Multicomponent synthesis of dihydropyrimidines and thiazines

Chemistry - A European Journal

Volumn 12, Issue 27, 2006, Pages 7178-7189

  Vugts, Danielle J ^a   Koningstein, Manoe M ^a   Schmitz, Rob F ^a   De Kanter, Frans J J ^a   Groen, Marinus B ^a   Orru, Romano V A ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

Heterocycles; HeteroDiels Alder reaction; HornerWadsworth Emmons reaction; Microwave assisted synthesis; Multicomponent reactions

Indexed keywords

ALDEHYDES; CYANIDES; MICROWAVES; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

HETEROCYCLES; HETERODIELS-ALDER REACTION; HORNERWADSWORTH-EMMONS REACTION; ISOCYANATES; MICROWAVE-ASSISTED SYNTHESIS; NITRILES; PHOSPHONATES;

NITROGEN COMPOUNDS;

EID: 33749031569     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600168     Document Type: Article

References (70)

1. L. F. Tietze. Chem. Rev. 1996, 96, 115-136.
2. a) A. Domling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344:
3. Angew. Chem. Int. Ed. 2000, 39. 3169-3210:
4. b) A. Domling, Chem. Rev. 2006, 106, 17-89.
5. L. Banfi, R. Riva, in Organic Reactions, Vol. 65 (Ed.: L.E. Overman). Wiley, Hoboken, New Jersey (USA), 2005. pp. 1-140.
6. a) J. P. Zhu, Eur. J. Org. Chem. 2003, 7, 1133-1144:
7. b) H. Bienayme, C. Hulme. G. Oddon, P. Schmitt. Chem. Eur. J. 2000, 6, 3321-3329.
8. R. V. A. Orru, M. de Greef, Synthesis 2003, 1471-1499.
9. a) A recent issue of Chem. Rev. 2004, 104, 2125-2812, Guest editor A. Katritzky, was completely devoted to heterocycles:
10. b) C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 24, 4957-4980.
11. a) R. S. Bon, C. G. Hong, M. J. Bouma. R. F. Schmitz, F. J. J. de Kanter. M. Lutz. A. L. Spek. R. V. A. Orru, Org. Lett. 2003, 5, 3759-3762:
12. b)R. S. Bon, B. van Vliet, N.E. Sprenkels, R. F. Schmitz, F. J. J. de Kanter. C. V. Stevens, M. Swart, F. M. Bickelhaupt, R. V. A. Orru, J. Org. Chem. 2005, 70, 3542-3553;
13. E. Gelens, F. J. J. de Kanter, R. F. Schmitz, L. A. J. M. Sliedregt, B. J. van Steen, C. G. Kruse, R. Leurs, M. B. Groen, R. V. A. Orru. Mol. Diversity 2006, 10, 17-22.
14. a) D. J. Vugts, H. Jansen, R. F. Schmitz, F. J. J. de Kanter, R. V. A. Orru, Chem. Commun. 2003, 2594-2595.
15. b) For related work on the preparation of azadienes, see also refs. [19a] and [19b].
16. a) C. O. Kappe. Acc. Chem. Res. 2000, 33, 879-888, and references therein;
17. b) C. O. Kappe, QSAR Comb. Sci. 2003, 22, 630-645.
18. G. C. Rovnyak, S. D. Kimball, B. Beyer, G. Cucinotta, J. D. Dimarco, J. Gougoutas, A. Hedberg, M. Malley, J. P. McCarthy, R. A. Zhang, S. Moreland, J. Med. Chem. 1995, 38, 119-129.
19. K. S. Atwal, B. N. Swanson, S. E. Unger, D. M. Floyd, S. Moreland, A. Hedberg. B. C. Oreilly, J. Med. Chem. 1991, 34, 806-811.
20. a) K. S. Atwal. B. C. Oreilly, J. Z. Gougoutas. M. F. Malley, Heterocycles 1987, 26, 1189-1192;
21. b) B. C. Oreilly, K. S. Atwal, Heterocycles 1987, 26, 1185-1188;
22. K. S. Atwal, G. C. Rovnyak, B. C. Oreilly, J. Schwartz, J. Org. Chem. 1989, 54, 5898-5907.
23. E. Gossnitzer, G. Feierl, U. Wagner, Eur. J. Pharm. Sci. 2002, 15, 49-61.
24. B. B. Snider, Z. P. Shi. J. Org. Chem. 1993, 58, 3828-3839.
25. A. D. Shutalev, E. A. Kishko, N. V. Sivova, A. Y. Kuznetsov, Molecules 1998, 3, 100-106.
26. a)M. C. Elliott, M.S. Long, Org. Biomol. Chem. 2004, 2, 2003-2011;
27. b) M. C. Elliott, M. S. Long, Tetrahedron Lett. 2002, 43, 9191-9194;
28. M. C. Elliott, E. Kruiswijk, D. J. Willock, Tetrahedron 2001, 57, 10139-10146;
