Experimental and theoretical FMO interaction studies of the Diels-Alder reaction of 5-acetyl-3-methythio-1,2,4-triazine with cyclic enamines

Tetrahedron

Volumn 61, Issue 34, 2005, Pages 8148-8158

  Lipińska, Teodozja ^a  

^a SIEDLCE UNIVERSITY OF NATURAL SCIENCES AND HUMANITIES   (Poland)

Author keywords

1,2,4 Triazines; 3 (Acetyl) cycloalka c pyridines; Aza Diels Alder reaction; Frontier molecular orbitals interactions; Secondary FMOs interplay in transition state

Indexed keywords

5 ACETYL 3 METHYLTHIO 1,2,4 TRIAZINE; ALKALOID DERIVATIVE; ENAMINE; PYRIDINE DERIVATIVE; SEMPERVIRINE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; ENERGY; MOLECULAR INTERACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

BETULACEAE;

EID: 22544434632     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.06.043     Document Type: Article

References (67)

1. Part 32 in a series '1,2,4-Triazines in Organic Synthesis'. For Part 31, see: Branowska, D.; Rykowski, A. Tetrahedron Lett., in print.
2. For rewiews, see: (a) D.L. Boger, and S.N. Weinreb H.H. Wasserman Hetero Diels-Alder Methodology in Organic Synthesis Vol. 47 1987 Academic New York Chapters 9 and 10
3. T. Kametani, and S. Hibino A.R. Katritzky Advances in Heterocyclic Chemistry Vol. 42 1987 Academic New York 245 333
4. D.L. Boger Bull. Chim. Soc. Belg. 99 1990 599 615
5. H. Neunhoeffer A.R. Katritzky C.W. Rees E.F.V. Scriven Comprehensive Heterocyclic Chemistry II Vol. 6 1996 Pergamon Oxford 507 574
6. D.L. Boger J. Heterocycl. Chem. 35 1998 1001 1011
7. For preliminary studies, see: (a) W. Dittmar, J. Sauer, and A. Steigel Tetrahedron Lett. 1969 5171 5174
8. A. Steigel, and J. Sauer Tetrahedron Lett. 1970 3357 3360
9. H. Neunhoeffer, and H.-W. Frühauf Liebigs Ann. Chem. 758 1972 121 131
10. For example, see: (a) H. Reim, A. Steigel, and J. Sauer Tetrahedron Lett. 1975 2901 2904
11. J. Balear, G. Chrisam, F.X. Huber, and J. Sauer Tetrahedron Lett. 24 1983 1481 1484
12. K. Mueller, and J. Sauer Tetrahedron Lett. 25 1984 2541 2544
13. M.G. Barlow, R.N. Haszeldine, and D. Simpkin J. Chem. Soc., Perkin Trans. 1 1982 1245 1249
14. S.C. Benson, J.L. Gross, and J.K. Snyder J. Org. Chem. 55 1990 3257 3269
15. J. Sauer Bull. Soc. Chim. Belg. 101 1992 521 540
16. E.C. Taylor, and J.E. Macor Tetrahedron Lett. 26 1985 2415 2418
17. G. Seitz, L. George, and S. Dietrich Tetrahedron Lett. 26 1985 4355 4358
18. E.C. Taylor, and J.L. Pont J. Org. Chem. 52 1987 4287 4292
19. E.C. Taylor, and J.E. Macor J. Org. Chem. 52 1987 4287 4292
20. V.N. Charushin, B. van Veldhuizen, H.C. van der Plas, and C.H. Stam Tetrahedron 45 1989 6499 6512
21. E.C. Taylor, J.E. Macor, and L.G. French J. Org. Chem. 56 1991 1807 1812
22. S.C. Benson, J. Li, and J.K. Snyder J. Org. Chem. 57 1992 5285 5287
23. J. Li, and J.K. Snyder J. Org. Chem. 58 1993 516 519
24. B. Rickborn L.A. Paguette The Retro Diels-Alder Reaction. Part II. Dienephiles with One or More Heteroatom Organic Reactions Vol. 53 1998 Wiley Chapters I.D. and IV.D. with Table and References cited therein
25. D.L. Boger, and J.S. Panek J. Org. Chem. 46 1981 2179 2182
26. D.L. Boger, J.M. Panek, and M.M. Meier J. Org. Chem. 47 1982 895 897
