Facile Syntheses of Oxazolines and Thiazolines with N-Acylbenzotriazoles under Microwave Irradiation

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 811-814

  Katritzky, Alan R ^a   Cai, Chunming ^a   Suzuki, Kazuyuki ^a   Singh, Sandeep K ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IRRADIATION; MICROWAVES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

MICROWAVE REACTIONS;

ORGANIC COMPOUNDS;

2 (4 CHLOROPHENYL) 4,4 DIMETHYL 4,5 DIHYDRO 1,3 OXAZOLE; 2 (4 CHLOROPHENYL) 4,5 DIHYDRO 1,3 THIAZOLE; 2 (4 CHLOROPHENYL) 5,6 DIHYDRO 4H 1,3 OXAZINE; 2 (4 METHOXYPHENYL) 4,5 DIHYDRO 1,3 THIAZOLE; 2 (4 METHYLPHENYL) 4,5 DIHYDRO 1,3 THIAZOLE; 2 (4 NITROPHENYL) 4,5 DIHYDRO 1,3 THIAZOLE; 2 (4 NITROPHENYL) 5,6 DIHYDRO 4H 1,3 OXAZINE; 2 AMINO 2 METHYLPROPANOL; 2,2' (1,4 PHENYLENE)BIS(4,5 DIHYDRO 1,3 THIAZOLE); 2,2' (1,4 PHENYLENE)BIS(4,5 DIHYDRO 4,4 DIMETHYL 1,3 OXAZOLE); 4 BENZYL 2 PHENYL 4,5 DIHYDRO 1,3 OXAZOLE; 4,4 DIMETHYL 2 (4 METHOXYPHENYL) 4,5 DIHYDRO 1,3 OXAZOLE; 4,4 DIMETHYL 2 (4 METHYLPHENYL) 4,5 DIHYDRO 1,3 OXAZOLE; 4,4 DIMETHYL 2 (4 NITROPHENYL) 4,5 DIHYDRO 1,3 OXAZOLE; 5,6 DIHYDRO 4H 1,3 OXAZINE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; BISOXAZOLINE; BISTHIAZOLINE; MERCAPTAMINE; N ACYLBENZOTRIAZOLE DERIVATIVE; OXAZOLINE DERIVATIVE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; MICROWAVE IRRADIATION; SYNTHESIS;

MICROWAVES; OXAZOLES; THIAZOLES; TRIAZOLES;

EID: 0842328944     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0355092     Document Type: Article

References (81)

