Synthesis and reactivity of N-selenoacylamidines precursors of selenoheterocycles

Tetrahedron

Volumn 54, Issue 11, 1998, Pages 2545-2562

  Purseigle, Franck ^a   Dubreuil, Didier ^a   Marchand, Anne ^a   Pradère, Jean Paul ^a   Goli, Martin ^c   Toupet, Loic ^b  

^a Centre National de la Recherche Scientifique   (France)

^b UMR 6626   (France)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; N SELENOACYLAMIDINE; SELENOHETEROCYCLE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032510330     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10440-9     Document Type: Article

References (78)

1. 1. Boger, D.L.; Weinreb S.M. "Hetero Diels-Alder Methodology in Organic Synthesis", 1987, Academic Press, San Diego.
2. 2. a) Boger, D.L. Comprehensive Organic Synthesis, 1991, Vol. 5, P.485 "Heterodiene Additions", Ed. Paquette L.A. Pergamon, Oxford, p.451.
3. 2. a) Boger, D.L. Comprehensive Organic Synthesis, 1991, Vol. 5, P.485 "Heterodiene Additions", Ed. Paquette L.A. Pergamon, Oxford, p.451.
4. b) Tschaen, D.M.; Twos, E.; Weinreb, S.M. J. Org. Chem., 1984,49, 5058.
5. c) Kober, R.; Papadopoulos, K.; Miltz, W.; Enders, D.; Steglich, W.; Reuter, H.; Puff, H. Tetrahedron, 1985, 41, 1693.
6. d) Scola, P.M.; Weinreb, S.M. J. Org. Chem., 1986, 51, 3248.
7. e) Melnick, M.J.; Weinreb, S.M. J. Org. Chem., 1988, 53, 850.
8. 3. a) Meslin, J.C.; Quiniou H. Bull. Soc. Chim. Fr., 1979, 7-8, 347.
9. b) Burger, K.; Huber, E.; Shöntag, W.; Ottlinger, R. J. Chem. Soc. Chem. Commun., 1983, p.945.
10. c) Pradère, J.P.; Roze, J.C.; Quiniou, H.; Danion-Bougot R.; Danion, D.; Toupet, L. Can. J. Chem., 1986, 64, 597.
11. d) Burger, K.; Huber, E.; Shöntag, W.; Partsht, H. Chemiker-Ztg., 1986, 110, 79.
12. e) Okazaki, R.; Masafumi, U.; Inamoto, N. Heterocycles, 1987, 25, 183.
13. f) Cellerin, C.; Tea, G. C; Pradere, J.P.; Guingant, A.; Guenot P. Sulfur Lett., 1988, 8, 205.
14. 4. Weinreb, S. M.; Scola, P. M.Chem. Rev., 1989, 89, 1525 and references therein.
15. 5. a) Chehna, M.; Pradère, J.P.; Quiniou, H.; Le Botlan, D.; Toupet, L. Phosphorus, Sulfur and Silicon, 1989, 42, 15.
16. b) Tea, G. C.; Pradère, J. P.; Quiniou, H. J. Org. Chem., 1985, 50, 1545.
17. c) Pradère, J.P.; Tonnard, F.; Abouelfida, A.; Cellerin, C.; Andriamanamihaja, M.; Jousseaume, B.; Toupet, L.; Guenot, P. Bull. Soc. Chim. Fr., 1993, 130, 610.
18. 6. a) Burger, K.; Ottlinger R. Tetrahedron Lett., 1978, 11, 973.
19. b) Burger, K.; Ottlinger, R.; Goth, H.; Firl, J. Chem. Ber., 1980, 113, 2699.
20. c) Okuma, K.; Kojima, K.; Kaneko, I.; Ohta, H. Tetrahedron Lett., 1992, 33, 1333.
21. d) Li, G.M.; Segi, M.; Nakajima T. Tetrahedron Lett., 1992, 33, 3515.
22. 7. a) Guziec Jr., F.S.; Moustakis, C. A. J. Org. Chem., 1984, 49, 189.
23. b) Fischer, H.; Gerbing, U.; Riede, J.; Benn, R. Angew. Chem., Int. Ed. Engl., 1986, 25, 78.
24. c) Okuma, K.; Sakata, J.I.; Tachibana, Y.; Honda, T.; Ohta, H. Tetrahedron Lett., 1987, 28, 6649.
25. d) Nakayama, J.; Akimoto, K.; Niijima, J.; Hoshino, M. Tetrahedron Lett., 1987, 28, 4423.
26. e) Okazaki, R.; Yuki R. Gosei Kagaku Kyokai Ski, 1988, 46, 1149.
