Synthesis of 2,2-dimethyl-2H-chromenes

Heterocycles

Volumn 53, Issue 5, 2000, Pages 1193-1203

  Lévai, Albert ^a   Tímár, Tibor ^b   Sebök, Péter ^b   Eszenyi, Tibor ^b  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b ICN Hungary Co Ltd   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMENE DERIVATIVE;

ALKYLATION; ARTICLE; CYCLIZATION; DESICCATION; HEATING; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0343183172     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-99-528     Document Type: Article

References (97)

1. R.L. Shriner and A.G. Sharp, J. Org. Chem., 1939, 4, 575.
2. L.I. Smith and P.M. Rouoff, J. Am. Chem. Soc., 1940, 62, 145.
3. W.S. Bowers, T. Ohta, J.S. Cleere, and P.A. Marsella, Science, 1976, 193, 542.
4. T.R. Kasturi and T. Manithomas, Tetrahedron Lett., 1967, 2573.
5. W.S. Bowers, 'The Juvenile Hormones', ed. by L.I. Gilbert, Plenum Press, Nowe York, 1976, p. 394.
6. J. Mann and P.D. Kane, Tetrahedron Lett., 1985, 26, 4677.
7. T. Ohta, R.J. Kuhr, and W.S. Bowers, J. Agric. Food Chem., 1977, 25, 478.
8. M.V. Naidu and G.S. Krishna Rao, Indian J. Chem., 1979, 17B, 73.
9. M.L. Wolfrom, E.W. Koos, and H.B. Bhat, J. Org. Chem., 1967, 32, 1058.
10. J.R. Beck, R. Kwok, R.N. Booher, A.C. Brown, L.E. Patterson, P. Pranc, B. Rockey, and A. Pohland, J. Am. Chem. Soc., 1968, 90, 4706.
11. T. Ohta and W.S. Bowers, Chem. Pharm. Bull, 1977, 25, 2788.
12. W. Biernacki and W. Sobotka, Polish. J. Chem., 1979, 53, 2275.
13. W. Biernacki and W. Sobotka, Polish. J. Chem., 1980, 54, 2239.
14. F. Camps, J. Coll., A. Messeguer, and M.A. Pericás, Tetrahedron Lett., 1980, 21, 2361.
15. M. Tsukuyama, T. Sakomoto, T. Horie, M. Masumura, and M. Nakayama, Heterocycles, 1981, 16, 955.
16. A. Banerji and N.C. Goomer, Indian J. Chem., 1981, 20B, 144.
17. (a) P. Anastasis and P.E. Brown, J. Chem. Soc., Perkin Trans. 1, 1982, 2013;
18. (b) F. Camps, A. Conchillo, and A. Messeguer, Z. Naturforsch., 1985, 40b, 556.
19. J.W. ApSimon, L.W. Herman, and C. Huber, Can. J. Chem., 1985, 63, 2589.
20. P. Teixidor, F. Camps, and A. Messeguer, Heterocycles, 1988, 27, 2459.
21. P. Sebo″k, T. Tímár, J.Cs. Jászberényi, and Gy. Batta, Heterocycles, 1988, 27, 2595.
22. T. Tímár and J.Cs. Jászberényi, J. Heterocycl. Chem., 1988, 25, 871.
23. (a) T. Tímár, S. Hosztafi, J.Cs. Jászberényi, K.E. Kövér, and Gy. Batta, Acta Chim. Hung., 1988, 125, 303;
24. (b) T. Tímár, J.Cs. Jászberényi, and S. Hosztafi, Acta Chim. Hung., 1988, 125 457;
25. (c) T. Tímár, S. Hosztafi, and J.Cs. Jászberényi, Acta Chim. Hung., 1988, 125, 617;
26. (d) T. Tímár, J.Cs. Jászberényi, and S. Hosztafi, Acta Chim. Hung., 1989, 126, 149;
27. (e) P. Sebo″k, T. Tímár, J.Cs. Jászberényi, and J. Jeko″, Acta Chim. Hung., 1989, 126, 471;
28. (f) T. Tímár, J.Cs. Jászberényi, and S. Hosztafi, Acta Chim. Hung., 1989, 126, 487.
