1,3-diaza-1,3-butadienes. Synthesis and conversion into pyrimidines by [4π + 2π] cycloaddition with electron deficient acetylenes. Synthetic utility of 2-(trichloromethyl)pyrimidines 1

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2470-2483

  Guzmán, Angel ^a   Romero, Moisés ^a,d   Talamás, Francisco X ^a   Villena, Rene ^b   Greenhouse, Robert ^c   Muchowski, Joseph M ^c  

^a Division de Investigación   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^c ROCHE BIOSCIENCE   (United States)

^d UNIVERSIDAD AUTÓNOMA DEL ESTADO DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIMIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029995229     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952106w     Document Type: Article

References (51)

1. Pinner, A. Chem. Ber. 1889, 22, 1600.
2. Pinner, A. Chem. Ber. 1890, 23, 2923.
3. Kunckell, F.; Bauer, R. Chem Ber. 1901, 34, 3029.
4. Ley, H.; Müller, F. Chem. Ber. 1907, 40, 2950.
5. Cooper, F. C.; Partridge, M. W.; Short, W. F. J. Chem. Soc. 1951, 391.
6. Peak, D. A. J. Chem. Soc. 1952, 215.
7. Tolmacheva, G. M.; Krukovskii, S. P.; Berman, E. L.; Ponamarenko, E. L. Izv. Akad. Nauk SSSR Ser. Khim. 1976, 1963; Chem. Abstr. 1977, 86, 88663c.
8. Tolmacheva, G. M.; Krukovskii, S. P.; Berman, E. L.; Ponamarenko, E. L. Izv. Akad. Nauk SSSR Ser. Khim. 1976, 1963; Chem. Abstr. 1977, 86, 88663c.
9. Boger, D. C.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987; pp 272-274.
10. (a) Crook, S.; Sykes, P. J. Chem. Soc., Perkin Trans. 1 1977, 1791.
11. (b) Mazumdar, S. N.; Ibnasud, I.; Mahajan, M. P. Tetrahedron Lett. 1986, 27, 5875.
12. (c) Mazumdar, S. N.; Sharma, M.; Mahajan, M. P. Tetrahedron Lett. 1987, 28, 2641.
13. (d) Luthardt, P.; Wurthwein, E.-W. Tetrahedron Lett. 1988, 29, 921.
14. (e) Barluenga, J.; Tomás, M.; Ballesteros, A.; López, L. A. Tetrahedron Lett. 1989, 30, 4573.
15. (f) Ibnasud, I.; Malar, E. J. P.; Sundaram, N. Tetrahedron Lett. 1990, 31, 7357
16. (g) Mazumdar, S. N.; Mahajan, M. P. Tetrahedron 1991, 47, 1473.
17. (h) Sain, B.; Singh, S. P.; Sandhu, J. S. Tetrahedron Lett. 1991, 32, 5151. Tetrahedron 1992, 48, 4567.
18. (h) Sain, B.; Singh, S. P.; Sandhu, J. S. Tetrahedron Lett. 1991, 32, 5151. Tetrahedron 1992, 48, 4567.
19. (i) Mazumdar, S. N.; Mukherjee, S.; Sharma, A. K.; Sengupta, D.; Mahajan, M. P. Tetrahedron 1994, 50, 7579.
20. In principle, a 1,3-diaza-1,3-butadiene bearing at least one hydrogen at position-4 and a leaving group at position-1 should also lead to pyrimidines with activated acetylenes. 1,4-Bis(dimethylamino)-2-phenyl-1,3-butadiene was synthesized for this purpose and found to not undergo cycloaddition with DMAD under a wide variety of neutral and acidic (Brønsted, Lewis) conditions (R. Greenhouse. Unpublished observations).
21. For a preliminary communication on these aspects of our studies, see: Guzmán, A.; Romero, M.; Talamás, F. X.; Muchowski, J. M. Tetrahedron Lett. 1992, 33, 3449.
