Unexpected Formation of Bis(hydrazinecarboximidamide) via Ultrasound Promoted Rearrangement of Epoxy Ketone

Autor: Silvania Rizzi Brasil, Adriana do Carmo Capiotto, Alex Fabiani Claro Flores, Davi Fernando Back, Eliandro Faoro, Lucas Pizzuti
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Zdroj: Orbital: The Electronic Journal of Chemistry, Vol 9, Iss 3, Pp 204-209 (2017)
Druh dokumentu: article
ISSN: 1984-6428
DOI: 10.17807/orbital.v9i3.972
Popis: An efficient synthesis of aromatic pyrazoles via cyclocondensation of epoxy chalcones with hydrazine is reported. When aminoguanidine hydrochloride is the dinucleophilic specie the reaction leads to a mixture of amidino pyrazole and a minor amount (15%) of an interesting co-product identified as 2,2'-(1,3-diphenylpropane-1,2-diylidene)bis(hydrazinecarboximidamide) dihydrochloride by X-ray diffraction and NMR. A plausible mechanism for the co-product formation via rearrangement of the epoxy chalcone into 1,2-diketone followed by the condensation with aminoguanidine reaction is proposed. DOI: http://dx.doi.org/10.17807/orbital.v9i3.972
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