Regio-and stereoselective synthesis of thiazole-substituted histamine and adenine derivatives by nucleophilic attack at allenyl isothiocyanate

Heterocycles

Volumn 75, Issue 11, 2008, Pages 2667-2679

  Al Hourani, Baker Jawabrah ^a   Banert, Klaus ^a   Rüffer, Tobias ^a   Walfort, Bernhard ^a   Lang, Heinrich ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79751471818     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-08-11430     Document Type: Review

References (37)

1. J. Sirois, G. Ménard, A. S. Moses, and E. Y. Bissonnette, J. Immunol., 2000, 164, 2964;
2. D. T. Davies, Aromatic Heterocyclic Chemistry, Oxford University Press, New York, 1992, p. 20;
3. R. Jain and L. A. Cohen, Tetrahedron, 1996, 52, 5363;
4. P. W. Baures, K. Kaliyan and J. Desper, Molecules, 2002, 7, 813.
5. C. E. S. Alvaro and N. S. Nudelman, J. Phys. Org. Chem., 2005, 18, 880.
6. D. Voet, J. G. Voet, and C. W. Pratt, Lehrbuch der Biochemie (ed. by A. G. Beck-Sickinger and U. Hahn), Wiley-VCH, Weinheim, 2002, p. 45;
7. T. W. G. Solomons and C. B. Fryhle, Organic Chemistry, 7th ed., Wiley, New York, 2000, p. 644.
8. M. Dreyfus, G. Dodin, O. Bensaude, and J. E. Dubois, J. Am. Chem. Soc., 1975, 97, 2369;
9. M.-T. Chenon, R. J. Pugmire, D. M. Grant, R. P. Panzica, and L. B. Townsend, J. Am. Chem. Soc., 1975, 97, 4636.
10. N. J. Leonard and T. R. Henderson, J. Am. Chem. Soc., 1975, 97, 4990.
11. N. Bodor, M. J. S. Dewar, and A. J. Harget, J. Am. Chem. Soc., 1970, 92, 2929;
12. F. Jordan and H. D. Sostman, J. Am. Chem. Soc., 1972, 94, 7898.
13. M. Rasmussen and J. M. Hope, Aust. J. Chem., 1982, 35, 525.
14. A. C. Bajji and D. R. Davis, J. Org. Chem., 2002, 67, 5352;
15. J. Wang and A. Gossauer, Helv. Chim. Acta, 1994, 77, 533;
16. M. D. García, O. Caamaño, F. Fernández, C. López, and E. De Clercq, Synthesis, 2005, 925.
17. E. P. Lira and C. W. Huffman, J. Org. Chem., 1966, 31, 2188.
18. M. Rasmussen and N. J. Leonard, J. Am. Chem. Soc., 1967, 89, 5439;
19. N. J. Leonard and J. A. Deyrup, J. Am. Chem. Soc., 1962, 84, 2148.
20. C. C. Price, G. M. Gaucher, P. Koneru, R. Shibakawa, J. R. Sowa, and M. Yamaguchi, Biochim. Biophys. Acta, 1968, 166, 327.
21. K. Banert, H. Hückstädt, and K. Vrobel, Angew. Chem., 1992, 104, 72;
22. K. Banert, H. Hückstädt, and K. Vrobel, Angew. Chem., Int. Ed. Engl., 1992, 31, 90;
23. K. Banert, Liebigs Ann./Recueil, 1997, 2005.
24. K. Banert, S. Groth, H. Hückstädt, J. Lehmann, J. Schlott, and K. Vrobel, Synthesis, 2002, 1423;
25. K. Banert, B. Jawabrah Al-Hourani, S. Groth, K. Vrobel, Synthesis 2005, 2920.
26. For reviews on the synthesis of thiazoles, see: D. Kikelj and U. Urleb, in: Science of Synthesis, Vol. 11 (ed. by E. Schaumann), Thieme, Stuttgart, 2002, pp. 627-833;
27. J. Liebscher, in: Houben-Weyl, 4th ed., Vol. E 8b/II (ed. by E. Schaumann), Thieme, Stuttgart, 1994, pp. 1-398;
28. A. Dondoni and P. Merino, in: Comprehensive Heterocyclic Chemistry II, Vol. 3 (ed. by A. R. Katritzky, C. W. Rees, and E. F. V. Scriven), Pergamon, Oxford, 1994, pp. 373-474;
29. S. Sharma, Sulfur Rep., 1989, 8, 327.
30. For the multi-step synthesis of products similar to 8 via classical Hantzsch procedure, see: P. V. Plazzi, F. Bordi, M. Mor, C. Silva, G. Morini, A. Caretta, E. Barocelli, and T. Vitali, Eur. J. Med. Chem., 1995, 30, 881.
31. For the reaction of 1 with isothiocyanates, see: C. R. Ganellin, S. K. Hosseini, Y. S. Khalaf, W. Tertiuk, J.-M. Arrang, M. Garbarg, X. Ligneau, and J.-C. Schwartz, J. Med. Chem., 1995, 38, 3342;
32. J. Isac-Garcia, F. Hernández-Mateo, F. G. Calvo-Flores, and F. Santoyo-González, J. Org. Chem., 2004, 69, 202.
33. 13
34. J. Emsley, D. J. Jones, and J. Lucas, Rev. Inorg. Chem., 1981, 3, 105.
35. W. C. Still, M. Kahn, and A. Mitra, J. Org. Chem., 1978, 43, 2923.
36. G. M. Sheldrick, Acta Crystallogr. Sect. A, 1990, 46, 467.
37. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, 1997.