Microwave-Assisted Silylation-Amination of Uracil Acyclonucleosides to 4-Alkylamino-2(1H)-Pyrimidinone Analogues

Vincent Roy; Adam Mieczkowski; Dimitri Topalis; Sabine Berteina-Raboin; Dominique Deville-Bonne; Steven P. Nolan; Luigi A. Agrofoglio

doi:10.1055/s-2008-1067094

PAPER

Microwave-Assisted Silylation-Amination of Uracil Acyclonucleosides to 4-Alkylamino-2(1H)-Pyrimidinone Analogues

Vincent Roy^a, Adam Mieczkowski^a, Dimitri Topalis^b, Sabine Berteina-Raboin^b, Dominique Deville-Bonne^b, Steven P. Nolan^c, Luigi A. Agrofoglio*^a
^a Institut de Chimie Organique et Analytique, UMR 6005, Université d’Orléans, 45067 Orléans, France
Fax: +33(2)38417281; e-Mail: luigi.agrofoglio@univ-orleans.fr;
^b Laboratoire d’Enzymologie Moléculaire et Fonctionnelle, FRE CNRS 2852, Université Pierre & Marie Curie, 4 place Jussieu, 75005 Paris, France
^c Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain

Abstract

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Abstract

The synthesis of acyclic N⁴-substituted cytosine nucleoside phosphonates using a microwave-assisted N⁴-silylation-amination and olefin cross-metathesis as key assembly steps is described. The microwave-assisted silylation-amination is compared to a conventional heating protocol. While yields and purities of the coupling products were comparable under both conditions, microwave heating allows a significant acceleration of the reaction (from 48 h to 5 h).

Key words

microwaves - silylation-amination - olefin cross-metathesis - acyclic nucleoside phosphonates

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References

<A NAME="RZ06208SS-1A">1a</A> Simons C. Nucleoside Mimetics: Their Chemistry and Biological Properties, Advanced Chemistry Text Series Vol. 3: Gordon and Breach Science; Amsterdam: 2001. p.192

<A NAME="RZ06208SS-1B">1b</A> Agrofoglio LA. Challand SR. Acyclic, Carbocyclic and l -Nucleosides Kluwer Academic Publishers; Dordrecht: 1998.

<A NAME="RZ06208SS-2A">2a</A> Kinchington D. Balzarini J. De Clercq E. Daluge S. Field HJ. Int. Antivir. News 2000, 65: 2959

<A NAME="RZ06208SS-2B">2b</A> Agrofoglio LA. Amblard F. Broggi J. Garnier E. Modern Approaches to the Synthesis of O- and N-Heterocyles Vol. 2: Kaufman TS. Larghi EL. Research Signpost; Trivandrum India: 2007. p.195-246

<A NAME="RZ06208SS-3A">3a</A> Kanai T. Ichino M. Hoshi A. Kanzawa F. Kuretani K. J. Med. Chem. 1974, 17: 1076

<A NAME="RZ06208SS-3B">3b</A> Wempen I. Miller N. Falco EA. Fox JJ. J. Med. Chem. 1967, 10: 144

<A NAME="RZ06208SS-4A">4a</A> Wempen I. Duschinsky R. Kaplan L. Fox JJ. J. Am. Chem. Soc. 1961, 83: 4755

<A NAME="RZ06208SS-4B">4b</A> Pizer LI. Cohen SS. J. Biol. Chem. 1960, 235: 2387

<A NAME="RZ06208SS-5A">5a</A> De Clercq E. Biochem. Pharmacol. 2007, 73: 911

<A NAME="RZ06208SS-5B">5b</A> Ying C. Holy A. Hocková D. Havlas Z. De Clercq E. Neyts J. Antimicrob. Agents Chemother. 2005, 49: 1177

<A NAME="RZ06208SS-5C">5c</A> Naesens L. Lenaerts L. Andrei G. Snoeck R. Van Beers D. Holy A. Balzarini J. De Clercq E. Antimicrob. Agents Chemother. 2005, 49: 1010

