Regioselective N- and C2-electrophilic substitution of 3-substituted indoles (short communication) | NOVA. The University of Newcastle's Digital Repository

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Please use this identifier to cite or link to this item: http://hdl.handle.net/1959.13/25394

Title: Regioselective N- and C2-electrophilic substitution of 3-substituted indoles (short communication)
Author/Creator: Leitch, Sarah; Addison-Jones, Jennifer; McCluskey, Adam
Description: The reaction of 3-substituted indoles with 2-cyclohexenone under Lewis acid mediated conditions with Bi(NO3)(3)-5H(2)O has been investigated. We have demonstrated that electrophilic substitution of 3-substituted indoles with 2-cyclohexenone will readily occur at the nitrogen. Furthermore, the extent of regioselectivity is dependent on reaction solvent and the C3-substituent. Excellent conversion is obtained with good to excellent isolated yields of N- and C2-adducts. In general, more polar, aprotic solvents (CH3CN) give greater N-selectivity whereas with polar protic solvents (CH3OH) an increase in the C2-adduct is observed.
Relation: Tetrahedron Letters Vol. 46, no. 16, p. 2915-2918
Date: 2005
Publisher: Pergamon Press
Keyword(s): efficient method; bismuth trichloride; aromatic-amines; mild; chemistry; harmicine; nitrate; system; alpha
Resource Type: journal article
Identifier: http://hdl.handle.net/1959.13/25394
Identifier: ISSN:0040-4039
Language: eng

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