29. M. C. Elliott, E. Kruiswijk, M.S. Long, Tetrahedron 2001, 57, 6651-6677.
30. C. O. Kappe. Eur. J. Med. Chem. 2000, 35, 1043-1052.
31. a) R. Perez, T. Beryozkina, O. I. Zbruyev, W. Haas, C. O. Kappe, J. Comb. Chem. 2002, 4, 501-510;
32. b) A. S. Paraskar, G. K. Dewkar, A. Sudalai, Tetrahedron Lett. 2003, 44, 3305-3308;
33. S. Martinez, M. Meseguer, L. Casas, E. Rodriguez, E. Molins, M. Moreno-Manas, A. Roig, R. M. Sebastian, A. Vallribera, Tetrahedron 2003, 59, 1553-1556.
34. a) K. Lee, D. Y. Oh, Synthesis 1991, 213-214;
35. b) W. S. Shin, K. Lee. D. Y. Oh, Tetrahedron Lett. 1995, 36, 281;
36. G. Sumrell, J. Org. Chem. 1954, 19, 817-819.
37. A. K. Bhattacharya, O. Thyagarajan, Chem. Rev. 1981, 81, 415-430.
38. For examples, sec: a)J. J. Kiddle. Synth. Commun. 2001, 31, 3377-3382;
39. b) B. Boutevin, Y. Hervaud, T. Jeanmaire, A. Boulahna, M. Elasri, Phosphorus Sulfur Silicon Relat. Elem. 2001, 174, 1-14:
40. R. O. Gillis, J. F. Horwood, G. L. White, J. Am. Chem. Soc. 1958, 80, 2999-3002;
41. F. Kagan, R. D. Birkenmeyer, R.E. Strube, J. Am. Chem. Soc. 1959, 81, 3026-3031;
42. J.J. Kiddle, A. F. Gurley, Phosphorus Sulfur Silicon Relat. Elem. 2000, 160, 195-205;
43. f) D. Villemin, F. Simeon, H. Decreus, P. A. Jaffres, Phosphorus Sulfur Silicon Relat. Elem. 1998, 133, 209-213;
44. g) J. Y. Winum, M. Kamal, H. Agnaniet, A. Leydet, J. L. Montero, Phosphorus Sulfur Silicon Relat. Elem. 1997, 129, 83-88.
45. Phosphoramidate a, bearing an additional Me group, was also identified. Equation Presented
46. Besides the phosphoramidates, considerable amounts of the phosphonate b were also observed. Equation Presented
47. B. E. Maryanoff, A. B. Reitz. Chem. Rev. 1989, 89, 863-927.
48. a) M. P. Teulade. P. Savignac, E. E. Aboujaoude, N. Collignon, J. Or-ganomet, Chem. 1986. 312, 283-295;
49. b) M. N. Mattson, H. Rapoport, J. Org, Chem. 1996, 61, 6071-6074.
50. W. B. Jang, K. Lee, C. W. Lee, D. Y. Oh, Chem. Commun. 1998, 609-610.
51. D. Strubing, H. Neumann, S. Hubner, S. Klaus, M. Beller, Org. Lett. 2005, 7, 4321-4324.
52. a) L. F. Tietze, J. Fennen, H. Geissler, G. Schulz, E. Anders, Liebigs Ann. 1995, 1681-1687;
53. b) M. Behforouz, M. Ahmadian, Tetrahedron 2000, 56, 5259-5288;
54. M. C. Elliott, E. Kruiswijk, J. Chem. Soc. Perkin Trans. 1 1999, 3157-3166.
55. A. Dondoni, A. Massi, S. Sabbatini, V. Bertolasi, J. Org. Chem. 2002, 67, 6979-6994.
56. Y. Huang, F. Yang, C. Zhu, J. Am. Chem. Soc. 2005, 127, 16386-16387.
57. a) M. S. Newman, W. C. Liang, J. Org. Chem. 1973, 38, 2438-2441;
58. b) L.J. Zhang, Y. Z. Huang, J. Organomet, Chem. 1993, 454, 101-103;
59. T. R. Barbee, K.F. Albizati, J. Org. Chem. 1991, 56, 6764-6773;
60. I. Shimizu, T. Sugiura, J. Tsuji, J. Org. Chem. 1985, 50, 537-539.
61. a) G. A. Strohmeier, W. Haas, C. O. Kappe, Chem. Eur. J. 2004, 10, 2919-2926;
62. b) G. A. Strohmeier, C. O. Kappe, Angew. Chem. 2004. 116, 631-634;
63. Angew. Chem. Int. Ed. 2004, 43, 621-624.
64. For reviews on the Dimroth rearrangement, sec: a) E. S. H. El
65. Ashry, Y. El Kilany, N. Rashed, H. Assafir, Adv. Heterocycl. Chem. 1999, 75, 79-167;
66. b) M. Wahren, Z. Chem. 1969, 9, 241-252;
67. D. J. Brown in Mechanisms of Molecular Migrations, Vol. 1 (Ed. : B. S. Thyagarajan), Wiley-Interscience, New York, 1968. 1. 209-245.
68. a) D. J. Brown, J. S. Harper. J. Chem. Soc. 1963, 1276-1284;
69. b) D. J. Brown, B. T. England, J. Chem. Soc. C 1971, 14, 2507-2512.
70. T. N. Glasnov, D. J. Vugts, M. M. Koningstein, B. Desai, W. M. F. Fabian, R. V. A. Orru, C. O. Kappe, QSAR Comb. Chem. 2006, in press.