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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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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles