Expanded Chemistry of Formamidine Ureas

Organic Letters

Volumn 6, Issue 1, 2004, Pages 43-46

  Díaz, David D ^a   Finn, M G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FORMAMIDINE; ISOCYANIC ACID DERIVATIVE; THIOCARBAMIC ACID DERIVATIVE; UREA DERIVATIVE;

ACYLATION; ALKYLATION; ARTICLE; SUBSTITUTION REACTION;

EID: 0742269543     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035995f     Document Type: Article

References (50)

1. Ripka, A. S.; Díaz, D. D.; Sharpless, K. B.; Finn, M. G. Org. Lett. 2003, 5, 1531-1533.
2. Díaz, D. D.; Finn, M. G. Chem. Eur. J. In press.
3. Vincent, S.; Mons, S.; Lebeau, L.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 7527-7530.
4. (a) Nice, H. R. Org. React. 1962, 12, 57-100 and references therein.
5. (b) Tilles, H. J. Am. Chem. Soc. 1959, 81, 714-727.
6. (c) Ishikawa, K.; Okubo, I.; Kuwatsuka, S. Agr. Biol. Chem. 1973, 37, 165-173.
7. (d) Miyashita, Y.; Ohsako, H.; Takayama, C.; Sasaki, S. Quant. Struct.-Act. Relat. 1992, 11, 17-22.
8. (e) Cheng, H. M.; Hwang, D. F. Chem. Ecol. 1996, 12, 91-101.
9. (f) Rubin, B. Weed Crop Resistance Herbicides 1997, 39-50.
10. (g) Lindgren, B.; Lindgren, G.; Artursson, E.; Puu, G.; Fredriksson, J.; Andersson, M. J. Enzyme Inhib. 1985, 1, 1-11.
11. (h) Kochansky, J.; Feldmesser, J. J. Nematol. 1989, 21, 158-163.
12. (i) Kochansky, J.; Cohen, C. F. J. Agric. Entomol. 1990, 7, 293-304.
13. (j) Wachter, M. P. (Ortho Pharmaceutical Corp.). US Patent 4066681, 1978.
14. (k) Goel, A.; Mazur, S. J.; Fattah, R. J.; Hartman, T. L.; Turpin, J. A. ; Huang, M.; Rice, W. G.; Appella, E.; Inman, J. K. Bioorg. Med. Chem. Lett. 2002, 12, 767-770.
15. (a) Anbazhagan, M.; Rakeeb, A.; Deshmukh, A. S.; Rajappa, S. Tetrahedron Lett. 1998, 39, 3609-3612.
16. (b) Villemin, D.; Hachemi, M. L. M. Synth. Commun. 1996, 26, 2461-2471.
17. (c) Sebok, P.; Timar, T.; Eszenyl, T.; Patonay, T. J. Org. Chem. 1994, 59, 6318-6321.
18. (d) Bourne, N.; Williams, A.; Douglas, K. T.; Penkava, T. R. J. Chem. Soc., Perkin Trans. 2 1984, 1827-1832.
19. (e) Ewing, S. P.; Lockshon, D.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 3072-3084.
20. (a) Riemschneider, R.; Wojahn, F. Pharmazie 1949, 4, 460-462.
21. (b) Riemschneider, R. J. Am. Chem. Soc. 1956, 78, 844-847.
22. (c) Kochansky, J. P.; Wright, F. C. J. Economic Entomol. 1985, 78, 599-606.
23. (d) Isobe, T.; Ishikawa, T. J. Org. Chem. 1999, 64, 5832-5835.
24. (a) Newman, M. S.; Karnes, H. A. J. Org. Chem. 1966, 31, 3980-3984.
25. (b) Kwart, H.; Evans, E. R. J. Org. Chem. 1966, 31, 410-413.
26. (c) Beaulieu, F.; Snieckus, V. Synthesis 1992, 112-118.
27. (a) Eilingsfield, H.; Möbius, L. Chem. Ber. 1965, 98, 1293-1307.
28. (b) Walter, W.; Bode, K.-D. Angew. Chem., Int. Ed. Engl. 1967, 6, 281-293.
29. (a) Akiba, K.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1973, 13-14.
