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Synthesis 2017; 49(11): 2402-2410
DOI: 10.1055/s-0036-1588730
DOI: 10.1055/s-0036-1588730
paper
One-Step Synthesis of Methoxylated Phloroglucinol Derivatives Promoted by Niobium Pentachloride: An Experimental and Theoretical Approach
Further Information
Publication History
Received: 30 November 2016
Accepted after revision: 30 January 2017
Publication Date:
22 February 2017 (online)
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 studiesSupporting 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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