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Synthesis 2019; 51(08): 1809-1818
DOI: 10.1055/s-0037-1611703
DOI: 10.1055/s-0037-1611703
paper
A Tandem Sulfonylation and Knoevenagel Condensation for the Preparation of Sulfocoumarin-3-carboxylates
This work is financially supported by the National Natural Science Foundation of China (No. 21602010 to Z.Y., and No. 21572017 to J.X.), the BUCT Fund for Discipline Construction and Development (Project No. XK1533, to Z.Y.), the China Postdoctoral Science Foundation (No. 2016M600900, to Z.Y.), and the Fundamental Research Funds for the Central Universities (XK1802-6, to Z.Y. and J.X.).Weitere Informationen
Publikationsverlauf
Received: 20. September 2018
Accepted after revision: 27. November 2018
Publikationsdatum:
24. Januar 2019 (online)
‡ These authors contributed equally to this work.
Abstract
Sulfocoumarins are key structural motifs in several bioactive molecules. Herein, we describe a simple, one-pot procedure for the synthesis of structurally diverse sulfonocoumarin-3-carboxylates by heating 2-hydroxyaryl aldehydes with an active sulfonyl chloride in the presence of pyridine. The process tolerates numerous functional groups including alkoxy, alkyl, halogen, nitro, and even nucleophilic phenolic hydroxy. Additionally, reactions of 2-hydroxyaryl ketones and 2-methylaminoaryl aldehydes give 4-substituted sulfocoumarins and 1-aza-2-sulfocoumarins, respectively. A gram-scale synthesis and further derivatizations are also reported. The ester group is easily removed via Happer’s decarboxylation.
Key words
sulfocoumarin-3-carboxylates - tandem reactions - sulfonylation - Knoevenagel condensation - salicylaldehydeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611703.
- Supporting Information
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