One-Step Synthesis of Methoxylated Phloroglucinol Derivatives Promoted by Niobium Pentachloride: An Experimental and Theoretical Approach

Willian Henrique dos Santos; Eliezer Fernando de Oliveira; Francisco Carlos Lavarda; Ives Antonio Leonarczyk; Marco Antonio Barbosa Ferreira; Luiz Carlos da Silva-Filho

doi:10.1055/s-0036-1588730

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(11): 2402-2410
DOI: 10.1055/s-0036-1588730

paper

One-Step Synthesis of Methoxylated Phloroglucinol Derivatives Promoted by Niobium Pentachloride: An Experimental and Theoretical Approach

Willian Henrique dos Santos

^aDepartment of Chemistry, Faculty of Sciences, São Paulo State University (UNESP), 17033-360, Bauru, São Paulo, Brazil

,

Eliezer Fernando de Oliveira

^bDepartment of Physics, Faculty of Sciences, São Paulo State University (UNESP), 17033-360, Bauru, São Paulo, Brazil

,

Francisco Carlos Lavarda

^bDepartment of Physics, Faculty of Sciences, São Paulo State University (UNESP), 17033-360, Bauru, São Paulo, Brazil

,

Ives Antonio Leonarczyk

^cDepartment of Chemistry, Federal University of São Carlos (UFSCar), Rodovia Washington Luís, km 235 - SP-310, São Carlos, São Paulo, Brazil eMail: lcsilva@fc.unesp.br

,

Marco Antonio Barbosa Ferreira

^cDepartment of Chemistry, Federal University of São Carlos (UFSCar), Rodovia Washington Luís, km 235 - SP-310, São Carlos, São Paulo, Brazil eMail: lcsilva@fc.unesp.br

,

Luiz Carlos da Silva-Filho*

^aDepartment of Chemistry, Faculty of Sciences, São Paulo State University (UNESP), 17033-360, Bauru, São Paulo, Brazil

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Abstract

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Abstract

Phloroglucinol derivatives are an important class of natural compounds featuring the rhodomyrtone derivatives. In this work, the synthesis of compounds with a structure core of rhodomyrtosone I is described using a multicomponent reaction between aldehyde derivatives, dihydroresorcinol, and 3,5-dimethoxyphenol promoted by niobium pentachloride. This new method is simple, cost-effective, and provides a good yield. In addition, it can be conducted in good reaction times. Using Density Functional Theory (DFT) studies, bases are provided for a proposed reaction mechanism for the multicomponent reaction by exploring the energetics of proposed reactive intermediates and transition states.

Key words

niobium pentachloride - Lewis acid - phloroglucinol derivatives - multicomponent reactions - DFT studies

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