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DOI: 10.1055/a-2189-3334
Truly Catalytic Gewald Synthesis of 2-Aminothiophenes Using Piperidinium Borate (Pip Borate), a Conjugate Acid–Base Pair
This work was supported by the Council of Scientific and Industrial Research New Delhi, India, under grant (09/991(00062)/2020-EMR-I).
Abstract
The Gewald reaction has been well-known for more than half a century as an excellent method to provide bioactive 2-aminothiophene heterocycles from the reaction of carbonyl compounds, α-cyanoacetates, and elemental sulfur, in the presence of amines, in stoichiometric amounts. This work describes the use of salts of boric acid as conjugate acid-base pairs in a truly catalytic amount for the cyclocondensation of ketones with active methylenes such as malononitrile, ethyl cyanoacetate, and benzoyl acetonitrile with sulfur to give 2-aminothiophenes via the Gewald reaction. The present protocol is also applied for synthesizing Tinoridine, an anti-peroxidative NSAID, with excellent yield. Additionally, the catalyst has great recyclability and reusability.
Key words
conjugate acid-base catalyst - Gewald reaction - 2-aminothiophenes - recyclable - piperidinium borateSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2189-3334.
- Supporting Information
Publication History
Received: 05 September 2023
Accepted after revision: 09 October 2023
Accepted Manuscript online:
10 October 2023
Article published online:
23 November 2023
© 2023. The Author(s). 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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