1. Frump, J. A. Chem. Rev. 1971, 71, 483.
2. Fustero, S.; Salavert, E.; Navarro, A.; Mojarrad, F.; Fuentes, A. S. Targets Heterocycl. Syst. 2001, 5, 235; Chem. Abstr. 2001, 138, 221480.
3. Fustero, S.; Salavert, E.; Navarro, A.; Mojarrad, F.; Fuentes, A. S. Targets Heterocycl. Syst. 2001, 5, 235; Chem. Abstr. 2001, 138, 221480.
4. (a) Peterson, T.; Falk, K.-E.; Leong, S. A.; Klein, M. P.; Neilands, J. B. J. Am. Chem. Soc. 1980, 102, 7715.
5. (b) Genet, J.-P.; Thorimbert, S.; Touzin, A.-M. Tetrahedron Lett. 1993, 34, 1159.
6. (c) Hamada, Y.; Kato, S.; Shioiri, T. Tetrahedron Lett. 1985, 26, 3223.
7. (d) Wipf, P.; Miller, C. P. J. Am. Chem. Soc. 1992, 114, 10975.
8. (e) Li, Q.; Woods, K. W.; Claiborne, A.; Gwaltney, S. L., II; Barr, K. J.; Liu, G.; Gehrke, L.; Credo, R. B.; Hui, Y. H.; Lee, J.; Warner, R. B.; Kovar, P.; Nukkala, M. A.; Zielinski, N. A.; Tahir, S. K.; Fitzgerald, M.; Kim, K. H.; Marsh, K.; Frost, D.; Ng, S.-C.; Rosenberg, S.; Sham, H. L. Bioorg. Med. Chem. Lett. 2002, 12, 465.
9. (f) Campiani, G.; de Angelis, M.; Armaroli, S.; Fattorusso, C.; Catalanotti, B.; Ramunno, A.; Nacci, V.; Novellino, E.; Grewer, C.; Ionescu, D. ; Rauen, T.; Griffiths, R.; Sinclair, C.; Fumagalli, E.; Mennini, T. J. Med. Chem. 2001, 44, 2507.
10. (a) Meyers, A. I.; Mihelich, E. D. Angew. Chem., Int. Ed. Engl. 1976, 270.
11. (b) Reuman, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
12. (c) Meyers, A. I.; Temple, D. L.; Haidukewych, D.; Mihelich, E. D. J. Org. Chem. 1974, 39, 2787.
13. (d) Meyers, A. I. Acc. Chem. Res. 1978, 11, 375.
14. (e) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
15. (a) Boyce, R. J.; Mulqueen, G. C.; Pattenden, G. Tetrahedron Lett. 1994, 35, 5705.
16. (b) White, J. D.; Kim, T.-S.; Nambu, M. J. Am. Chem. Soc. 1995, 117, 5612.
17. (c) Toya, Y.; Takagi, M.; Kondo, T.; Nakata, H.; Isobe, M.; Goto, T. Bull. Chem. Soc. Jpn. 1992, 65, 2604.
18. (d) Einsiedel, J.; Hübner, H.; Gmeiner, P. Bioorg. Med. Chem. Lett. 2001, 11, 2533.
19. (e) Zarantonello, P.; Leslie, C. P.; Ferritto, R.; Kazmierski, W. M. Bioorg. Med. Chem. Lett. 2002, 12, 561.
20. (f) Wipf, P.; Reeves, J. T.; Balachandran, R.; Day, B. W. J. Med. Chem. 2002, 45, 1901.
21. (a) Wenker, H. J. Am. Chem. Soc. 1935, 57, 9.
22. (b) Vorbrüggen, H.; Krolikiewicz, K. Tetrahedron Lett. 1981, 22, 4471.
23. (c) Vorbrüggen, H.; Krolikiewicz, K. Tetrahedron Lett. 1993, 49, 9353.
24. (d) Cwik, A.; Hell, Z.; Hegedüs, A.; Finta, Z.; Horváth, Z. Tetrahedron Lett. 2002, 43, 3985.
25. (e) Marrero-Terrero, A. L.; Loupy, A. Synlett 1996, 245.
26. (f) Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2003, 44, 2331.
27. (g) Meyers, A. I.; Slade, J. J. Org. Chem. 1980, 45, 2785.
28. (h) Kamata, K.; Agata, I.; Meyers, A. I. J. Org. Chem. 1998, 63, 3113.
29. (i) Oussaid, B.; Berlan, J.; Soufiaoui, M.; Garrigues, B. Synth. Commun. 1995, 25, 659.
30. (j) Badiang, J. G.; Aube, J. J. Org. Chem. 1996, 61, 2484.
31. (k) Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.
32. (l) Clarke, D. S.; Wood, R. Synth. Commun. 1996, 26, 1335.
33. (m) Jnaneshwara, G. K.; Deshpande, V. H.; Lalithambika, M.; Ravindranathan, T.; Bedekar, A. V. Tetrahedron Lett. 1998, 39, 459.
34. (a) Busacca, C. A.; Dong, Y.; Spinelli, E. M. Tetrahedron Lett. 1996, 37, 2935.
35. (b) Boden, C. D. J.; Pattenden, G.; Ye, T. Synlett 1995, 417.
36. (c) Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908.
