Synthesis of condensed thiazoles. (Review)

Chemistry of Heterocyclic Compounds

Volumn 42, Issue 2, 2006, Pages 144-165

  Smirnova, N G ^a   Zavarzin, I V ^a   Krayushkin, M M ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Condensed thiazoles; Furothiazoles; Isoxazolothiazoles; Pyrazolothiazoles; Pyrrolothiazoles; Thiazoloisothiazoles; Thiazolopyridines; Thiazolothiazoles; Thienothiazoles

Indexed keywords

EID: 33646705417     PISSN: 00093122     EISSN: 15738353     Source Type: Journal    
DOI: 10.1007/s10593-006-0064-8     Document Type: Review

References (106)

1. D. Kikelj and U. Urleb, in: Science of Synthesis, Georg Thieme Verlag (2002), Vol. 11, p. 627.
2. Chem. Abstr., 139, 6779 (2003).
3. G. Pattenden, J. Heterocycl. Chem., 29, 607 (1992).
4. H. Ulrich, in: Science of Synthesis, Georg Thieme Verlag (2002), Vol. 11, p. 835.
5. Chem. Abstr., 139, 52895 (2003).
6. G. Seybold and H. Eilingsfeld, Liebigs Ann. Chem., 1271 (1979).
7. J. Barker, J. G. Kettle, and A. W. Faull, PCT Int. Appl. WO 9940914; Chem. Abstr., 131, 170342 (1999).
8. T. Ota, S. Komoritani, T. Yoshino, K. Uoto, Y. Nakamoto, H. Naito, A. Mochizuki, T. Nagata, H. Kanno, N. Haginoya, K. Yoshikawa, M. Nagamochi, and S. Kobayashi, Japan Kokai Tokkyo Koho JP 2003183286; Chem. Abstr., 139, 85363 (2003).
9. T. Ohta, S. Komoriya, T. Yoshino, K. Uoto, Y. Nakamoto, H. Naito, A. Mochizuki, T. Nagata, H. Kanno, N. Haginoya, K. Yoshikawa, M. Nagamochi, S. Kobayashi, and M. Ono, PCT Int. Appl. WO 0316302; Chem. Abstr., 138, 205076 (2003).
10. P. I. Abramenko, T. K. Ponomareva, and G. I. Priklonskikh, Khim. Geterotsikl. Soedin., 477 (1979).
11. P. I. Abramenko and V. G. Zhiryakov, Khim. Geterotsikl. Soedin., 1624 (1970).
12. V. R. Berdnikov, L. Ya. Kaplun, N. V. Pospelova, E. A. Silaev, and L. V. Formina, Russ. Patent RU 2195011; Chem. Abstr., 139, 141038 (2003).
13. E. B. Lifshits, A. V. Medvedeva, V. N. Podlesnykh, E. A Silaev, M. N. Ushomirskii, and L. V. Formina, Russ. Patent RU 2184387; Chem. Abstr., 138, 262613 (2003).
14. J. A. Zampese, F. R. Keene, and P. J. Steel, Dalton Transactions, 4124 (2004).
15. S. Ando, J. Nishida, Y. Inoue, S. Tokito, and Y. Yamashita, J. Mater. Chem., 14, 1787 (2004).
16. S. Ando, J. Nishida, E. Fujiwara, H. Tada, Y. Inoue, S. Tokito, and Y. Yamashita, Chem. Lett., 33, 1170 (2004).
17. V. Sutoris, Agrochemia (Bratislava), 30, No. 1, 15 (1990).
18. S. Reck, C. Nather, and W. Friedrichsen, Heterocycles, 48, 853 (1998).
19. L. Grehn, Chem. Scripta, 11, 199 (1977).
20. S. Hirabayashi and Y. Nagaoka, Japan Kokai Tokkyo Koho JP 03230158; Chem. Abstr., 116, 162453 (1992).
