N ⁷-Tosyltheophylline (TsTh): A Highly Efficient Reagent for the One-Pot Synthesis of N ⁷-Alkyltheophyllines from Alcohols

Abstract

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.

Key words

N-alkylation - alcohol - theophylline - TsTh - DBU

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