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Synthesis 2017; 49(11): 2402-2410
DOI: 10.1055/s-0036-1588730
paper
© Georg Thieme Verlag Stuttgart · New York

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

Willian Henrique dos Santos
a   Department of Chemistry, Faculty of Sciences, São Paulo State University (UNESP), 17033-360, Bauru, São Paulo, Brazil
,
Eliezer Fernando de Oliveira
b   Department of Physics, Faculty of Sciences, São Paulo State University (UNESP), 17033-360, Bauru, São Paulo, Brazil
,
Francisco Carlos Lavarda
b   Department of Physics, Faculty of Sciences, São Paulo State University (UNESP), 17033-360, Bauru, São Paulo, Brazil
,
Ives Antonio Leonarczyk
c   Department 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
c   Department 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*
a   Department of Chemistry, Faculty of Sciences, São Paulo State University (UNESP), 17033-360, Bauru, São Paulo, Brazil
› Author Affiliations
Further Information

Publication History

Received: 30 November 2016

Accepted after revision: 30 January 2017

Publication Date:
22 February 2017 (online)

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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

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588730.
  • Supporting Information
 

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