Efficient synthesis of 2-unsubstituted 1,3-selenazoles

Synlett

Volumn , Issue 8, 2003, Pages 1195-1197

  Geisler, Karlheinz ^a   Künzler, Andreas ^a   Below, Harald ^a   Bulka, Ehrenfried ^a   Pfeiffer, Wolf Diethard ^a   Langer, Peter ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

1,3 selenazoles; Cyclization; Fragmentation; Oxidation; Selenium heterocycles

Indexed keywords

1,3 SELENAZOLE DERIVATIVE; 2 BENZOYL 1,3 SELENAZOLE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; INFRARED SPECTROSCOPY; SYNTHESIS;

EID: 0038053148     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39884     Document Type: Article

References (31)

1. For the antibiotically active C-glycosyl selenazole selenazofurin, see: (a) Goldstein, B. M.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc. 1990, 112, 8265; and references cited therein. (b) Shafiee, A.; Khashayarmanesh, Z.; Kamal, F. J. Sci., Islamic Repub. Iran 1990, 1, 11. (c) Shafiee, A.; Shafaati, A.; Khamench, B. H. J. Heterocycl. Chem. 1989, 26, 709. (d) For cancerostatic activity of 1,3-selenazoles see: Srivastava, P. C.; Robins, R. K. J. Med. Chem. 1983, 26, 445. (e) Shafiee, A.; Mazloumi, A.; Cohen, V. J. J. Heterocycl. Chem. 1979, 16, 1563.
2. For the antibiotically active C-glycosyl selenazole selenazofurin, see: (a) Goldstein, B. M.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc. 1990, 112, 8265; and references cited therein. (b) Shafiee, A.; Khashayarmanesh, Z.; Kamal, F. J. Sci., Islamic Repub. Iran 1990, 1, 11. (c) Shafiee, A.; Shafaati, A.; Khamench, B. H. J. Heterocycl. Chem. 1989, 26, 709. (d) For cancerostatic activity of 1,3-selenazoles see: Srivastava, P. C.; Robins, R. K. J. Med. Chem. 1983, 26, 445. (e) Shafiee, A.; Mazloumi, A.; Cohen, V. J. J. Heterocycl. Chem. 1979, 16, 1563.
3. For the antibiotically active C-glycosyl selenazole selenazofurin, see: (a) Goldstein, B. M.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc. 1990, 112, 8265; and references cited therein. (b) Shafiee, A.; Khashayarmanesh, Z.; Kamal, F. J. Sci., Islamic Repub. Iran 1990, 1, 11. (c) Shafiee, A.; Shafaati, A.; Khamench, B. H. J. Heterocycl. Chem. 1989, 26, 709. (d) For cancerostatic activity of 1,3-selenazoles see: Srivastava, P. C.; Robins, R. K. J. Med. Chem. 1983, 26, 445. (e) Shafiee, A.; Mazloumi, A.; Cohen, V. J. J. Heterocycl. Chem. 1979, 16, 1563.
4. For the antibiotically active C-glycosyl selenazole selenazofurin, see: (a) Goldstein, B. M.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc. 1990, 112, 8265; and references cited therein. (b) Shafiee, A.; Khashayarmanesh, Z.; Kamal, F. J. Sci., Islamic Repub. Iran 1990, 1, 11. (c) Shafiee, A.; Shafaati, A.; Khamench, B. H. J. Heterocycl. Chem. 1989, 26, 709. (d) For cancerostatic activity of 1,3-selenazoles see: Srivastava, P. C.; Robins, R. K. J. Med. Chem. 1983, 26, 445. (e) Shafiee, A.; Mazloumi, A.; Cohen, V. J. J. Heterocycl. Chem. 1979, 16, 1563.
5. For the antibiotically active C-glycosyl selenazole selenazofurin, see: (a) Goldstein, B. M.; Kennedy, S. D.; Hennen, W. J. J. Am. Chem. Soc. 1990, 112, 8265; and references cited therein. (b) Shafiee, A.; Khashayarmanesh, Z.; Kamal, F. J. Sci., Islamic Repub. Iran 1990, 1, 11. (c) Shafiee, A.; Shafaati, A.; Khamench, B. H. J. Heterocycl. Chem. 1989, 26, 709. (d) For cancerostatic activity of 1,3-selenazoles see: Srivastava, P. C.; Robins, R. K. J. Med. Chem. 1983, 26, 445. (e) Shafiee, A.; Mazloumi, A.; Cohen, V. J. J. Heterocycl. Chem. 1979, 16, 1563.
6. (a) Larsen, R. 1,3-Selenazoles, In Comprehensive Heterocyclic Chemistry II, Shinkai I., Katritzky A., Rees C. W., Scriven E. F. V., Vol. 3; Elsevier Science: Oxford, 1996, Chap. 8.
7. (b) Wirth, T. Organoselenium Chemistry, in Modern Developments in Organic Synthesis; Springer: Berlin, 2000.