<A NAME="RZ06208SS-5D">5d</A> Painter GR. Almond MR. Trost LC. Lampert BM. Neyts J. De Clercq E. Korba BE. Aldern KA. Beadle JR. Hostetler KY. Antimicrob. Agents Chemother. 2007, 51. 3505

<A NAME="RZ06208SS-6A">6a</A> Chalupová S. Hol A. Masojídková M. Collect. Czech. Chem. Commun. 2005, 12: 2066

<A NAME="RZ06208SS-6B">6b</A> Chalupová S. Hol A. Masojídková M. Collect. Czech. Chem. Commun. 2005, 12: 2053

<A NAME="RZ06208SS-7">7</A> Fox JJ. van Praag D. Wempen I. Doerc IL. Cheong L. Knoll JE. Edidinoff ML. Bendick A. Brown GB. J. Am. Chem. Soc. 1959, 81: 178

<A NAME="RZ06208SS-8A">8a</A> Sung WL. Nucleic Acids Res. 1981, 6: 6139

<A NAME="RZ06208SS-8B">8b</A> Matsuda AOK. Miyasaka T. Chem. Pharm. Bull. 1985, 33: 2575

<A NAME="RZ06208SS-8C">8c</A> Reese CB. Ubasawa A. Tetrahedron Lett. 1980, 21: 2265

<A NAME="RZ06208SS-8D">8d</A> Perbost M. Sanghvi YS. J. Chem. Soc., Perkin Trans. 1 1994, 2051

<A NAME="RZ06208SS-9">9</A> Nyilas A. Chattopadhyaya J. Acta Chem. Scand. B 1986, 40: 826

<A NAME="RZ06208SS-10">10</A> Lin T.-S. Mancini WR. J. Med. Chem. 1983, 26: 544

<A NAME="RZ06208SS-11A">11a</A> Dechaux E. Monneret C. Nucleosides Nucleotides 1999, 17: 1

<A NAME="RZ06208SS-11B">11b</A> Matsuda AY. Sasaki T. Ueda T. J. Med. Chem. 1991, 34: 999

<A NAME="RZ06208SS-12A">12a</A> Vorbrüggen H. Acc. Chem. Res. 1995, 28: 509

<A NAME="RZ06208SS-12B">12b</A> Vorbrüggen H. Krolikiewicz K. Niedballa U. Liebigs Ann. Chem. 1975, 988

<A NAME="RZ06208SS-12C">12c</A> Sako M. Kihara T. Kawada H. Hirota K. J. Org. Chem. 1999, 64: 9722

<A NAME="RZ06208SS-13">13</A> Loupy A. Microwaves in Organic Synthesis Wiley-VCH; Weinheim: 2002. and references cited therein

<A NAME="RZ06208SS-14A">14a</A> Agrofoglio LA. Nolan SP. Curr. Top. Med. Chem. 2005, 5: 1541

<A NAME="RZ06208SS-14B">14b</A> Amblard F. Nolan SP. Agrofoglio LA. Tetrahedron 2005, 61: 7067

<A NAME="RZ06208SS-14C">14c</A> Agrofoglio LA. Kumamoto H. Roy V. Chem. Today 2006, 24: 16

<A NAME="RZ06208SS-14D">14d</A> Kumamoto H. Topalis D. Broggi J. Pradère U. Roy V. Berteina-Raboin S. Nolan SP. Deville-Bonne D. Andrei G. Snoeck R. Garin D. Crance J.-M. Agrofoglio LA. Tetrahedron 2008, 64: 3517

<A NAME="RZ06208SS-15">15</A> Chatterjee AK. Choi T.-L. Sanders DP. Grubbs RH. J. Am. Chem. Soc. 2003, 125: 11360

<A NAME="RZ06208SS-16A">16a</A> Roy R. Das SK. J. Chem. Soc., Chem. Commun. 2000, 519

<A NAME="RZ06208SS-16B">16b</A> Phillips AJ. Abell AD. Aldrichimica Acta 1999, 32: 75

<A NAME="RZ06208SS-17">17</A> Hang J. Stevens ED. Nolan SP. Peterson JL. J. Am. Chem. Soc. 1999, 121: 8168