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Synthesis 2002(2): 0172-0174
DOI: 10.1055/s-2002-19795
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© Georg Thieme Verlag Stuttgart · New York

A Convenient Method for the Synthesis of N-Vinyl Derivatives of Nucleobases

Renato Dalpozzoa, Antonio De Ninoa, Loredana Maiuoloa, Antonio Procopio*a, Roberto Romeob, Giovanni Sindonaa
a Dipartimento di Chimica, Università della Calabria, Arcavacata di Rende (CS), Italy
Fax: +39(98)4492055; e-Mail: procopio@unical.it;
b Dipartimento Farmaco-Chimico, Università di Messina, Messina, Italy
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Publication History

Received 12 October 2001
Publication Date:
03 August 2004 (online)

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Abstract

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) reveals, one more time, its enormous flexibility as Lewis acid catalyst, transforming the well known, but drastic, exchange of the acetyl group of vinyl acetate with pyrimidine and purine derivatives in a very gentle and quick method to obtain a whole set of vinyl nucleobases.

Key words

trimethylsilyl trifluoromethanesulfonate - nucleobases - alkene complexes - Lewis acids - vinyl nucleobases