130160-98-4Relevant academic research and scientific papers
Rapid, efficient, room temperature aromatization of Hantzsch-1,4-dihydropyridines with vanadium(V) salts: superiority of classical technique versus microwave promoted reaction
Filipan-Litvi?, Mirela,Litvi?, Mladen,Vinkovi?, Vladimir
, p. 10912 - 10918 (2008/12/23)
The aromatization of 1,4-dihydropyridines (1,4-DHPs) employing group 4 (Zr and Hf) and 5 (V, Nb, Ta) elements of periodic system has been studied. The reaction with VOCl3 in dichloromethane at room temperature afforded products, substituted pyridines, in high-to-excellent yield. For the first time, the formation of charge-transfer complexes (CTCs) has been evidenced in preorganization step between 1,4-DHP and oxidant before electron transfer. The CTC has been formed only in neutral solvents such as dichloromethane and is characterized by intensive coloration. The aromatization of 1,4-DHP with V2O5 in refluxing acetic acid has found to be superior over microwave promoted reaction in solventless media. The only reasonable explanation was found in polymeric structure of V2O5, which slowly transfer energy of microwaves needed for the activation of the reactants. The solvent polarity dependent oxidative dealkylation of 4-n-propyl-1,4-DHP has been discovered. Unexpectedly, the reaction in acetic acid afforded only 33% of dealkylated product compared to 91% obtained in dichloromethane under the same reaction conditions.
A highly efficient biomimetic aromatization of Hantzsch-1,4-dihydropyridines with t-butylhydroperoxide, catalysed by iron(III) phthalocyanine chloride
Filipan-Litvic, Mirela,Litvic, Mladen,Vinkovic, Vladimir
experimental part, p. 9276 - 9282 (2009/04/05)
Rapid aromatization of Hantzsch-1,4-DHPs with t-butylhydroperoxide catalysed by iron(III) phthalocyanine chloride is described. The reaction proceeds smoothly at room temperature within 1-35 min and the products of high purity were isolated in excellent yields. To explain the reactivity of this catalytical system plausible mechanism have been proposed to involve formation of high-valent oxoferryl species as in cytochrome P450 itself.
An efficient, metal-free, room temperature aromatization of Hantzsch-1,4-dihydropyridines with urea-hydrogen peroxide adduct, catalyzed by molecular iodine
Filipan-Litvi?, Mirela,Litvi?, Mladen,Vinkovi?, Vladimir
, p. 5649 - 5656 (2008/09/21)
A mild, highly efficient and metal-free synthetic method for aromatization of 1,4-dihydropyridines employing urea-hydrogen peroxide adduct as oxidant catalyzed by 20 mol % of molecular iodine was developed. The reaction was carried out in ethyl acetate at room temperature and the products were isolated in high to excellent yields. A plausible free-radical mechanism is proposed based on results obtained with derivatives having alkyl and aryl substituents in the 1,4-dihydropyridine ring.
