Regioselective alkylation reactions of 2,4-diphenyl-3H-1-benzazepine give either 3-alkyl-3H-1-benzazepines or 1-alkyl-1H-1-benzazepines |
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| Authors: | Allen Ko Aaron Lam Jeffrey Li Edyta M Greer David J Szalda Sasan Karimi Gopal Subramaniam Keith Ramig |
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| Institution: | 1. Department of Natural Sciences, Baruch College of the City University of New York, 17 Lexington Ave., New York, NY 10010, USA;2. Department of Chemistry, Queensborough Community College of the City University of New York, 222-05 56th Ave., Bayside, NY 11364, USA;3. Department of Chemistry and Biochemistry, Queens College of the City University of New York, 65-30 Kissena Blvd., Flushing, NY 11367, USA |
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| Abstract: | 2,4-Diphenyl-3H-1-benzazepine is deprotonated with either LDA or KHMDS. The resulting anion is alkylated with alkyl halides or MeOTs, giving either products of alkylation at C3, or at N, or a mixture of both. The regioselectivity depends on the base, presence of the complexing agent HMPA, and the leaving group of the alkylating agent. Using MeI as alkylating agent gives exclusively the C3-methylated product, while using MeOTs gives exclusively the N-methylated product. The N-alkylated products show evidence of stereodynamic behavior in their NMR spectra. |
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| Keywords: | 1-Benzazepine Regioselective Alkylation Stereodynamic |
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