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

Renato Dalpozzo; Antonio De Nino; Loredana Maiuolo; Antonio Procopio; Roberto Romeo; Giovanni Sindona

doi:10.1055/s-2002-19795

SHORTPAPER

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

Renato Dalpozzo^a, Antonio De Nino^a, Loredana Maiuolo^a, Antonio Procopio*^a, Roberto Romeo^b, Giovanni Sindona^a
^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

Abstract

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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

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References

1a Takemoto K. Inaki Y. Functional Monomers and Polymers: Procedure, Synthesis, Application M. Dekker; New York: 1987. p.149

1b Yashima E. Tajima T. Miyauchi N. Biopolymers 1992, 32: 811

1c Zhou J. Shevlin PB. Synth. Commun. 1997, 27: 3591

2a Pan S. Amankulor NM. Zhao K. Tetrahedron 1998, 54: 6587

2b Gi HJ. Xiang Y. Schinazi RF. Zhao K. J. Org. Chem. 1997, 62: 88

2c Leggio A. Liguori A. Procopio A. Siciliano C. Sindona G. Tetrahedron Lett. 1996, 37: 1277

2d Leggio A. Liguori A. Procopio A. Siciliano C. Sindona G. Nucleosides Nucleotides 1997, 16: 1515

2e Chiacchio U. Corsaro A. Iannazzo D. Piperno A. Rescifina A. Romeo R. Romeo G. Tetrahedron Lett. 2001, 42: 1777

3a Ueda N. Kondo K. Kono M. Takemoto K. Imoto M. Makromol. Chem. 1968, 120: 13

3b Ciappetti P. Taddei M. Tetrahedron 1998, 54: 11305

4a Pitha J. Ts’O POP. J. Org. Chem. 1968, 33: 1341

4b Kaye H. Chang S.-H. Tetrahedron 1970, 26: 1369

4c Kaye H. Polymer Lett. 1969, 7: 1

5 Dalpozzo R. De Nino A. Maiuolo L. Procopio A. De Munno G. Sindona G. Tetrahedron 2001, 57: 4035

6a Vorbrüggen H. Krolikiewicz K. Bennua B. Chem. Ber. 1981, 114: 1234

6b Vorbrüggen H. Höfle G. Chem. Ber. 1981, 114: 1256

6c Emde E. Domsch D. Feger H. Frick U. Götz A. Hergott HH. Hofmann K. Kober W. Krägeloth K. Oesterle T. Steppan W. West W. Simchen G. Synthesis 1982, 1