37. (d) Nishio, T. Tetrahedron Lett. 1995, 36, 6113.
38. (e) Wipf, P.; Fritch, P. C. Tetrahedron Lett. 1994, 35, 5397.
39. (f) Lafargue, P.; Guenot, P.; Lellouche, J.-P. Synlett 1995, 171.
40. (g) Mahler, S. G.; Serra, G. L.; Antonow, D.; Manta, E. Tetrahedron Lett. 2001, 42, 8143.
41. (h) Wipf, P.; Miller, C. P.; Venkatraman, S.; Fritch, P. C. Tetrahedron Lett. 1995, 36, 6395.
42. Lion, C.; Dubois, J. E. Tetrahedron 1973, 29, 3417.
43. (a) Katritzky, A. R.; Shobana, N.; Pernak, J.; Afridi, A. S.; Fan, W.-Q. Tetrahedron 1992, 48, 7817.
44. (b) Katritzky, A. R.; He, H.-Y.; Suzuki, K. J. Org. Chem. 2000, 65, 8210.
45. (c) Katritzky, A. R.; Chang, H.-X.; Yang, B. Synthesis 1995, 503.
46. (d) Katritzky, A. R.; Yang, B.; Semenzin, D. J. Org. Chem. 1997, 62, 726.
47. (e) Katritzky, A. R.; Pastor, A.; Voronkov, M. V. J. Heterocycl. Chem. 1999, 36, 777.
48. (f) Katritzky, A. R.; Pastor, A. J. Org. Chem. 2000, 65, 3679.
49. (g) Katritzky, A. R.; Suzuki, K.; Singh, S. K.; He, H.-Y. J. Org. Chem. 2003, 68, 5720.
50. (h) Katritzky, A. R.; Suzuki, K.; Singh, S. K. Croat. Chim. Acta 2003, in press.
51. (i) Katritzky, A. R.; Huang, T.-B.; Voronkov, M. V. J. Org. Chem. 2000, 65, 8069.
52. (a) Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light; CEM Publishing: Matthews, NC, 2002.
53. (b) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
54. (c) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
55. (d) Caddick, S. Tetrahedron 1995, 51, 10403.
56. (e) Fini, A.; Breccia, A. Pure Appl. Chem. 1999, 71, 573.
57. (f) Katritzky, A. R.; Singh, S. K. Arkivoc 2003, 13, 68.
58. (a) Varma, R. S. Green Chem. 1999, 1, 43.
59. (b) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
60. Katritzky, A. R.; Zhang, Y.; Singh, S. K. Synthesis 2003, in press.
61. Meyers, A. I.; Gabel, R.; Mihelich, E. D. J. Org. Chem. 1978, 43, 1372.
62. Wang, L.; Chen, Z.-C. Synth. Commun. 2001, 31, 1633.
63. Kreutzberger, V. A.; Dietz, E. Arzneim.-Forsch. 1970, 20, 1723.
64. Katritzky, A. R.; Wang, M.; Zhang, S. Arkivoc 2001, 9, 19.
65. Luo, W.; Tang, G. Zhongguo Shengwu Yixue Gongcheng Xuebao 2001, 20, 335; Chem. Abstr. 2001, 137, 68000.
66. Luo, W.; Tang, G. Zhongguo Shengwu Yixue Gongcheng Xuebao 2001, 20, 335; Chem. Abstr. 2001, 137, 68000.
67. Lu, C. X.; Li, Q.; Pan, J. J. Polym. Sci., Polym. Chem. 1985, 23, 3031.
68. Pridgen, L. N.; Killmer, L. B. J. Org. Chem. 1981, 46, 5402.
69. Mohan, R.; Katzenellenbogen, J. A. J. Org. Chem. 1984, 49, 1238.
70. Boyd, R. N.; Rittner, R. C. J. Am. Chem. Soc. 1960, 82, 2032.
71. Feuer, H.; Bevinakatti, H. S.; Luo, X.-G. J. Heterocycl. Chem. 1986, 23, 825.
72. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891.
73. Kakehi, A.; Ito, S.; Uchiyama, K.; Konno, Y.; Kondo, K. J. Org. Chem. 1977, 42, 443.
74. Schmir, G. L. J. Am. Chem. Soc. 1965, 87, 2743.
75. Iwakura, Y.; Nabeya, A.; Nishiguchi, T. J. Org. Chem. 1967, 32, 2362.
76. Hagen, H.; Becke, F. German Patent 2202369, 1973; Chem. Abstr. 1973, 79, 105241.
77. Bose, A. K.; Manhas, M. S.; Chib, J. S.; Chawla, H. P. S.; Dayal, B. J. Org. Chem. 1974, 39, 2877.
78. Wipf, P.; Wang, X. J. Comb. Chem. 2002, 4, 656.
79. Aitken, R. A.; Armstrong, D. P.; Galt, R. H. B.; Mesher, S. T. E. J. Chem. Soc., Perkin Trans. 1 1997, 935.
80. Zioudrou, C.; Schmir, G. L. J. Am. Chem. Soc. 1963, 85, 3258.
81. Katritzky, A. R.; Langthorne, R. T.; Patel, R. C.; Lhommet, G. Tetrahedron 1981, 37, 2383.