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Review

Alkoxyalkylation of Electron-Rich Aromatic Compounds

1
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary
2
HUN REN SZTE Stereochemistry Research Group, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2024, 25(13), 6966; https://doi.org/10.3390/ijms25136966
Submission received: 30 May 2024 / Revised: 17 June 2024 / Accepted: 20 June 2024 / Published: 26 June 2024

Abstract

Alkoxyalkylation and hydroxyalkylation methods utilizing oxo-compound derivatives such as aldehydes, acetals or acetylenes and various alcohols or water are widely used tools in preparative organic chemistry to synthesize bioactive compounds, biosensors, supramolecular compounds and petrochemicals. The syntheses of such molecules of broad relevance are facilitated by acid, base or heterogenous catalysis. However, degradation of the N-analogous Mannich bases are reported to yield alkoxyalkyl derivatives via the retro-Mannich reaction. The mutual derivative of all mentioned species are quinone methides, which are reported to form under both alkoxy- and aminoalkylative conditions and via the degradation of the Mannich-products. The aim of this review is to summarize the alkoxyalkylation (most commonly alkoxymethylation) of electron-rich arenes sorted by the methods of alkoxyalkylation (direct or via retro-Mannich reaction) and the substrate arenes, such as phenolic and derived carbocycles, heterocycles and the widely examined indole derivatives.
Keywords: alkoxyalkylation; alkoxymethylation; hydroxyalkylation; Mannich reaction; retro-Mannich reaction; indole; phenol; hydroxyquinoline; quinone methides alkoxyalkylation; alkoxymethylation; hydroxyalkylation; Mannich reaction; retro-Mannich reaction; indole; phenol; hydroxyquinoline; quinone methides

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MDPI and ACS Style

Simon, P.; Lőrinczi, B.; Szatmári, I. Alkoxyalkylation of Electron-Rich Aromatic Compounds. Int. J. Mol. Sci. 2024, 25, 6966. https://doi.org/10.3390/ijms25136966

AMA Style

Simon P, Lőrinczi B, Szatmári I. Alkoxyalkylation of Electron-Rich Aromatic Compounds. International Journal of Molecular Sciences. 2024; 25(13):6966. https://doi.org/10.3390/ijms25136966

Chicago/Turabian Style

Simon, Péter, Bálint Lőrinczi, and István Szatmári. 2024. "Alkoxyalkylation of Electron-Rich Aromatic Compounds" International Journal of Molecular Sciences 25, no. 13: 6966. https://doi.org/10.3390/ijms25136966

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