A Fast and Parallel Route to Cyclic Isothioureas and Guanidines with Use of Microwave-Assisted Chemistry

Journal of Organic Chemistry

Volumn 69, Issue 5, 2004, Pages 1571-1580

  Sandin, Helena ^a   Swanstein, Marie Louise ^a   Wellner, Eric ^a  

^a Box 724 ^*  (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; DERIVATIVES; MICROWAVES;

MICROWAVE-ASSISTED CHEMISTRY; NUCLEOPHILICITY; PARALLEL ROUTES;

ORGANIC COMPOUNDS;

GUANIDINE DERIVATIVE; THIOUREA DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; CYCLIZATION; DERIVATIZATION; METHODOLOGY; MICROWAVE RADIATION; ORGANIC CHEMISTRY; REACTION ANALYSIS; SOLUBILITY; SYNTHESIS; THERMAL ANALYSIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; GUANIDINES; ISOTHIURONIUM; MICROWAVES; MOLECULAR STRUCTURE; THIOUREA;

EID: 1442275502     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030338m     Document Type: Article

References (47)

1. (a) Kienzle, F.; Kaiser, A.; Madhukar, S. C. Eur. Med. Chem. 1982, 17, 547.
2. (b) Weinhardt, K.; Wallach, M. B.; Marx, M. J. Med. Chem. 1985, 28, 694.
3. (c) Laufer, S. A.; Striegel, H.-G.; Wagner, G. K. J. Med. Chem. 2002, 45, 4695.
4. (d) Rockway, T. W. Expert Opin. Ther. Pat. 2003, 13, 773.
5. (e) Chiron Corp. Expert Opin. Ther. Pat. 2003, 13, 551.
6. (f) Donnelly, L. E.; Rogers, D. F. Expert Opin. Ther. Pat. 2003, 13, 1345.
7. (g) Lehmann, J.; Rob, B. Liebigs Ann. Chem. 1994, 805.
8. (a) Unger Liebigs Ann. Chem. 1846, 59, 69.
9. (b) Heintz Ann. Phys. 1848, 74, 133.
10. (c) Hofmann, A. W. Liebigs Ann. Chem. 1948, 67, 131.
11. (d) Beilstein; Geuther Liebigs Ann. Chem. 1858, 108, 94.
12. (e) Maly Z. Chem. 1869, 259.
13. (f) Rathke, B. Ber. Dtsch. Chem. Ges. 1881, 14, 1774.
14. (a) Katritzky, A. R.; Cai, X.; Rogovoy, B. V. J. Comb. Chem. 2003, 5, 392.
15. (b) Woo, J. C. S.; MacKay, D. B. Tetrahedron Lett. 2003, 44, 2881.
16. (c) Summary of guanylation and guanidinylation methods: Powell, D. A.; Ramsden, P. D.; Batey, R. A. J. Org. Chem. 2003, 68, 2300.
17. (d) Luthin, D. R.; Anderson, M. B. Bioorg. Med. Chem. Lett. 2002, 12, 3467.
18. (e) Moroni, M.; Koksch, B.; Osipov, S. N.; Crucianelli, M.; Frigerio, M. ; Bravo, P.; Burger, K. J. Org. Chem. 2001, 66, 130.
19. Marmillon, C.; Bompart, J.; Calas, M.; Escale, R.; Bonnet, P.-A. Heterocycles 2000, 53, 1317.
20. Mikolajczyk, M.; Kielbasinski, P. Tetrahedron 1981, 37, 233.
21. Lindström, P.; Tierney, J.; Wathey, B.; Westman, J. Tedrahedron 2091, 57, 9225.
22. Bretherick's Handbook of Reactive Chemical Hazards, 5th ed.; Butterworth-Heinemann: Boston, MA, 1995; Compound No. 4294.
23. Sampson, D. F. J.; Simmonds, R. G.; Bradley, M. Tetrahedron Lett. 2001, 42, 5517.
24. (a) Ahlbrecht, H.; Kornetzki, D. Synthesis 1988, 775.
25. (b) Ahlbrecht, H.; Schmitt, C.; Kornetzki, D. Synthesis 1991, 637.
26. (c) Matsumura, N.; Konishi, T.; Hayashi, H.; Yasui, M.; Iwasaki, F.; Mizuno, K. J. Heterocycl. Chem. 2002, 39, 189.
27. (a) Ferris, A. F.; Schutz, B. A. J. Org. Chem. 1963, 28, 71.
28. (b) Blonty, G. Liebigs Ann. Chem. 1982, 1927.
29. 2 under the same conditions, only the oxazolidinethionels13 was isolated. This indicates that the six-memberedring system is less favored. The formation of 6f can be explained by the higher nucleophilicity of nitrogen compared to oxygen.
30. Eichel, H. J.; Meyer, R. J.; Buzzi, P. F. J. Med. Chem. 1967, 10, 942.
31. Li, G.; Ohtani, T. J. Heterocycl. Chem. 1997, 45, 2471.
32. (a) Wilson, B. J. Chem. Soc. 1955, 1389.
33. (b) Van Allan J. Org. Chem. 1956, 21, 24.
34. (c) Lantos, L.; Gombatz, K.; McGuire, M.; Pridgen, L.; Remich, J.; Shilcrat, S. J. Org. Chem. 1988, 53, 4223
35. (d) Wei, J.; Liu, H.; Dick, A. R.; Yamamoto, H.; He, Y.; Waldeck, D. J. Am. Chem. Soc. 2002, 124, 9591.
36. Norman, R. O. C.; Coxon, J. M. Principles of Organic Synthesis, 3rd ed.; Nelson Thornes: Cheltenham, UK, 2001; p 107.
37. (a) Augustin, M.; Richter, M.; Salas, S. J. Prakt. Chem 1980, 322, 55.
38. (b) Effenberger, F.; Beisswenger, T.; Dannenhauer, F. Chem. Ber. 1988, 121, 2209.
39. Birtwell, S.; Curd, F. H. S.; Hendry, J. A.; Rose, F. L. J. Chem. Soc. 1948, 30, 1645.
40. The same calculations in water gave a somewhat less pronounced difference of 2.40 kcal/mol.
41. Ishikawa, F.; Kosayana, A.; Nakamura, S.; Kono, T. Chem. Pharm. Bull. 1978, 26, 3657.
42. Weinhardt, K.; Wallach M. B.; Marx, M. J. Med. Chem. 1985, 28, 694.
43. (a) McKay, A. F.; Hatton, W. G. J. Am. Chem. Soc. 1956, 78, 1618.
44. (b) Esser, F.; Pook, K. H.; Carpy, A.; Leger, J. M. Synthesis 1994, 1, 77.
45. Booth, R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882.
46. Ramalingam, K.; Raju, N.; Nanjappan, P.; Nowotnik, D. P. Tetrahedron 1995, 51, 2875.
47. Brown, H. C.; Narashimhan, S.; Choi, Y. M. Synthesis 1981, 37, 233.