66838-69-5Relevant articles and documents
uses of β-diketones for the synthesis of novel heterocyclic compounds and their antitumor evaluations
Kamel, Mona M.,Milad, Yara R.,Mohareb, Rafat M.
, p. 385 - 405 (2020)
The reaction of the 3-oxo-N,3-diphenylpropan-amide (3) with either malononitrile or ethyl cyanoacetate in ammonium acetate gave the 1,2-dihydropyridine derivatives 6a or 6b, respectively. On the other hand, carrying the same reaction in the presence of triethylamine gave the 1,6-dihydropyridine derivatives 7a and 7b, respectively. Moreover, compound 3 reacted with 2-aminoprop-1-ene-1,1,3-tricarbonitrile to give the pyridine derivative 9. Compound 7b reacted with the active methylene derivatives 10a,b and 4a,b to give the naphthyridine derivatives 11a,b and 12a,b; respectively. Compound 3 was also used for the synthesis of thiophene derivatives 13a,b and 16a,b. In addition, the reaction of ethyl benzoylacetate (1) with o-phenylene diamine gave the benzimidazole derivative 18. The reactivity of the latter product towards different reagents was studied to give different products. The cytotoxicity of the newly synthesized products was studied towards some cancer and normal cell lines, in addition toxicity of compounds was measured and docking of the most active compounds was done. Compounds 6b, 7b, 9, 13a, 13b, 16a, 20b, 20c, 24b, 25 and 26b exhibited optimal cytotoxic effect against cancer tested cell lines. These active compounds were evaluated against c-Met kinase using foretinib as the reference drug where all compounds expressed higher activity than the reference drug.
Tautomeric equilibria in solutions of 2-phenacylbenzimidazoles
Skotnicka, Agnieszka,Czeleń, Przemys?aw,Gawinecki, Ryszard
, (2019/04/25)
Detailed NMR spectral analysis of DMSO-d6 solutions of the series of substituted 2-phenacylbenzimidazoles (ketimine form, K) reveals two from three tautomeric forms. Integrals of the 1H NMR signals are used in establishing the molar ratio of tautomers. The experimental analyses are supported by quantum-chemical calculations, which satisfactorily reproduced the experimental trends. Although the reported semiempirical quantum-chemical calculations show that enaminone E, i.e., 2-(1,3-dihydro-2H-benzo[d]imidazol-2-ylidene)-1-phenylethan-1-one, was thermodynamically most stable, the results of MP2 ab initio calculations reveal the following order of stability: Ketimine > enolimine > enaminone (substituents do not affect this sequence). 13C CPMAS NMR spectral data reveal that in the crystalline state the enolimine tautomer O is predominant in the p-CH3 and p-NO2 substituted congeners.
ABNORMAL DIRECTION IN THE REACTION OF ALKYL β,β-DICHLOROVINYL KETONES WITH o-PHENYLENDIAMINE
Levkovskaya, G.G.,Mirskova, A.N.,Kalikhman, I.D.,Voronkov, M.G.
, p. 575 - 579 (2007/10/02)
The reaction of methyl and propyl β,β-dichlorovinyl ketones with o-phenylendiamine leads to 2-methylbenzimidazole and to a mixture of 2-methyl and 2-propylbenzimidazoles respectively.Chloromethyl and phenyl β,β-dichlorovinylketones react with o-phenylenediamine to form 2-(3-chloro-2-oxopropyl) and 2-(2-phenyl-2-oxoethyl)benzimidazole respectively.The synthesized benzimidazoles form hydrochlorides and are nitrated in the aromatic ring.2-(3-Chloro-2-oxopropyl)benzimidazole 2,4-dinitrophenylhydrazone was obtained.
