- Title
- Regioselective N- and C2-electrophilic substitution of 3-substituted indoles (short communication)
- Creator
- Leitch, Sarah; Addison-Jones, Jennifer; McCluskey, Adam
- Relation
- Tetrahedron Letters Vol. 46, no. 16, p. 2915-2918
- Publisher
- Pergamon Press
- Resource Type
- journal article
- Date
- 2005
- 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.
- Subject
- efficient method; bismuth trichloride; aromatic-amines; mild; chemistry; harmicine; nitrate; system; alpha
- Identifier
- uon:366
- Identifier
- http://hdl.handle.net/1959.13/25394
- Identifier
- ISSN:0040-4039
- Language
- eng
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