Thiazole as leaving group. Thermal elimination from thiazolylketoses

Heterocycles

Volumn 50, Issue 1, 1999, Pages 419-426

  Dondoni, Alessandro ^a   Marra, Alberto ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

KETOSE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; TEMPERATURE SENSITIVITY; THERMOSTABILITY;

EID: 0032856695     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-98-8154     Document Type: Article

References (46)

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11. More complex catalysts have been also prepared in which the thiazolium ring is attached to various substrates, such as: a) chiral moieties (J. C. Sheehan, and T. Hara, J. Org. Chem., 1974, 39, 1196; W. Tagaki, Y. Tamura, and Y. Yano, Bull. Chem. Soc. Jpn., 1980, 53, 478; F. J. Leeper and D. H. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1995, 861);
12. More complex catalysts have been also prepared in which the thiazolium ring is attached to various substrates, such as: a) chiral moieties (J. C. Sheehan, and T. Hara, J. Org. Chem., 1974, 39, 1196; W. Tagaki, Y. Tamura, and Y. Yano, Bull. Chem. Soc. Jpn., 1980, 53, 478; F. J. Leeper and D. H. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1995, 861);
13. More complex catalysts have been also prepared in which the thiazolium ring is attached to various substrates, such as: a) chiral moieties (J. C. Sheehan, and T. Hara, J. Org. Chem., 1974, 39, 1196; W. Tagaki, Y. Tamura, and Y. Yano, Bull. Chem. Soc. Jpn., 1980, 53, 478; F. J. Leeper and D. H. C. Smith, J. Chem. Soc., Perkin Trans. 1, 1995, 861);
14. b) cylodextrin (R. Breslow and E. Kool, Tetrahedron Lett., 1988, 29, 1635);
15. c) cyclophane (F. Diederich and H.-D Lutter, Angew. Chem., Int. Ed. Engl., 1986, 25, 1125; F. Diederich and H.-D Lutter, J. Am. Chem. Soc., 1989, 111, 8438; S.-W. Tam-Chang, L. Jimenez, and F. Diederich, Helv. Chim. Acta, 1993, 76, 2616).
16. c) cyclophane (F. Diederich and H.-D Lutter, Angew. Chem., Int. Ed. Engl., 1986, 25, 1125; F. Diederich and H.-D Lutter, J. Am. Chem. Soc., 1989, 111, 8438; S.-W. Tam-Chang, L. Jimenez, and F. Diederich, Helv. Chim. Acta, 1993, 76, 2616).
17. c) cyclophane (F. Diederich and H.-D Lutter, Angew. Chem., Int. Ed. Engl., 1986, 25, 1125; F. Diederich and H.-D Lutter, J. Am. Chem. Soc., 1989, 111, 8438; S.-W. Tam-Chang, L. Jimenez, and F. Diederich, Helv. Chim. Acta, 1993, 76, 2616).
18. (a) R. Breslow and R. Kim, Tetrahedron Lett., 1994, 35, 699;
19. (b) Y.-T. Chen, G. L. Barletta, K. Haghjoo, J. T. Cheng, and F. Jordan, J. Org. Chem., 1994, 59, 7714;
20. (c) A. Miyashita, Y. Suzuki, M. Kobayashi, N. Kuriyama, and T. Higashino, Heterocycles, 1996, 43, 509.
21. J. H. Teles, J.-P. Melder, K. Ebel, R. Schneider, E. Gehrer, W. Harder, S. Brode, D. Enders, K. Breuer, and G. Raabe, Helv. Chim. Acta, 1996, 79, 61 and references cited therein.
22. For a review see: H. Stetter, Angew. Chem., Int. Ed. Engl., 1976, 15, 639. An application of the Stetter reaction by the use of a polymer-supported thiazolium salt has been described, see: C. S. Sell and L. A. Dorman, J. Chem. Soc., Chem. Commun., 1982, 629.
23. For a review see: H. Stetter, Angew. Chem., Int. Ed. Engl., 1976, 15, 639. An application of the Stetter reaction by the use of a polymer-supported thiazolium salt has been described, see: C. S. Sell and L. A. Dorman, J. Chem. Soc., Chem. Commun., 1982, 629.
24. A. Dondoni, A. W. Douglas, and I. Shinkai, J. Org. Chem., 1993, 58, 3196.
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26. A. J. Arduengo, J. R. Goerlich, and W. J. Marshall, Liebigs Ann./Recueil, 1997, 365.