27. D.L. Boger, M. Patel, and M.D. Mulican Tetrahedron Lett. 1982 4559 4563
28. H. Neunhoeffer, and H.-J. Metz Justus Liebiegs Ann. Chem. 1983 1476 1496
29. E.C. Taylor, K.F. McDaniel, and J.C. Warner Tetrahedron Lett. 28 1987 1977 1980
30. E.C. Taylor, and J.C. Warner Heterocycles 26 1987 2673 2685
31. B.L. Chenard, and R.T. Ronau J. Org. Chem. 53 1988 5175 5177
32. E.C. Taylor, and J.E. Macor J. Org. Chem. 54 1989 1249 1256
33. M. Ohba, R. Izuta, and E. Shimizu Tetrahedron Lett. 41 2000 10251 10255
34. P. Hautefaye, B. Cimetière, A. Pierré, S. Léonce, J. Hickman, W. Laine, C. Bailly, and G. Lavielle Bioorg. Med. Chem. Lett. 13 2003 2731 2725
35. H. Neunhoeffer, and B. Lehman Justus Liebigs Ann. Chem. 1977 1413 1420
36. Z.-K. Wan, and J.K. Snyder Tetrahedron Lett. 39 1998 2487 2490
37. J. Sauer, D.K. Heldman, and G.R. Pabst Eur. J. Org. Chem. 1999 313 321
38. T. Lipińska, D. Branowska, and A. Rykowski Khim. Geterosikl. Soedin. 1999 381 389
39. S.P. Stanforth, B. Tarbit, and M.D. Watson Tetrahedron Lett. 43 2002 6015 6017
40. D. Branowska Synthesis 2003 2089 2094
41. V.N. Kozhevnikov, D.N. Kozhevnikov, T.V. Nikitina, V.L. Rusinov, O.N. Chupakhin, M. Zabel, and B. König J. Org. Chem. 68 2003 2882 2888
42. B.R. Lahue, Z.-K. Wan, and J.K Snyder J. Org. Chem. 68 2003 4345 4354
43. D. Branowska Tetrahedron 60 2004 6021 6027
44. S.A. Raw, and R.J.K. Taylor Tetrahedron Lett. 45 2004 8607 8610
45. S.A. Raw, and R.J.K. Taylor J. Am. Chem. Soc. 126 2004 12260 12261
46. A. Rykowski, and T. Lipińska Pol. J. Chem. 71 1997 83 90
47. A. Rykowski, and A. Lipińska Synth. Commun. 26 1996 4409 4414
48. T. Lipińska Tetrahedron Lett. 43 2002 9565 9657
49. T. Lipińska Tertahedron Lett. 45 2004 8331 8334
50. M.A. McCarric, Y.D. Wu, and K.N. Houk J. Am. Chem. Soc. 114 1992 1499 1500
51. J. Cislowski, J. Sauer, J. Hetzenegger, T. Karcher, and T. Hierstetter J. Am. Chem. Soc. 115 1993 1353 1359
52. I. Fleming Frontiers Orbitals and Organic Chemical Reactions 1976 Wiley London
53. A. Rauk Orbital Interaction Theory in Organic Chemistry 1994 Wiley New York
54. I. Fleming Pericyclic Reactions 1999 Oxford University Press Oxford, New York, Tokyo
55. For role of secondary orbitals interaction, see: (a) D. Ginsburg Tetrahedron 39 1983 2095 2135
56. B.S. Juric J. Chem. Soc., Perkin Trans. 2 1999 373 378
57. J.I. Garcia, J.A. Mayoral, and L. Salvatella Acc. Chem. Res. 33 2000 658 664
58. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart J. Am. Chem. Soc. 107 1985 3902 3909
59. J.J.P. Stewart J. Comput. Aided Mol. Des. 4 1990 1 105
60. (c) Stewart, J. J. P. Fujitsu Limited, Tokyo; FQS Poland, MOPAC 2002 in CACHe 5.0 software.
61. A. Rykowski, E. Olender, D. Branowska, and H.C. van der Plas Org. Prep. Proced. Int. 33 2001 501 503
62. H. Neunhoeffer, H.-W. Henning, M. Frühauf, and M. Mutterer Tetrahedron Lett. 1969 3147 3150
63. W.W. Paudler, and T.K. Chen J. Heterocycl. Chem. 7 1970 767 770
64. D.D. Perrin, and W.L.F. Armarego Purification of Laboratory Chemicals 1992 Pergamon Oxford
65. M.E. Kuehne J. Am. Chem. Soc. 81 1959 5400 5404
66. G.M. Sheldrick Acta Crystallogr., Sect. A 46 1990 467 473
67. Sheldrick, G. M. SHELXL 97: Program for Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1993.