A Facile Access to Imidazo[2,1-b]thiazole and Thiazolo[3,2-a]pyrimidine Derivatives

Cyrille Landreau; David Deniaud; Alain Reliquet; Jean Claude Meslin

doi:10.1055/s-2001-17718

PAPER

A Facile Access to Imidazo[2,1-b]thiazole and Thiazolo[3,2-a]pyrimidine Derivatives

Cyrille Landreau, David Deniaud*, Alain Reliquet, Jean Claude Meslin
Laboratoire de Synthèse Organique, UMR CNRS 6513, Faculté des Sciences et des Techniques, 2, Rue de la Houssinière, BP 92208, 44322 Nantes Cedex 03, France
Fax: +33(2)51125402; e-Mail: david.deniaud@chimie.univ-nantes.fr;

Abstract

Alle Artikel dieser Rubrik

Abstract

A new and efficient method for the synthesis of 2,3-dihydroimidazo[2,1-b]thiazoles 3, 2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-5-ones 4 and 2,3-dihydro-5H-thiazolo[3,2-a]pyrimidines 5 has been developed. The reactions of N′-(4,5-dihydrothiazol-2-yl)-N,N-dimethylamidines 1 with α-halogenoketones, acid chlorides or acrylic dienophiles were performed, leading to the title products.

Keywords

bicyclic compounds - heterocycles - acylations - alkylations - Diels-Alder reactions

Volltext

Referenzen

References

1 See: Devlin JP. Hargrave KD. Tetrahedron 1989, 45: 4327

For examples:

2a Leysen JE. Van Gompel P. Gommeren W. Woestenborghs R. Janssen PAJ. Psychopharmacology 1986, 88: 434

2b Claudi F. Scoccia L. Giorgioni G. Marucci G. Di Stephano A. Gessi S. Siniscalchi A. Andrea Borea P. Eur. J. Med. Chem. 1998, 33: 705

2c Van Laar M. Volkerts E. Verbaten M. Psychopharmacology 2001, 154: 189

3a Andreani A. Rambaldi M. Leoni A. Locatelli A. Andreani F. Gehret J.-C. Pharm. Acta Helv. 1996, 71: 247

3b Andreani A. Leoni A. Rambaldi M. Locatelli A. Bossa R. Galatulas I. Chiericozzi M. Bissoli M. Eur. J. Med. Chem. 1997, 32: 151

3c Andreani A. Leoni A. Locatelli A. Morigi R. Rambaldi M. Recanatini M. Garaliene V. Bioorg. Med. Chem. 2000, 8: 2359

3d Andreani A. Rambaldi M. Leoni A. Morigi R. Locatelli A. Giorgi G. Lenaz G. Ghelli A. Degli Esposti M. Eur. J. Med. Chem. 1999, 34: 883

4 Shilcrat SC. Hill DT. Bender PE. Griswold DE. Baures PW. Eggleston DS. Lantos I. Pridgen LN. J. Heterocycl. Chem. 1991, 28: 1181

5 Sisko J. Kassick AJ. Shetzline SB. Org. Lett. 2000, 2: 2877

6 Danel K. Pedersen EB. Nielsen C. J. Med. Chem. 1998, 41: 191

7a Tozkoparan B. Ertan M. Krebs B. Läge M. Kelicen P. Demirdamar R. Arch. Pharm. 1998, 331: 201

7b Tozkoparan B. Ertan M. Kelicen P. Demirdamar R. Farmaco 1999, 54: 588

8 See: Kappe CO. Roschger P. J. Heterocycl. Chem. 1989, 26: 55

For examples:

9a Malei M. Krbavi A. Stanovnik B. J. Heterocycl. Chem. 1997, 34: 49

9b Kutyrev A. Kappe T. J. Heterocycl. Chem. 1999, 36: 237

10 For an example: Meakins GD. Musk SRR. Robertson CA. Woodhouse LS. J. Chem. Soc., Perkin Trans. 1 1989, 643

11 O’Daly MA. Hopkinson CP. Meakins GD. Raybould AJ. J. Chem. Soc., Perkin Trans. 1 1991, 855

Most recent papers:

12a Friot C. Reliquet A. Reliquet F. Meslin JC. Synthesis 2000, 5: 695

12b Landreau C. Deniaud D. Reliquet F. Reliquet A. Meslin JC. Heterocycles 2000, 53: 2667

12c Landreau C., Deniaud D., Reliquet A., Reliquet F., Meslin J. C.; J. Heterocycl. Chem.; 2001, 38: 93.

12d Charrier J.-D. Landreau C. Deniaud D. Reliquet A. Reliquet F. Meslin JC. Tetrahedron 2001, 57: 4195

13 Richter R. Ulrich H. Chem. Ber. 1970, 103: 3525

14a Sakamoto M. Miyazawa K. Tomimatsu Y. Chem. Pharm. Bull. 1976, 24: 2532

14b Bogdanowicz-Szwed K. Krasodomska M. Monatsch. Chem. 1996, 127: 1273

15 Sakamoto M. Miyazawa K. Tomimatsu Y. Chem. Pharm. Bull. 1977, 25: 3360

16 Stanovnik B. Svete J. Synlett 2000, 8: 1077

17a Iwata C. Watanabe M. Okamoto S. Fujimoto M. Sakae M. Katsurada M. Imanishi T. Synthesis 1988, 261

17b Tanaka T. Iwata C. J. Synth. Org. Chem. Jpn. 1998, 56: 182

18 Vogel AI. A Text-book of Practical Organic Chemistry Longman; London: 1959. p.372

19 Brown GR. Dyson WR. J. Chem. Soc. C 1971, 1527

20 Shridhar DR. Jogibhukta M. Joshi PP. Rao CS. Junnarkar AY. Indian J. Chem., Sect. B 1984, 23: 492

21 Brown GR. J. Chem. Soc., Perkin Trans. 1 1973, 2022

22 Falch E. Natvig T. Acta Chem. Scand. 1970, 24: 1423

23 Fülöp F. Huber I. Szabó . Bernáth G. Sohár P. Tetrahedron 1991, 47: 7673