22. Pielartzik, H.; Irmisch-Pielartzik, B.; Eicher, T. In Houben-Weyl, Methoden der Organischen Chimie; G. Theime: Stuttgart, 1985; Teil I, Vol. E5, pp 813-815.
23. Snytham, F. H.; Greth, W. E.; Langerman, N. R. J. Org. Chem. 1968, 34, 292. Mohashi. E.; Gordon, E. M. Synth. Commun. 1984, 14, 1159.
24. Snytham, F. H.; Greth, W. E.; Langerman, N. R. J. Org. Chem. 1968, 34, 292. Mohashi. E.; Gordon, E. M. Synth. Commun. 1984, 14, 1159.
25. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
26. Matsuda, I., Itoh, K.; Ishu, Y. J. Chem. Soc. (C) 1971, 1870.
27. Green, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis, 2nd ed ; J. Wiley & Sons Inc.: New York, 1991; pp 327-330.
28. 4 at 31°C, isobutylene has absorptions at δe; 1.68 and 4.63. Rumens, F. H. A.; Lomas, J. S.; Tiflon, B.; Coupry, C.; Lumbroso-Bader, N. Org. Magn. Reson. 1982, 19, 35.
29. It is noteworthy that the Boc-azadiene 24b is recovered unchanged after heating in xylenes for 6 h in the absence of DMAD.
30. Smith, P. A. S. In The Chemistry of Open Chain Nitrogen Compounds; W. A. Benjamin Inc.: New York, 1965; Vol. 1, p 163.
31. Chabrier, P.; Nachmias, G. Bull. Soc. Chim. Fr. 1950, D43-D65.
32. Eul, W.; Gattow, G. Z. Anorg. Allg. Chem. 1987, 545, 125.
33. 25
34. Burger, K.; Penninger, S. Synthesis 1978, 524.
35. a = 12.4; Albert, A.; Paal, B. Ibid.).
36. a = 12.4; Albert, A.; Paal, B. Ibid.).
37. a = 12.4; Albert, A.; Paal, B. Ibid.).
38. a = 12.4; Albert, A.; Paal, B. Ibid.).
39. Such addition products were also obtained in the cycloaddition reactions of the diazadienes 23, 31, and 33.
40. Kornblum, N.; Michel, R. E.; Kerber, R. C. J. Am. Chem. Soc. 1966, 88, 5660. Kornblum, N.; Davies, T. M.; Earl, G. W.; Holy, K. L.; Kerber, R. C.; Musser, M. T.; Snow, D. H. J. Am. Chem. Soc. 1967, 89, 725.
41. Kornblum, N.; Michel, R. E.; Kerber, R. C. J. Am. Chem. Soc. 1966, 88, 5660. Kornblum, N.; Davies, T. M.; Earl, G. W.; Holy, K. L.; Kerber, R. C.; Musser, M. T.; Snow, D. H. J. Am. Chem. Soc. 1967, 89, 725.
42. Cherkasov, V. N.; Dashevskaya, T. A. Ukr. Khim. Zh. 1973, 39, 1155; Chem. Abstr. 1974, 80, 47616x.
43. Cherkasov, V. N.; Dashevskaya, T. A. Ukr. Khim. Zh. 1973, 39, 1155; Chem. Abstr. 1974, 80, 47616x.
44. Chua, S.-W.; Cook, M. J.; Katritzky, A. R. J. Chem. Soc., Perkin Trans. 2 1974, 546.
45. Schaefer, F. C. J. Org. Chem. 1962, 27, 3608.
46. Goerdeler, J.; Porrmann, H. Chem. Ber. 1961, 94, 2856.
47. Marterstock, K.; Jensen, H. Ger. Patent 1.168,896,1964; Chem. Abstr. 1964, 61, 6991f. Jentzsch, W.; Seefedler, M. Chem. Ber. 1965, 98, 1342.
48. Marterstock, K.; Jensen, H. Ger. Patent 1.168,896,1964; Chem. Abstr. 1964, 61, 6991f. Jentzsch, W.; Seefedler, M. Chem. Ber. 1965, 98, 1342.
49. Marterstock, K.; Jensen, H. Ger. Patent 1.168,896,1964; Chem. Abstr. 1964, 61, 6991f. Jentzsch, W.; Seefedler, M. Chem. Ber. 1965, 98, 1342.
50. Bredereck, H.; Effenberger, F.; Hofmann, A. Chem. Ber. 1963, 96, 3265.
51. Cava, M. P.; Lakshmikanthan, M. V.; Mitchell, M. J. J. Org. Chem. 1969, 34, 2665.