29. A. Lévai, G. Tóth, Á. Szöllo″sy, and T. Tímár, Monatsh. Chem., 1990, 121, 403.
30. A. Lévai and T. Tímár, Pharmazie, 1990, 45, 660 and 728.
31. T. Tímár, P. Sebo″k, T. Eszenyi, and J.Cs. Jászberényi, Heterocycles, 1994, 38, 2719.
32. T. Tímár, T. Eszenyi, P. Sebo″k, and J. Jeko″, Heterocycl. Commun., 1995, 1, 253.
33. A. Lévai and T. Tímár, Heterocycles, 1989, 29, 2335.
34. A. Lévai and T. Tímár, Synth. Commun., 1990, 20, 641.
35. (a.) V.K. Ahluwalia, R.S. Jolly, and A.K. Tehim, Tetrahedron, 1982, 38, 3673;
36. (b) V.K. Ahluwalia, R.S. Jolly, and. S. Bala, Chem. Ind.(London), 1982, 369;
37. (c) V.K. Ahluwalia, M. Khanna, and R.P. Singh, Synthesis, 1983, 404;
38. (d) V.K. Ahluwalia and A.K. Tehim, Monatsh. Chem., 1983, 114, 1381;
39. (e) F. Camps, J. Coll, A. Messeguer, M. A. Pericás, and S. Ricart, Synthesis, 1979, 126;
40. (f) F. Camps, O. Colonina, J, Coll, and A. Messeguer, Tetrahedron, 1982, 38, 2955.
41. (a) A. Lévai and T. Tímár, Synthesis, 1990, 339;
42. (b) A. Lévai, Monatsh. Chem., 1992, 123, 461.
43. G. Solladié, D. Boeffel, and J. Maignan, Tetrahedron, 1996, 52, 2065.
44. J. Hlubucek, E. Ritchie, and W.C. Taylor, Tetrahedron Lett., 1969, 1369.
45. R. Hug, Gy. Fráter, H.-J. Hansen, and H. Schmid, Helv. Chim. Acta, 1971, 54, 306.
46. J. Hlubucek, E. Ritchie, and W.C. Taylor, Aust. J. Chem., 1971, 24, 2347.
47. W.K. Andersen, E.J.LaNoie, and P.G. Whitkop, J. Org. Chem., 1974, 39, 881.
48. A.K. Mathur, Indian J. Chem., 1977, 15B, 1065.
49. R. Chénevert, J.M. Perron, R. Paquin, M. Robitaille, and Y.K. Wang, Experientia, 1980, 36, 379.
50. V.K. Ahluwalia, C. Prakash, and R. Gupta, Tetrahedron, 1982, 38, 609.
51. B.K. Rohatgi and R.N. Khanna, Indian J. Chem., 1983, 22B, 1150.
52. J.M. Evans, C.S. Fake, T.C. Hamilton, R.H. Poyser, and E.A. Watts, J. Med. Chem., 1983, 26, 1582.
53. D.R. Buckle, R.S. Arch, A.E. Fenwick, C.S.V. Houge-Frydrych, J.L. Pinto, D.G. Smith, S.G. Taylor, and J.M. Tedder, J. Med. Chem., 1990, 33, 3028.
54. P.E. Brown, R.A. Lewis, and M.A. Waring, J. Chem. Soc., Perkin Trans. 1, 1990, 2979.
55. M. Yogo, C. Ito, and H. Furukawa, Chem. Pharm. Bull., 1991, 39, 328.
56. P.E. Brown and R.A. Lewis, J. Chem. Soc., Perkin Trans. 1, 1992, 573.
57. J.D. Godfrey, Jr., R.H. Mueller, T.C. Sedergran, N. Sundararajan, and V.J. Colandrea, Tetrahedron Lett., 1994, 35, 6405.
58. R. Cruz-Almanza, F. Pérez-Flores, L. Brena, E. Tapia, R. Ojeda, and A. Fuentes, J. Heterocycl. Chem., 1995, 32, 219.
59. J.T. North, D.R. Kronenthal, A.J. Pullokaran, S.R. Real, and H.Y. Chen., J. Org. Chem., 1995, 60, 3397.
60. D. Bell, M.R. Davies, G.R. Geen, and I.S. Mann, Synthesis, 1995, 707.
61. H.J. Knölker and C. Hofmann, Tetrahederon Lett., 1996, 37, 7947.
62. C.Z. Ding, Synth. Commun., 1996, 26, 4267.
