Journal
SYNTHESIS-STUTTGART
Volume 46, Issue 10, Pages 1380-1388Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1341026
Keywords
N-alkylation; alcohol; theophylline; TsTh; DBU
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Funding
- Shiraz University of Technology Research Council
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A convenient and highly efficient one-pot N-alkylation of theophylline from alcohols via N-7-tosyltheophylline (TsTh) is described. In this protocol, the treatment of primary and/or secondary alcohols with a mixture of TsTh and 1,8-diazabicyclo[5.4.0]undec-7-ene in refluxing acetonitrile affords the corresponding N-7-alkyltheophylline in good to excellent yields; the reaction was optimized for solvent and base. This methodology is highly efficient for various structurally diverse primary and secondary alcohols. A plausible mechanism for the one-pot N-alkylation of theophylline with alcohols via TsTh has been suggested.
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