21. Y. Nagaoka and S. Hirabayashi, Eur. Pat. Appl. EP 407206; Chem. Abstr., 116, 31206 (1992).
22. Y. Oguchi and K. Arahara, Jpn. Patent JP 61228988; Chem. Abstr., 106, 224569 (1987).
23. H. Eilingsfeld and G. Swybold, Ger. Offen 2713573; Chem. Abstr., 90, 23035 (1978).
24. S. Athmani, M. F. Farhat, and B. Iddon, J. Chem. Soc., Perkin Trans. 1, 973 (1992).
25. E. Ceulemans, K. Vercauteren, L. K. Dyall, D. Buelens, and W. Dehaen, Tetrahedron, 9657 (1997).
26. G. L'Abbe, B. D'Hooge, and W. Dehaen, J. Chem. Soc. Perkin Trans. 1, 2379 (1995).
27. H. Eilingsfeld and R. Niess, Ger. Offen 2429195; Chem. Abstr., 84, 135649 (1976).
28. P. Bounaud and A. Vaino, PCT Int. Appl., WO 2005068473, http://www.espacenet.com.
29. M. S. Chande and P. V. R. Carvalho, Indian J. Chem., 43B, 378 (2004).
30. E. Ceulemans, L. K. Dyall, and W. Dehaen, Tetrahedron, 55, 1977 (1999).
31. P. I. Abramenko and V. G. Zhiryakov, Khim. Geterotsikl. Soedin., 1039 (1976).
32. V. K Gewald, M. Hentschel, and R. Heikel, J. Prakt. Chem., 315, 539 (1973).
33. V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Khim. Geterotsikl. Soedin., 1204 (1974).
34. N. I. Astrakhantseva, V. G. Zhiryakov, and P. I. Abramenko, Zh. Vses. Khim. Obshch., 21, 219 (1976).
35. P. Stanetty, T. Dvorak, and M. D. Mihovilovic, ARKIVOC, 1128 (2001)
36. C. Paulmier and F. Outurquin, J. Heterocycl. Chem., 20, 113 (1983).
37. S. Athmani and B. Iddon, Tetrahedron, 48, 7689 (1992).
38. I. Ya. Kvitko, R. V. Khozeeva, N. S. Fedorova, V. A. Smirnova, and A. V. El'tsov, Khim. Geterotsikl. Soedin., 474 (1979).
39. L. Grehn, J. Heterocycl. Chem., 15, 81 (1978).
40. Shafiee, A. Shafaati, and B. Habibi-Khameneh, J. Heterocycl. Chem., 26, 709 (1989).
41. Shafiee and A. Mazloumi, J. Heterocycl. Chem., 15, 1455 (1978).
42. N. I. Astrakhantseva, V. G. Zhiryakov, and P. I. Abramenko, Khim. Geterotsikl. Soedin., 1607 (1975).
43. N. I. Astrakhantseva, V. G. Zhiryakov, and P. I. Abramenko, Khim. Geterotsikl. Soedin., 1355 (1976).
44. L. D. Pinkin, V. G. Dzyubenko, P. I. Abramenko, and I. S. Shpileva, Khim. Geterotsikl. Soedin., 410 (1987).
45. P. I. Abramenko, T. K. Ponomareva, and G. P. Priklonskikh, Zh. Vses. Khim. Obshch., 23, 711 (1978).
46. M. I. A. Moneam and A. M. K. El-Dean, Phosphorus, Sulfur, Silicon Relat. Elem., 178, 2639 (2003).
47. V. G. Zhiryakov and I. I. Levkoev, Dokl. Akad. Nauk, 120, 1035 (1958);
48. Chem. Abstr., 52, 20128 (1958).
49. V. G. Zhiryakov, Khim. Nauka i Prom., 4, 680 (1959).
50. Hill, M. De Vleeschauwer, K. Houde, and M. Belley, Synlett, 407 (1998).
51. V. G. Zhiryakov, Khim. Nauk i Prom., 4, 573 (1959).
