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

Author(s)

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

• Document type: Journal article
• Source: SYNTHESIS-STUTTGART; v. 49, n. 11, p. 2402-2410, JUN 2017.
• Web of Science Citations: 6

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. (AU)

• FAPESP's process: 15/08541-6 - Nuclear magnetic resonance spectroscopy: beyond molecular structure assignment
• Grantee: Claudio Francisco Tormena
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 16/01599-1 - Studies about the use of NbCl5 in multicomponent reactions for the synthesis of organic dyes
• Grantee: Luiz Carlos da Silva Filho
• Support Opportunities: Regular Research Grants
• FAPESP's process: 12/21983-0 - ELECTRONIC STRUCTURE OF ORGANIC MATERIALS FOR APPLICATIONS IN SOLAR CELLS' ACTIVE LAYERS
• Grantee: Eliezer Fernando de Oliveira
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 14/20410-1 - Electronic structure of organic materials for applications in the active layer of solar cells
• Grantee: Francisco Carlos Lavarda
• Support Opportunities: Regular Research Grants