27. f) Segi, M.; Takahashi, M.; Nakajima, T.; Suga, S. Tetrahedron Lett., 1988, 29, 6965.
28. g) Meinke, P.T.; Krafft, G.A. J. Am. Chem. Soc., 1988, 110, 8671. Ibid., 8679.
29. g) Meinke, P.T.; Krafft, G.A. J. Am. Chem. Soc., 1988, 110, 8671. Ibid., 8679.
30. h) Abelman, M.M. Tetrahedron Lett., 1991, 32, 7389.
31. i) Segi, M.; Kato, M.; Nakajima, T. Tetrahedron Lett., 1991, 32, 7427.
32. j) Shimada, K.; Jin, N.; Fujimura, M.; Nagano, Y.; Kudoh, E.; Takikawa, Y. Chem. Lett., 1992, p. 1843.
33. 8. Dubreuil, D.; Pradère, J.P.; Giraudeau, N.; Goli, M.; Tonnard, F. Tetrahedron Lett., 1995, 36, 237.
34. 9. a) Parnham, M. J. and Graf, E. Progress in Drug Research, 1991, Vol. 36, "Pharmacology of Synthetic Organic Selenium Compounds" Birkhäuser Verlag, Basel.
35. 9. a) Parnham, M. J. and Graf, E. Progress in Drug Research, 1991, Vol. 36, "Pharmacology of Synthetic Organic Selenium Compounds" Birkhäuser Verlag, Basel.
36. b) Klayman, D.I. Organic Selenium Compounds: Their Chemistry and Biology, 1983, "Synthetic Forms of Selenium and their Chemotherapeutic uses" Plenum Press, New York. Fodor, G. and Philips, B. A. The Chemistry of Organic Selenium and Tellurium Compounds, 1987,
37. b) Klayman, D.I. Organic Selenium Compounds: Their Chemistry and Biology, 1983, "Synthetic Forms of Selenium and their Chemotherapeutic uses" Plenum Press, New York. Fodor, G. and Philips, B. A. The Chemistry of Organic Selenium and Tellurium Compounds, 1987,
38. b) Klayman, D.I. Organic Selenium Compounds: Their Chemistry and Biology, 1983, "Synthetic Forms of Selenium and their Chemotherapeutic uses" Plenum Press, New York. Fodor, G. and Philips, B. A. The Chemistry of Organic Selenium and Tellurium Compounds, 1987,
39. 10. Vol. 2, Ed. Pataï, S. "Synthesis of Organic Conductors Containing Selenium and Tellurium", John Wiley & Sons, New york.
40. 11. The synthesis of N-selenoacylamidine 3a was previously described by Liebscher, J. et Al. in 30% yield from chloropropeniminium salt precursors. see Liebscher, J. Synthesis , 1988, p.655.
41. 12. a) Lai, L. L.; Reid, D.H. Synthesis, 1993, p.870.
42. b) Zhao, X.R.; Ruan, M.D.; Fan W.Q.; Zhou X.J. Synthetic Comm., 1994, 24, 1761.
43. 13. Shimada, K.; Hikage, S.; Takeishi, Y.; Takikawa, Y. Chem. Lett., 1990, p.1403.
44. 14. a) Weidinger, H.; Eilingsfeld, H. Belg. Patent 629972, 1963 : German Patent Application (DOS) 23.3, 1962 (Badische Anilin und Soda Fabrik A.G.); C.A., 1964, 61, 1803d.
45. 14. a) Weidinger, H.; Eilingsfeld, H. Belg. Patent 629972, 1963 : German Patent Application (DOS) 23.3, 1962 (Badische Anilin und Soda Fabrik A.G.); C.A., 1964, 61, 1803d.
46. b) Tea G. C.; Chehna, M.; Pradère, J.P.; Duguay, G.; Toupet, L. Phosphorus and Sulfur, 1986, 27, 327.
47. 15. Full details of the 3b X-ray structure determination have been deposited with the Cambridge Crystallographic Data Centre and can be obtained, on request, from the Director, 12 Union Road, Cambridge, CB2 1EZ, U.K..
48. 16. Paulmier, C. "Selenium Reagents and Intermediates in Organic Synthesis", 1986, Pergamon Press, Oxford.