8. (a) Koketsu, M.; Nada, F.; Ishihara, H. Synthesis 2002, 195.
9. (b) Geisler, K.; Jacobs, A.; Künzler, A.; Mattes, M.; Girrleit, I.; Zimmermann, B.; Bulka, E.; Pfeiffer, W.-D.; Langer, P. Synlett 2002, 1983.
10. (c) Kaminski, R.; Glass, R. S.; Skowronska, A. Synthesis 2001, 1308.
11. (d) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408.
12. (e) Koketsu, M.; Fukuta, Y.; Ishihara, H. Tetrahedron Lett. 2001, 42, 6333.
13. (f) Zhang, P.-F.; Chen, Z.-C. Synthesis 2000, 1219.
14. (g) Maeda, H.; Kambe, N.; Sonoda, N.; Fujiwara, S.-i.; Sini-ike, T. Tetrahedron 1997, 53, 13667.
15. (h) Lai, L.-L.; Reid, D. H. Synthesis 1993, 870.
16. (i) Ogawa, A.; Miyaka, J.; Karasaki, Y.; Murai, S.; Sonoda, N. J. Org. Chem. 1985, 50, 384.
17. (j) Cohen, V. J. Synthesis 1978, 668.
18. Haginiwa, J. Yakugaku Zasshi 1948, 68, 191.
19. Maeda, H.; Kambe, N.; Sonoda, N.; Fujiwara, S.-i.; Sini-ike, T. Tetrahedron 1997, 53, 13667; and references cited therein.
20. For 2-benzoyl-1,3-benzoselenazole, see: Mbuyi, M.; Evers, M.; Tihange, G.; Luxen, A.; Christiaens, L. Tetrahedron Lett. 1983, 5873.
21. 13NSe (298.25): C, 64.44; H, 4.39; N, 4.70. Found: C, 6.40; H, 4.20; N, 4.79. All products gave correct spectroscopic data and correct elemental analyses and/or high resolution mass data.
22. 11NOSe (312.22): C, 61.55; H, 3.55; N, 4.49. Found: C, 61.80; H, 3.90; N, 4.29.
23. 11NSe (284.22): C, 63.39; H, 3.90; N, 4.93. Found: C, 63.21; H, 3.94; N, 4.93.
24. 2-Unsubstituted 1,3-thiazoles have been prepared by decarboxylation of 1,3-thiazolyl-2-carboxylic acids; see for example: (a) Sarodnick, G.; Kempter, G. Pharmazie 1983, 38, 829. (b) Pirotte, B.; Delarge, J. J. Chem. Res., Miniprint 1990, 7, 1634. (c) Strehlke, P. Chem. Ber. 1973, 106, 721. (d) Sarodnick, G.; Kempter, G. Z. Chem. 1979, 19, 21.
25. 2-Unsubstituted 1,3-thiazoles have been prepared by decarboxylation of 1,3-thiazolyl-2-carboxylic acids; see for example: (a) Sarodnick, G.; Kempter, G. Pharmazie 1983, 38, 829. (b) Pirotte, B.; Delarge, J. J. Chem. Res., Miniprint 1990, 7, 1634. (c) Strehlke, P. Chem. Ber. 1973, 106, 721. (d) Sarodnick, G.; Kempter, G. Z. Chem. 1979, 19, 21.
26. 2-Unsubstituted 1,3-thiazoles have been prepared by decarboxylation of 1,3-thiazolyl-2-carboxylic acids; see for example: (a) Sarodnick, G.; Kempter, G. Pharmazie 1983, 38, 829. (b) Pirotte, B.; Delarge, J. J. Chem. Res., Miniprint 1990, 7, 1634. (c) Strehlke, P. Chem. Ber. 1973, 106, 721. (d) Sarodnick, G.; Kempter, G. Z. Chem. 1979, 19, 21.
27. 2-Unsubstituted 1,3-thiazoles have been prepared by decarboxylation of 1,3-thiazolyl-2-carboxylic acids; see for example: (a) Sarodnick, G.; Kempter, G. Pharmazie 1983, 38, 829. (b) Pirotte, B.; Delarge, J. J. Chem. Res., Miniprint 1990, 7, 1634. (c) Strehlke, P. Chem. Ber. 1973, 106, 721. (d) Sarodnick, G.; Kempter, G. Z. Chem. 1979, 19, 21.
28. (a) Geisler, K.; Below, H.; Möller, A.; Bulka, E. Z. Chem. 1984, 24, 99.
29. (b) For the synthesis of an 1,3-oxaseleno derivative, see: Weber, M.; Hartmann, H. Z. Chem. 1987, 27, 95.
30. 3NSe: C, 11.11; H, 2.80; N, 13.02. Found: C, 11.40; H, 3.10; N, 13.11. The solidification of 6 can be achieved only for crude products of good purity. Decomposition of selenoformamide (6) occurred upon standing at 20°C. However, it can be stored at -20°C for several days. Freshly prepared material should be used for reactions.
31. Cyclization of 6 with 1d. To an EtOH solution of 6 (1.1 g, 10 mmol) was added 1d (2.4 g, 10 mmol) and pyridine (0.79 g, 10 mmol). The solution was gently warmed, the precipitate formed was filtered off and the filtrate was concentrated. The product precipitated upon standing of the solution at 0°C and was recrystallized from dry i-PrOH or EtOH to give 5d as slight yellow needles (2.00 g, 79%), mp 160-162°C.