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan, 420088, Russian Federation
Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University, Aitekebie Str. 29A, Kyzylorda, 120014, Kazakhstan
Zhakhaev Kazakh Scientific Research Institute of Rice Growing, Abay Av. 25B, Kyzylorda, 120008, Kazakhstan
Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, 32306-3290, FL, United States
Arbuzov Institute of Organic and Physical Chemistry
Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”
Zhakhaev Kazakh Scientific Research Institute of Rice Growing
Department of Chemistry and Biochemistry
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