Riseley, Ross, Carneiro, Aitor, Mu, Zhilin, Alkahtani, Rawiyah, Kariuki, Benson ORCID: https://orcid.org/0000-0002-8658-3897, Waller-Evans, Helen ORCID: https://orcid.org/0000-0003-4133-6064 and Jones, D. Heulyn
2025.
Unusual reactivity of 2-amino-1H-indole-3-carboxylate esters.
ARKIVOC
2025
(5)
, 202512417.
10.24820/ark.5550190.p012.417
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Official URL: http://dx.doi.org/10.24820/ark.5550190.p012.417
Abstract
We report the outcome of the attempted synthesis of amino-1H-indole-3-carboxylic acid from the corresponding ethyl and tert-butyl esters. Subjection of the tert-butyl ester to acidic conditions led to quantitative conversion to indolin-2-imine hydrochloride and the ethyl ester to basic conditions led to a ring-opened product, showing that the carboxylic acid is not easily-accessible via the corresponding esters. During the synthesis of the esters, the novel compound 2-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)phenol was isolated and was shown to be chiral due to atropisomerism.
| Item Type: | Article |
|---|---|
| Date Type: | Publication |
| Schools: | Schools > Chemistry Schools > Biosciences |
| Publisher: | ARKAT USA |
| ISSN: | 1551-7012 |
| Funders: | Coleg Cymraeg Cenedlaethol, Harrington Institute |
| Date of First Compliant Deposit: | 1 October 2025 |
| Date of Acceptance: | 25 July 2025 |
| Last Modified: | 01 Oct 2025 09:45 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/181418 |
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