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Synthesis 2021; 53(11): 1989-1999
DOI: 10.1055/s-0040-1706658
DOI: 10.1055/s-0040-1706658
paper
Complementary and Regioselective Synthesis of Isomeric 3-[Isoxazol-3(or 5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones
This work was supported by the Foundation of Education Department of Jilin Province [JJKH20200001KJ, JJKH2016037KJ].
Abstract
A simple and efficient method for the complementary and regioselective synthesis of isomeric 3-(isoxazol-5-yl)indoles and 3-(isoxazol-3-yl)indoles has been developed by the regioselective cyclocondensation reaction of β-ethylthio-β-indolyl-α,β-unsaturated ketones and hydroxylamine hydrochloride. It was found that the cyclocondensation reaction in the presence of excess NaOEt in refluxing EtOH gives 3-(isoxazol-5-yl)indoles in good yields, whereas using NaOAc in boiling AcOH gives 3-(isoxazol-3-yl)indoles in good yields.
Key words
unsaturated ketones - isoxazole - indole - hydroxylamine hydrochloride - regioselectivity - cyclocondensation reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706658.
- Supporting Information
Publication History
Received: 01 September 2020
Accepted after revision: 02 December 2020
Article published online:
11 January 2021
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