27. Obviously a facile release of benzothiazolium 2-ylide occurs also from 2-hydroxyalkylbenzothiazolium salts under mild base catalysis. Chikashita and coworkers have exploited the formation of this ylide to convert esters into ketones. See: (a) H. Chikashita, M. Ishihara, and K. Itoh, Heterocycles, 1985, 23, 2467;
28. (b) H. Chikashita, M. Ishihara, K. Takigawa, and K. Itoh, Bull. Chem. Soc. Jpn., 1991, 64, 3256.
29. (a) A. Dondoni and M.-C. Scherrmann, Tetrahedron Lett., 1993,34, 7319;
30. (b) A. Dondoni and M.C. Scherrmann, J. Org. Chem., 1994, 59, 6404.
31. Although 2-lithiothiazole is more conveniently prepared from 2-bromothiazole as described in ref. 13b, the same reagent can be also obtained from unsubstituted thiazole (3) as shown in Scheme 1.
32. A. Dondoni and A. Marra, Tetrahedron Lett., 1993, 34, 7327.
33. 13C NMR spectra (downfield chemical shifts have been observed for the ketofuranose anomers having the C-1-O-1 and C-2-O-2 bonds in a trans orientation; see: refs. 13b and 25, and A. Boschetti, L. Panza, F. Ronchetti, G. Russo, and L. Toma, J. Chem. Soc., Perkin Trans. 1, 1988, 3353). The major product resulted to be the α anomer, identical to the compound obtained by silylation of 1a . Thus, the compound isolated by Csuk and Schaade appears not to be 5 but the β anomer.
34. 13C NMR spectra (downfield chemical shifts have been observed for the ketofuranose anomers having the C-1-O-1 and C-2-O-2 bonds in a trans orientation; see: refs. 13b and 25, and A. Boschetti, L. Panza, F. Ronchetti, G. Russo, and L. Toma, J. Chem. Soc., Perkin Trans. 1, 1988, 3353). The major product resulted to be the α anomer, identical to the compound obtained by silylation of 1a . Thus, the compound isolated by Csuk and Schaade appears not to be 5 but the β anomer.
35. As expected from the results in ref. 12, the conversion of 9 and 10 into 4-phenylcyclohexanone was achieved through their W-methylthiazolium triflates. The removal of the thiazole ring as the 2-ylide from these salts occurred at it in 30 min upon treatment with 1 equiv. of DBU. On the other hand, without the addition of base the thermal elimination of the thiazole moiety was not observed after 20 h at 120 °C. It is worth noting that N-methylthiazolium triflates of 1a and 1d afforded quantitatively the corresponding lactones (2a) and (2d) by heating at 130 °C for only 15 min.
36. The attempts to trap the ylide (17) with an electrophile by performing the thermal elimination in neat benzaldehyde were unsuccessful.
37. A less stable protonated ketone or aldehyde has to be generated, along with the ylide (17), if an analogous reaction pathway is followed by tertiary or secondary alcohols such as 9-13.
38. a (glucose) = 12.4).
39. Compounds (9) and (10) were recovered unchanged after heating at 120 °C for 20 h in the presence of 3 equiv. of acetic acid.
40. D. D. Perrin and W. L. F. Armarego, "Purification of Laboratory Chemicals," 3rd ed., Pergamon Press, Oxford, 1988.
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42. V. Bertolasi, (University of Ferrara, Italy), private communication. The atomic coordinates for (9) and (11) have been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2, 1EZ, UK.
43. A. Dondoni, A. Marra, I. Rojo, and M.-C. Scherrmann, Tetrahedron, 1996, 52, 3057.
44. A. Dondoni, P. Perrone, and P. Merino, J. Org. Chem., 1995, 60, 8074.
45. A. Dondoni, A. Boscarato, P. Formaglio, J.-P. Bégué, and F. Benayoud, Synthesis, 1995, 654.
46. H. Zinner, E. Wittenburg, and G. Rembarz, Chem. Ber., 1959, 92, 1614.