Eco-friendly and regioselective synthesis of 3-(isoxazol-5)-yl) indoles from β -ethylthio- β -indolyl-α, β -unsaturated ketones in water

Eco-friendly and regioselective synthesis of 3-(isoxazol-5)-yl)indoles had been developed from the cyclocondensation reaction of β-ethyltho-β-indolyl-α, β-unsaturated ketones and hydroxyl -amine hydrochloride. It was found that in the presence of 1 equivalent of 4-dodecylbenzene sulfonic acid (DBSA)...

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Bibliographic Details
Published in:Synthetic communications 2021-05, Vol.51 (10), p.1581-1587
Main Authors: Jia, Jia, Su, Ye, Yu, Hai-Feng, Du, Hai-Tao, Mei, Ze-Min
Format: Article
Language:English
Subjects:
3-isoxazolindoles
Aqueous synthesis
hydroxylamine hydro-chloride
Indoles
Ketones
Regioselectivity
Substrates
Sulfonic acid
Synthesis
β-ethylthio-β-indolyl-α
β-unsaturatedketones
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Summary:Eco-friendly and regioselective synthesis of 3-(isoxazol-5)-yl)indoles had been developed from the cyclocondensation reaction of β-ethyltho-β-indolyl-α, β-unsaturated ketones and hydroxyl -amine hydrochloride. It was found that in the presence of 1 equivalent of 4-dodecylbenzene sulfonic acid (DBSA) in boiling water, β-ethyltho-β-indolyl-α, β-unsaturated ketones efficiently reacted with hydroxylamine hydrochloride to afford 3-(isoxazol-5)-yl)indoles in good yields and with good to excellent regioselectivity. The method features the advantages of eco-friendly process, good yield and regioselevtivity, operational simplicity, broad substrate scope and ease of scale-up.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2021.1894339