52. V. N. Yarovenko, F. M. Stoyanovich, O. Yu. Zolotarskaya, E. I. Chernoburova, I. V. Zavarzin, and M. M. Krayushkin, Izv. Akad. Nauk. Ser. Khim., 136 (2002).
53. V. Zavarzin, V. N. Yarovenko, A. Yu. Martynkin, and M. M. Krayushkin, in: The 18th International Symposium on the Organic Chemistry of Sulfur (13-18 July 1998), Abstracts, Florence, Italy, p. 106 (1998).
54. V. Zavarzin, V. N. Yarovenko, A. V. Shirokov, N. G. Smirnova, A. A. Es'kov, and M. M. Krayushkin, ARKIVOC, 205 (2003).
55. V. N. Yarovenko, S. A. Kosarev, I. V. Zarvarzin, and M. M. Krayushkin, Izv. Akad. Nauk. Ser. Khim., 753 (1999).
56. V. N. Yarovenko, S. A. Kosarev, I. V. Zarvarzin, and M. M. Krayushkin, Izv. Akad. Nauk. Ser. Khim., 1708 (2002).
57. V. N. Yarovenko, S. A. Kosarev, I. V. Zarvarzin, and M. M. Krayushkin, Izv. Akad. Nauk. Ser. Khim., 1387 (2002).
58. V. N. Yarovenko, S. A. Kosarev, A. V. Shirokov, I. V. Zavarzin, and M. M. Krayushkin, Izv. Akad. Nauk. Ser. Khim., 1487 (2000).
59. Ya. L. Gol'dfarb, Yu. B. Vol'kenshtein, and B. V. Lopatin Zh. Obshch. Khim., 34, 969 (1964).
60. V. N. Yarovenko, N. G. Smirnova, V. N. Bulgakova, I. V. Zavarzin, and M. M. Krayushkin, Zh. Org. Khim., 39, 1232 (2003).
61. I. V. Zavarzin, N. G. Smirnova, V. N. Yarovenko, and M. M. Krayushkin, Zh. Org. Khim., 40, 146 (2004).
62. Binder, G. Habison, and C. R. Noe, Synthesis, 255 (1977).
63. T. Nakamura, T. Hioki, K. Ohzeki, and N. Hanaki, US Patent Appl. Publ. US 2002 58216; Chem. Abstr., 136, 393179 (2002).
64. Shafiee, A. Mazloumi, and V.I. Cohen, J. Heterocycl. Chem., 16, 1563 (1979).
65. L. Grehn, Chem. Scripta, 13, 78 (1979).
66. El-Sharief, Phosphorus, Sulfur, Silicon Relat. Elem., 148, 117 (1999).
67. B. Eldon, J. Am. Chem. Soc., 118, 6141 (1996).
68. V. A. Ryabinin and A. N. Sinyakov, Biorganich. Khimiya, 24, 601 (1998).
69. N. G. Smirnova, I. V. Zavarzin, V. N. Yarovenko, and M. M. Krayushkin, in: I Youth Conference, Institute of Organic Chemistry, Russian Academy of Sciences. Abstracts [in Russian], Moscow (2005), p. 118.
70. G. A. El-Hiti, Monatsh. Chem., 134, 837 (2003).
71. Z. Zhang, T. S. Daynard, S. Wang, X. Du, G. B. Chopiuk, J. Yan, J. Chen, and S. V. Sviridov, PCT Int. Appl. WO 2004 11460; Chem. Abstr., 140, 163862 (2004).
72. Parlati, U. V. Ramesh, R. Singh, D. G. Payan, R. Lowe, and G. C. Look, Patent WO2005037845, http://www.espacenet.com.
73. M. Hemmerling and T. Klingstedt, Patent WO2004099204, http://www.espacenet.com.
74. Yasuda, K. Morimoto, S. Kanan, M. Hikota, T. Matsumoto, and K. Arakawa, Japan Kokai Tokkyo Koho 2004 2368; Chem. Abstr., 140, 71039 (2004).
75. M. D. Cowart, PCT Int. Appl. WO 03101994; Chem. Abstr., 140, 27845 (2004).
