Synthesis of tetrahydropiridines by one-pot multicomponent reaction using Niobium Pentaethoxide

Autor: B. H. S. T. da Silva, Luiz Carlos da Silva-Filho, Lucas Michelão Martins
Rok vydání: 2013
Předmět:
Zdroj: Proceedings of the 15th Brazilian Meeting on Organic Synthesis Proceedings.
DOI: 10.5151/chempro-15bmos-bmos2013_2013926121740
Popis: In this work, we performed the Multicomponent Reaction between aniline derivatives(1-3), Benzaldehyde (4) and a β-ketoester, both methyl (5) and ethyl (6) acetoacetate. The aniline derivatives were aniline (1), pbromoaniline (2) and p-anisidine (3) in the presence of NbCl5. The reactions were carried out under nitrogen atmosphere, at room temperature and in anhydrous solvent (CH3CN), using 1 mmol of NbCl5. The stoichiometric ratio 2:2:1 (aldehyde:aniline:βketoester) in the presence of catalyst was found to be the most suitable condition for obtaining functionalized tetrahydropiridines. The reaction proceeded smoothly at room temperature, the reactions were monitored for a maximum time of 24 hours, since, for longer times was not observed significant changes in products yields, for all tetrahydropiridine derivatives synthetized. The product obtained was purified by column chromatography. The products were isolated and characterized by spectroscopic and spectrometric methods. The results are summarized in scheme 1 and table 1.
Databáze: OpenAIRE