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Synthesis 2014; 46(10): 1380-1388
DOI: 10.1055/s-0033-1341026
paper
© Georg Thieme Verlag Stuttgart · New York

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

Mohammad Navid Soltani Rad*
Department of Chemistry, Shiraz University of Technology, Shiraz 71555-313, Iran   Fax: +98(711)7354520   Email: soltani@sutech.ac.ir   Email: behrouz@sutech.ac.ir
,
Somayeh Behrouz*
Department of Chemistry, Shiraz University of Technology, Shiraz 71555-313, Iran   Fax: +98(711)7354520   Email: soltani@sutech.ac.ir   Email: behrouz@sutech.ac.ir
,
Hosnieh Najafi
Department of Chemistry, Shiraz University of Technology, Shiraz 71555-313, Iran   Fax: +98(711)7354520   Email: soltani@sutech.ac.ir   Email: behrouz@sutech.ac.ir
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Publication History

Received: 21 December 2013

Accepted after revision: 25 February 2014

Publication Date:
25 March 2014 (online)

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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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