30. (b) Adamski, R. J.; Numajiri, S.; Poe, R.; Spears, L. J. J. Med. Chem. 1971, 14, 1244-1244.
31. Faissat, L.; Chavis, C.; Montéro, J.-L.; Lucar, M. J. Chem. Soc., Perkin Trans. 1 2002, 1253-1259.
32. Salvatore, R. N.; Sahab, S.; Jung, K. W. Tetrahedron Lett. 2001, 42, 2055-2058.
33. (a) Mizuno, T.; Nishiguchi, I.; Okushi, T.; Hiroshima, T. Tetrahedron Lett. 1991, 32, 6867-6868.
34. (b) Mizuno, T.; Kawanishi, A.; Nishiguchi, I.; Hirashima, T. Chem. Express 1991, 6, 997-1000.
35. Harusawa, S.; Osaki, H.; Fujii, H.; Yoneda, R.; Kurihara, T. Tetrahedron 1992, 48, 9433-9450.
36. Gais, H.-H.; Böhme, A. J. Org. Chem. 2002, 67, 1153-1161.
37. Reddy, T. I.; Bhawal, B. M.; Rajappa, S. Tetrahedron Lett. 1992, 33, 2857-2860.
38. (a) Grisley, D. W., Jr.; Stephens, J. A. J. Org. Chem. 1961, 26, 3568-3574.
39. (b) Jacob, J.; Reynolds, K. A.; Jones, W. D. Organometallics 2001, 20, 1028-1031.
40. (c) Mizuno, T.; Takahashi, J.; Ogawa, A. Tetrahedron 2003, 59, 1327-1331.
41. (d) Mizuno, T.; Nishiguchi, I. N.; Sonoda, N. Tetrahedron 1994, 50, 5669-5680.
42. (e) Koch, P. Tetrahedron Lett. 1975, 25, 2087-2088.
43. For examples of the reactivity of thiazolines, see: (a) Barton, M. A.; Kenner, G. W.; Sheppard, R. C. J. Chem. Soc. C 1966, 1061-1065. (b) Barrett, A. G. M.; Sturgess, M. A. J. Org. Chem. 1987, 52, 3940-3941. (c) Schmitz, W. D.; Romo, D. Tetrahedron Lett. 1996, 37, 4857-4860.
44. For examples of the reactivity of thiazolines, see: (a) Barton, M. A.; Kenner, G. W.; Sheppard, R. C. J. Chem. Soc. C 1966, 1061-1065. (b) Barrett, A. G. M.; Sturgess, M. A. J. Org. Chem. 1987, 52, 3940-3941. (c) Schmitz, W. D.; Romo, D. Tetrahedron Lett. 1996, 37, 4857-4860.
45. For examples of the reactivity of thiazolines, see: (a) Barton, M. A.; Kenner, G. W.; Sheppard, R. C. J. Chem. Soc. C 1966, 1061-1065. (b) Barrett, A. G. M.; Sturgess, M. A. J. Org. Chem. 1987, 52, 3940-3941. (c) Schmitz, W. D.; Romo, D. Tetrahedron Lett. 1996, 37, 4857-4860.
46. Almqvist, F.; Guillaume, D.; Hultgren, S. J.; Marshall, G. R. Tetrahedron Lett. 1998, 39, 2293-2294.
47. For preparation of enantiopure imidazolines, see: (a) Boland, N. A.; Casey, M.; Hynes, S. J.; Matthews, J. W.; Smyth, M. P. J. Org. Chem. 2002, 67, 3919-3922 and references therein., (b) Gust, R.; Keilitz, R.; Schimidt, K. J. Med. Chem. 2001, 44, 1963-1970.
48. For preparation of enantiopure imidazolines, see: (a) Boland, N. A.; Casey, M.; Hynes, S. J.; Matthews, J. W.; Smyth, M. P. J. Org. Chem. 2002, 67, 3919-3922 and references therein. (b) Gust, R.; Keilitz, R.; Schimidt, K. J. Med. Chem. 2001, 44, 1963-1970.
49. (a) Dey, P. D.; Sharma, A. K.; Rai, S. N.; Mahajan, M. P. Tetrahedron 1995, 51, 7459-7468.
50. (b) de Faria, A. R.; Matos, C. R. R.; Correia, C. R. D. Tetrahedron Lett. 2003, 34, 27-30.