Cargando…

On the Question of the Formation of Nitro-Functionalized 2,4-Pyrazole Analogs on the Basis of Nitrylimine Molecular Systems and 3,3,3-Trichloro-1-Nitroprop-1-Ene

Experimental and theoretical studies on the reaction between (E)-3,3,3-trichloro-1-nitroprop-1-ene and N-(4-bromophenyl)-C-arylnitrylimine were performed. It was found that the title process unexpectedly led to 1-(4-bromophenyl)-3-phenyl-5-nitropyrazole instead of the expected Δ(2)-pyrazoline molecu...

Descripción completa

Detalles Bibliográficos
Autores principales: Kula, Karolina, Łapczuk, Agnieszka, Sadowski, Mikołaj, Kras, Jowita, Zawadzińska, Karolina, Demchuk, Oleg M., Gaurav, Gajendra Kumar, Wróblewska, Aneta, Jasiński, Radomir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9739753/
https://www.ncbi.nlm.nih.gov/pubmed/36500503
http://dx.doi.org/10.3390/molecules27238409
Descripción
Sumario:Experimental and theoretical studies on the reaction between (E)-3,3,3-trichloro-1-nitroprop-1-ene and N-(4-bromophenyl)-C-arylnitrylimine were performed. It was found that the title process unexpectedly led to 1-(4-bromophenyl)-3-phenyl-5-nitropyrazole instead of the expected Δ(2)-pyrazoline molecular system. This was the result of a unique CHCl(3) elimination process. The observed mechanism of transformation was explained in the framework of the molecular electron density theory (MEDT). The theoretical results showed that both of the possible channels of [3 + 2] cycloaddition were favorable from a kinetic point of view, due to which the creation of 1-(4-bromophenyl)-3-aryl-4-tricholomethyl-5-nitro-Δ(2)-pyrazoline was more probable. On the other hand, according to the experimental data, the presented reactions occurred with full regioselectivity.