Amidoxime-Functionalized (9,10-Dioxoantracen-1-yl)hydrazones
Affiliation:
Lviv Polytechnic National University,
12, Bandera St., 79013 Lviv, Ukraine
2 Institute of Organic Chemistry
of National Academy of Sciences of Ukraine,
5, Murmanska St., 02660 Kyiv, Ukraine
maryna.v.stasevych@gmail.com
DOI:
https://doi.org/10.23939/chcht13.04.417
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Keywords:
Abstract:
New (9,10-dioxoanthracen-1-yl)hydrazones containing amidoxime fragments were synthesized by the interaction of corresponding hydrazones of malonodinitrile, ethyl cyanacetate, ethyl acetoacetate, and acetylacetone with hydroxylamine in boiling dioxane in the presence of sodium acetate. It was established that the reaction of N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)carbonohydrazonoyldicyanide 1 with NH2OH leads to the formation of 2-(2-(9,10-dioxo-9,10-dihydroanthracen-1-yl)hydrazinylidene)-N'1,N'3-dihydroxymalonimidamide 2 as the major product, and 3-amino-2-(2-(9,10-dioxo-9,10-dihydroanthracen-1-yl)hydrazinylidene)-3-(hydroxyimino)propanamide 3 as a minor product. The 1H, 13C NMR and LC-MS data showed that the interaction of 9,10-dioxoanthracenylhydrazone of acetylacetone 5 by hydroxylamine is accompanied with the elimination of the acetyl fragment formed 1-[2-(2-(hydroxyimino)propylidene)hydrazinyl]anthracene-9,10-dione 9. Possible mechanisms for the formation of amidoximes 3 and 9 are proposed. Quantum-chemical DFT calculations of the Gibbs free energy (G) to determine conformational advantage of Z- or E-isomers for the amidoxime form of the derivatives 2,3,7-9 were carried out using the M06-2X hybrid method with 6-311++G(d, p) basis set and the SMD solvation model in DMSO.
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