Microwave-Assisted Synthesis
of 4-Amino-2-arylthieno[2,3-d]pyrimidines
and Their Subsequent Functionalization

Binbin Chen; Enrico Perspicace; Stéphanie Hesse; Gilbert Kirsch

doi:10.1055/s-0029-1218770

PAPER

Microwave-Assisted Synthesis of 4-Amino-2-arylthieno[2,3-d]pyrimidines and Their Subsequent Functionalization

Binbin Chen, Enrico Perspicace, Stéphanie Hesse*, Gilbert Kirsch
Laboratoire d’Ingénierie Moléculaire et Biochimie Pharmacologique, Institut Jean Barriol FR CNRS 2843, Université Paul Verlaine-Metz, 1 Boulevard Arago, 57070 Metz, France
Fax: +33(3)87315801; e-Mail: hesse@univ-metz.fr;

Abstract

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Abstract

New 4-amino-2-arylthieno[2,3-d]pyrimidines were synthesized by reacting 2-amino-3-cyanothiophenes and aryl nitriles under microwave irradiation. Functionalization of 4-amino group was made by acetic anhydride and several isocyanates.

Key words

2-amino-3-cyanothiophenes - 4-amino-2-arylthieno[2,3-d]pyrimidines - microwave irradiation

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References

1 Thomae D. Kirsch G. Seck P. Synthesis 2007, 1027

2 Thomae D. Kirsch G. Seck P. Kaminski T. Synthesis 2007, 2153

3 Hesse S. Perspicace E. Kirsch G. Tetrahedron Lett. 2007, 48: 5261

4 Perspicace E. Hesse S. Kirsch G. Yemloul M. Lecomte C. J. Heterocycl. Chem. 2009, 46: 459

5a Luke RWA. Ballard P. Buttar D. Campbell L. Curven J. Emery SC. Griffen AM. Hassall L. Hayter BR. Jones CD. McCoull W. Mellor M. Swain ML. Tucker JA. Bioorg. Med. Chem. Lett. 2009, 19: 6670

5b Luke RWA, Jones CD, McCoull W, and Hayter BR. inventors; WO Patent 2004013141.

6 Häcker H.-G. de la Haye A. Sterz K. Schnakenburg G. Wiese M. Gütschow M. Bioorg. Med. Chem. Lett. 2009, 19: 6102

7 Dai Y. Guo Y. Frey RR. Ji Z. Curtin ML. Ahmed AA. Albert DH. Arnold L. Arries SS. Barlozzari T. Bauch JL. Bouska JJ. Bousquet PF. Cunha GA. Glaser KB. Guo J. Li J. Marcotte PA. Marsh KC. Moskey MD. Pease LJ. Stewart KD. Stoll VS. Tapang P. Wishart N. Davidsen SK. Michaelides MR. J. Med. Chem. 2005, 48: 6066

8 Barnes DM. Haight AR. Hameury T. McLaughlin MA. Mei J. Tedrow JS. Dalla Riva Toma J. Tetrahedron 2006, 62: 11311

9a Taylor EC. Borror AL. J. Org. Chem. 1961, 26: 4967

9b Baker BR. Kozma JA. J. Med. Chem. 1968, 11: 656

10 Bhuiyan MMH. Rahman KMM. Hossain MK. Rahim MA. Hossain MI. Croat. Chem. Acta 2005, 78: 633

11 Seijas JA. Vasquez-Tato MP. Montserrat Martinez M. Tetrahedron Lett. 2000, 41: 2215

12 Da Settimo F. Primofiore G. La Motta C. Taliani S. Simorini F. Marini AM. Mugnaini L. Lavecchia A. Novellino E. Tuscano D. Martini C. J. Med. Chem. 2005, 50: 5162

13a Smith CJ. Iglesias-Sigüenza FJ. Baxendale IR. Ley SV. Org. Biomol. Chem. 2007, 5: 2758

13b Oliveira-Campos AMF. Sivasubramanian A. Rodrigues LM. Seijas JA. Vasquez-Tato MP. Peixoto F. Abreu CG. Cidade H. Oliveira AE. Pinto M. Helv. Chim. Acta 2008, 91: 1336

14a Shishoo CJ. Devani MB. Bhadti VS. Jain KS. Ananthan S. J. Heterocycl. Chem. 1990, 27: 119

14b Dave KG. Devani MB. Kalyanaraman R. Ananthan S.
J. Heterocycl. Chem. 1980, 17: 1497

15 Rahman KMM. Chowdhury AZMS. Bhuiyan MMH. Hossain MK. Uddin MK. Pak. J. Sci. Ind. Res. 2003, 46: 95

16 Bhuiyan MMH. Fakruddin M. Pak. J. Sci. Ind. Res. 2005, 48: 37

17 Rosowsky A. Papoulis AT. Queener SF. J. Med. Chem. 1997, 40: 3694

18 Taylor EC. Berger JG. J. Org. Chem. 1967, 32: 2376