76. Brooks, D. T. Davies, G. E. Jones, R. E. Markwell, and N. D. Pearson, PCT Int. Appl. WO 03087098; Chem. Abstr., 139, 337959 (2003).
77. N. Haginoya, S. Kobayashi, S. Komoriya, T. Yoshino, M. Suzuki, T. Shimada, K. Watanabe, Y. Hirokawa, T. Furugori, and T. Nagahara, J. Med. Chem., 47, 5167 (2004)
78. N. Haginoya, S. Kobayashi, S. Komoriya, T. Yoshino, T. Nagata, Y. Hirokawa, and T. Nagahara, Bioorg. Med. Chem., 12, 5579 (2004).
79. N. Haginoya, S. Kobayashi, S. Komoriya, Y. Hirokawa, T. Furugori, and T. Nagahara, Bioorg. Med. Chem. Lett., 14, 2935 (2004).
80. Hayakawa and Y. Tanaka, Heterocycles, 22, 1697 (1984).
81. Schäfer, H. Hartmann, and K. Gewald, J. Prakt. Chem., 316, 19 (1974).
82. I. D. Komaritsa, Khim. Geterotsikl. Soedin., 1547 (1989).
83. D. C. Leysen, A. Haemers, and W. Bollaert, J. Heterocycl. Chem., 21, 401 (1984).
84. Shafiee and H. Ghazar, J. Heterocycl. Chem., 23, 1171 (1986).
85. El-Desoky and Aboul-Fetouh, J. Chem. Technol. Biotechnol., 67, 153 (1996).
86. T. Y. Shen, R. L. Clark, A. A. Pessolano, B. E. Witzel, and T. J. E. Yanza, Ger. Patent DE 2330109 (1974); Chem. Abstr., 80, 95916 (1974).
87. N. Suzuki and R. Dohmori, Chem. Pharm. Bull., 27, 410 (1979).
88. Couture, P. Grandclaudon, and E. Huguerre, J. Heterocycl. Chem., 24, 1765 (1987).
89. Couture, E. Huguerre, and P. Grandclaudon, Synth. Commun., 19, 713 (1989).
90. Zhu, M. Zhang, and M. Dai, J. Heterocycl. Chem., 42, 727 (2005).
91. D. G. Kulkarni, S. R. Lokhande, and B. G. Khadse, Indian J. Pharm. Sci., 43, No. 2, 37 (1981);
92. Chem. Abstr., 95, 169055 (1981).
93. W. Altlang and G. A. Molander, J. Heterocycl. Chem., 14, 129 (1977).
94. W. Altlang, J. Org. Chem., 41, 3395 (1976).
95. R. D. Norcross, US Patent US2005065151, http://www.espacenet.com.
96. Tsuruoka and Y. Kaku, Chem. Pharm. Bull., 46, 623 (1998).
97. Smith, C. M. Lindsay, and J. K. Morris, Chem. Ind. (London), 302 (1988).
98. Eunsook Ma, Molecules, 8, 678 (2003).
99. Smith, D. Anderson, and I. Matthews, Sulfur Lett., 18, 79 (1995).
100. N. Haginoya, S. Komoriya, K. Osanai, T. Yoshino, T. Nagata, M. Nagamochi, R. Muto, M. Yamaguchi, T. Nagahara, and H. Kanno, Heterocycles, 63, 1555 (2004)
101. T. Takahashi and H. Saikashi, J. Pharm. Soc. Japan, 64, 201 (1944).
102. S. G. Fridman, Zh. Obshch. Khim., 26, 613 (1956).
103. S. G. Fridman, Zh. Obshch. Khim., 26, 864 (1956).
104. Kramberger and P. Lorencak, J. Heterocycl. Chem., 12, 337 (1975).
105. I. V. Zavarzin, N. G. Smirnova, V. N. Yarovenko, and M. M. Krayushkin, Izv. Akad. Nauk. Ser. Khim., 1299 (2004).
106. I. V. Zavarzin, N. G. Smirnova, V. N. Yarovenko, and M. M. Krayushkin, Zh. Org. Khim., 42, 288 (2006).