Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 11, Pages 1989-1999Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1706658
Keywords
unsaturated ketones; isoxazole; indole; hydroxylamine hydrochloride; regioselectivity; cyclocondensation reaction
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Funding
- Foundation of Education Department of Jilin Province [JJKH20200001KJ, JJKH2016037KJ]
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The efficient method developed allows for complementary and regioselective synthesis of isomeric 3-(isoxazol-5-yl)indoles and 3-(isoxazol-3-yl)indoles through the regioselective cyclocondensation reaction, with good yields achieved using different conditions.
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 beta-ethylthio-beta-indolyl-alpha,beta-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.
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