The Role of Phase Transfer Catalysis in the Microwave-Assisted N-Benzylation of Amides, Imides and N-Heterocycles

Author(s): Istvan Greiner, Fanni Daruny Sypaseuth, Alajos Grun, Eva Karsai, Gyorgy Keglevich.

Journal Name: Letters in Organic Chemistry

Volume 6 , Issue 7 , 2009

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Abstract:

The effect of triethylbenzylammonium chloride (TEBAC) was studied on the outcome of the microwaveassisted solid-liquid phase N-alkylation of amides, imides and N-heterocycles using benzyl halides and K2CO3. It was found that while the benzylation of amides may be somewhat promoted by the presence of TEBAC, succinimide and benzimidazole are so reactive that there is no need to use the catalyst. At the same time, the outcome of the benzylation of phenothiazine may be significantly influenced by the presence or absence of TEBAC in respect of N- versus C-alkylation.

Keywords: N-alkylation, microwave, phase transfer catalysis, selectivity

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Article Details

VOLUME: 6
ISSUE: 7
Year: 2009
Page: [529 - 534]
Pages: 6
DOI: 10.2174/157017809789869546
Price: $65

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