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DOI: 10.1055/s-0040-1719922
Synthesis of 2,3-Diarylquinoxaline Carboxylic Acids in High-Temperature Water
This work was funded by the Vienna Science and Technology Fund (WWTF) (Grant No. LS17-051) and the Austrian Science Fund (FWF) (Grant No. START Y1037-N28).
Abstract
Aromatic carboxylic acids are prone to decarboxylate in high-temperature water (HTW). While the decarboxylation kinetics of several aromatic carboxylic acids have been explored, studies on their compatibility with organic syntheses in HTW are scarce. Herein, we report the hydrothermal synthesis (HTS) of 2,3-diarylquinoxaline carboxylic acids from 1,2-diarylketones and 3,4-diaminobenzoic acid. A detailed study of the reaction parameters was performed to identify reaction conditions towards minimal decarboxylation. Thirteen 2,3-diarylquinoxaline-6-carboxylic acids are obtained at temperatures between 150–230 °C within 5–30 minutes. The reported conditions feature comparable performance to those of classic syntheses, avoiding volatile organic solvents, strong acids and toxic catalysts. Decarboxylated quinoxalines arise as side products in variable amounts via direct decarboxylation of the 3,4-diaminobenzoic acid. To completely inhibit the decarboxylation, we show that suitable structural analogues of 3,4-diaminobenzoic acid can act as starting compounds. Thus, ester hydrolysis of methyl 3,4-diaminobenzoate and deprotection of di-Boc-protected 3,4-diminobenzoic can be coupled with the HTS of quinoxaline towards quinoxaline carboxylic acids, while fully avoiding decarboxylated side products.
Key words
quinoxalines - high-temperature water - green chemistry - decarboxylation - hydrothermal synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719922.
- Supporting Information
Publication History
Received: 09 March 2022
Accepted after revision: 07 April 2022
Article published online:
07 June 2022
© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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