63. F. Bigi, S. Carloni, R. Maggi, C. Muchetti, and G. Sartori, J. Org. Chem., 1997, 62, 7024.
64. G. Cardillo, R. Criccio, and L. Merlini, Tetrahedron, 1968, 24, 4825.
65. A.C. Jain and M.K. Zutshi, Tetrahedron Lett., 1971, 3179.
66. G. Cardillo, M. Orena, G. Porzi, and S. Sandri, J. Chem. Soc., Chem. Commun., 1979, 836.
67. A. Bongini, G. Cardillo, M. Orena, G. Porzi, and S. Sandri, Tetrahedron Lett., 1979, 2545.
68. M. Uchiyama and J.C. Overeem, Recl. Trav. Chim. Pays-Bas, 1981, 100, 408.
69. P. Baran, N.C. Baran, and R.P. Sharma, Tetrahedron Lett., 1983, 24, 5801.
70. M.J. Cortés, G.R. Haddad, and J.A. Valderrama, Heterocycles, 1984, 22, 1951.
71. G. Pandey and A. Krishna, J. Org. Chem., 1988, 53, 2364.
72. M. Iyer and G. K. Trivedi, Synth. Commun., 1990, 20, 1347.
73. R.C. Larock, L. Wei, and T.R. Hightower, Synlett, 1998, 522.
74. G. Sartori, G. Casiraghi, L. Bolzoni, and G. Casnati, J. Org. Chem., 1979, 44, 803.
75. F. Camps, J. Coll, A. Messeguer, and M.A. Pericás, J. Heterocycl. Chem., 1980, 17, 1377.
76. E. Kiehlmann, J.E. Conn, and J.H. Borden, Org. Prep. Proced. Int., 1982, 14, 337.
77. J.J. Talley, Synthesis, 1983, 845.
78. S. Bissada, C.K. Lan, M.A. Bernstein, and C. Dufresne, Can. J. Chem., 1994, 72, 1866.
79. R. Cruz-Almanza, F. Pérez-Flores, J. Cárdenas, C. Vázquez, and A. Fuentes, Synth Commun., 1994, 24, 1009.
80. R. Cruz-Almanza, F. Pérez-Flores, and C. Lemini, Heterocycles, 1994, 37, 759.
81. B.A. Chandler, C.C. Lopes, R.S.C. Lopes, A.J.M. daSilva, and V. Snieckus, Synthesis, 1998, 279.
82. W.M. Bandarayane, L. Crombie, and D.A. Whiting, J. Chem. Soc., Chem. Commun., 1969, 970.
83. O.P. Malik, R.S. Kapil, and N. Anand, Indian J. Chem., 1976, 14B, 449.
84. P. Thomas and D.A. Whiting, Tetrahedron Lett., 1984, 25, 1099.
85. B. Begasse and M. Le Corre, Tetrahedron, 1980, 36, 3409.
86. G. Ariamala and K.K. Balasubramanian, Tetrahedron Lett., 1988, 29, 3487.
87. G. Ariamala and K.K. Balasubramanian, J. Chem. Soc., Chem. Commun., 1988, 34.
88. G. Ariamala and K.K. Balasubramanian, Tetrahedron, 1989, 45, 309.
89. P.E. Brown, W.Y. Marcus, and P. Anastasis, J. Chem. Soc., Perkin Trans. 1, 1985, 1127.
90. T. Eszenyi and T. Tímár, Synth Commun., 1990, 20, 3219.
91. R. Bergman and R. Gericke, J. Med. Chem., 1990, 33, 492.
92. T. Eszenyi, T. Tímár, and P. Sebo″k, Tetrahedron Lett., 1991, 32, 827.
93. C.D. Gabbutt, D.J. Hartley, J.D. Hepworth, B.M. Heron, M. Kanjia, and M.M. Rahman, Tetrahedron, 1994, 50, 2507.
94. C.D. Gabbutt, J.D. Hepworth, and B. M. Heron, Tetrahedron, 1995, 51, 13277.
95. T. Eszenyi, Zs. Zsótér, P. Sebo″k, and T. Tímár, Heterocycl. Commun., 1998, 4, 155.
96. K. Tsushima, M. Hatakoshi, N. Matsuo, N. Ohno, and I. Nakayama, Agric. Biol. Chem., 1985, 49, 2421.
97. J. Tércio, B. Ferreira, V. Catani, and J.V. Comasseto, Synthesis, 1987, 149.