Rearrangement reactions; 14: Synthesis of functionalized thiazoles via attack of heteroatom nucleophiles on allenyl isothiocyanates

Synthesis

Volumn , Issue 17, 2005, Pages 2920-2926

  Banert, Klaus ^a   Al Hourani, Baker Jawabrah ^a   Groth, Stefan ^a   Vrobel, Kai ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Addition reactions; Allenes; Heterocycles; Isothiocyanates; Ring closure

Indexed keywords

ADDITION REACTIONS; AMINES; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ALLENES; HETEROCYCLES; ISOTHIOCYANATES; RING CLOSURE;

NITROGEN COMPOUNDS;

ALCOHOL; ALIPHATIC AMINE; ALLENE DERIVATIVE; AMIDE; AROMATIC AMINE; GUANIDINE DERIVATIVE; HYDROGEN SULFIDE; ISOTHIOCYANIC ACID; NITROGEN; OXYGEN; PHENOL; SODIUM HYDROXIDE; SULFUR; THIAZOLE; THIOPHENOL;

ADDITION REACTION; AQUEOUS SOLUTION; ARTICLE; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS;

EID: 27944453029     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872203     Document Type: Article

References (35)

1. Part 13: Banert, K.; Hagedorn, M.; Schlott, J. Chem. Lett. 2003, 32, 360.
2. (a) Banert, K.; Hückstädt, H.; Vrobel, K. Angew. Chem. 1992, 104, 72.
3. (b) Banert, K.; Hückstädt, H.; Vrobel, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 90.
4. (c) Banert, K.; Groth, S.; Hückstädt, H.; Lehmann, J.; Schlott, J.; Vrobel, K. Synthesis 2002, 1423.
5. (a) Billeter, O. Ber. Dtsch. Chem. Ges. 1875, 8, 462.
6. (b) Gerlich, G. Justus Liebigs Ann. Chem. 1875, 178, 80.
7. (c) Billeter, O. Helv. Chim. Acta 1925, 8, 337.
8. (d) Mumm, O.; Richter, H. Ber. Dtsch. Chem. Ges. 1940, 73, 843.
9. (e) DeWolfe, R. H.; Young, W. G. Chem. Rev. 1956, 56, 753 (see page 856).
10. (f) Smith, P. A. S.; Emerson, D. W. J. Am. Chem. Soc. 1960, 82, 3076.
11. (g) Iliceto, A.; Fava, A.; Mazzucato, U. Tetrahedron Lett. 1960, No. 11, 27.
12. (h) Emerson, D. W.; Klapprodt Booth, J. J. Org. Chem. 1965, 30, 2480.
13. (i) Fava, A. Org. Sulfur Compd. 1966, 2, 73.
14. (j) Ferrier, R. J.; Vethaviyaser, N. J. Chem. Soc. C 1971, 1907.
15. (k) Guthrie, R. D.; Williams, G. J. J. Chem. Soc., Chem. Commun. 1971, 923.
16. (l) Huber, S.; Stamouli, P.; Jenny, T.; Neier, R. Helv. Chim. Acta 1986, 69, 1898.
17. (m) Hansen, H.-J. Chimia 1999, 53, 163.
18. (n) Hansen, H.-J. Chimia 2000, 54, 105.
19. For reviews on the synthesis of thiazoles, see: (a) Kikelj, D.; Urleb, U. In Science of Synthesis, Vol. 11; Schaumann, E., Ed.; Thieme: Stuttgart, 2002, 627.
20. (b) Liebscher, J. In Houben-Weyl, Vol. E 8b/Part 2; Schaumann, E., Ed.; Thieme: Stuttgart, 1994, 4th ed, 1.
21. (c) Dondoni, A.; Merino, P. In Comprehensive Heterocyclic Chemistry II, Vol. 3; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1994, 373.
22. (d) Sharma, S. Sulfur Rep. 1989, 8, 327.
23. Bosco, M.; Forlani, L.; Liturri, V.; Riccio, P.; Todesco, P. E. J. Chem. Soc. B 1971, 1373.
24. Cornwell, S. P.; Kaye, P. T.; Kent, A. G.; Meakins, G. D. J. Chem. Soc., Perkin Trans. 1 1981, 2340.
25. (a) Forlani, L. Gazz. Chim. Ital. 1981, 111, 159.
26. (b) Erlenmeyer, H.; Herzfeld, L.; Prijs, B. Helv. Chim. Acta 1955, 38, 1291.
27. Eloy, F.; Deryckere, A. Chim. Ther. 1973, 8, 437.
28. Jansen, M.; Potschka, H.; Brandt, C.; Löscher, W.; Dannhardt, G. J. Med. Chem. 2003, 46, 64.
29. Gebhardt, W. Ber. Dtsch. Chem. Ges. 1884, 17, 2088.
30. Kolosova, M. O. Zh. Obshch. Khim. 1963, 33, 3667.
31. Organikum, 22. Ed.; Wiley-VCH: Weinheim, 2004, 647.
32. Austin, P. W. (Imperial Chemical Industries PLC) EP 244962, 1986; Chem. Abstr. 1988,108, P89483d.
33. Sachdev, H. S.; Dhami, K. S.; Atwal, M. S. Tetrahedron 1961, 14, 304.
34. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
35. Banert, K.; Groth, S.; Hückstädt, H.; Vrobel, K. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 95-96, 323.