49. 17. Toupet, L.; Pradère, J. P.; Bouzid, M.; Quiniou, H. Acta Cryst., 1989, C45, 1253.
50. 18. Tea, G. C.; Pradère, J. P.; Bujoli, B.; Quiniou, H.; Toupet, L. Bull. Soc. Chim. Fr., 1987, 1, 149.
51. 19. Anh, N. T. "Introduction à la chimie moleculaire", Ed. ellipses, 1994, p. 182.
52. 20. Liebscher, J.; Hartmann, H. Synthesis, 1976, p.521.
53. 21. For the preparation of 2-dialkylamino-selenazoles see: Liebscher, J.; Hartman, H. Z. Chem.,1976, 16, 18.
54. 22. Corey, E. J.; Chaykovsky, M. J. J. Am. Chem. Soc., 1965, 87, 1353.
55. 23. Toure, S.A.; Voglozin, A.; Degny, E.; Danion-Bougot, R.; Danion, D.; Pradère, J.P.; Toupet, L.; N'Guessan, Y.T. Bull. Soc. Chim. Fr., 1991, 128, 574.
56. 24. For action of diazomethane on N-thioacylamidine 2a see : Danion-Bougot, R.; Tuloup, R.; Danion, D.; Pradère, J. P.; Tonnard, F. Sulfur Lett., 1989, 9, 245.
57. 25. Purseigle, F.; Mann T. G.; Dubreuil, D.; Pradère, J. P.; Danion-Bougot, R.; Danion, D.; Toupet, L. To be submitted.
58. 26. Herail, M.; Purseigle, F.; Goli, M.; Dubreuil, D.; Pradère, J.P.; Proutière, A. J. Mol. Struct., 1996, 382, 39.
59. 27. Marchand, A.; Mauger, D.; Guingant, A.; Pradère, J.P. Tetrahedron Asymmetry, 1996, 6, 853.
60. 28. Tea, G. C.; Pradère J. P.; Quiniou, H. Synthetic Comm., 1986, 16, 79.
61. 29. Sauer, J.; Sustmann, R. Angew. Chem. Int. Ed. Engl., 1980, 79, 779.
62. 30. a) Fleming, I. in "Frontier Orbitals and Organic Chemical Reactions", J. Wiley & Sons, New York, 1975.
63. b) Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J. Am. Chem. Soc., 1986, 108, 7381 and references therein.
64. c) Anh., N. T. in "Orbitales Frontieres", 1995, InterEdition/ C.N.R.S Edition.
65. 31. Semi empirical PM3 calculations were carried out with SPARTAN software (4.0 version) on a Silicon Graphics Indy. For PM3 calculation see : Stewart, J. J. P. Comp. Chem., 1989, 42, 12.
66. 32. a) Heuzè, K.; Purseigle, F.; Dubreuil, D.; Pradère J. P. Synthetic Comm., 1997, in press.
67. b) Mann T. G.; Purseigle, F.; Dubreuil, D.; Pradère J. P.; Anh, N. T. To be submitted.
68. 33. a) Eisenstein, O.; Lefour, J. M.; Anh, N. T.; Hudson, R. F.; Tetrahedron, 1977, 33, 523.
69. b) Minot, C.; Anh, N. T. Tetrahedron, 1977, 33, 533.
70. 34. a) Dewar, M. J. S.; Pierini, A. B. J. Am. Chem. Soc., 1984, 106, 203.
71. b) Houk. K. N.; Li, Y.; Evanseck, J. D. Angew. Chem. Int. Ed. Engl., 1992, 31, 682.
72. c) Dewar, M. J. S.; Jie, C. Acc. Chem. Res., 1992, 25, 537.
73. d) Horn, B. A.; Herek, J. L.; Zewail, A. H. J. Am. Chem. Soc., 1996, 118, 8755.
74. 35. a) DELF 1990, ENRAF-NONIUS Molecular Structure Determination Package; MolEN Version 1990. Enraf-Nonius, Delft, The Netherlands.
75. b) International Tables for X-ray Crystallography 1974. Vol. IV. Birmingham : Kynoch Press. (Present distributeur D. Reidel, Dordrecht).
76. c) Johnson, C. K. 1965. ORTEP. Report ORNL-3794. Oak Ridge National Laboratory Tennessee, USA.
77. d) Walker, N. and Stuart, D. Acta Cryst., 1983, A39, 159.
78. 36. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; 3rd ed.; Butterworth-Heinemann Ltd.; Oxford, 1988.