期刊
TETRAHEDRON LETTERS
卷 46, 期 16, 页码 2915-2918出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.02.153
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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. (c) 2005 Elsevier Ltd. All rights reserved.
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