A convenient synthesis of 2-amino-1,3-selenazoles using ionic liquids and microwave irradiation

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 186, Issue 8, 2011, Pages 1650-1654

  Maradolla, Mohanbabu ^a   Chandramouli, G V P ^a  

^a NATIONAL INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Bmim BF4; microwave irradiation; selenazoles; selenourea

Indexed keywords

EID: 80051747310     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426507.2010.527557     Document Type: Article

References (38)

1. (a) Back, T. G. (Ed.) Organoselenium Chemistry: A Practical Approach; Oxford University Press: Oxford, UK, 1999;
2. (b) Krief, A. In Comprehensive Organometallic Chemistry; W. W. Abel, F. G. A. Stone, G. Wilkinson, Eds.; Pergamon: Oxford, UK, 1995; vol. 11, p. 515;
3. (c) Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Oxford, UK, 1986;
4. (d) Block, E. Adv. Exp. Med. Biol. 1996, 401, 155-169;
5. (e) Bronzetti, G.; Della, C.; Aretini, P.; Fiorio, R. J. Environ. Pathol. Toxicol. Oncol. 1996, 15, 59-64;
6. (f) Schwartz, K.; Foltz, C. M. J. Am. Chem. Soc. 1957, 79, 3292-3293(f).
7. (a) Mills, G. C. J. Biol. Chem. 1957, 229, 189-197;
8. (b) Rotruck, J. T.; Pope, A. L.; Ganther, H. E.; Swanson, A. B.; Hafemann, D. G.; Hoekstra, W. G. Science 1973, 179, 588-590(b).
9. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667-3692.
10. Sheldon, R. Chem. Commun. 2001, 23, 2399-2407.
11. Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed. Engl. 2000, 39, 3772-3789.
12. Welton, T. Chem. Rev. 1999, 99, 2071-2084.
13. Brausch, N.; Metlen, A.; Wasserscheid, P. Chem. Commun. 2004, 13, 1552-1553.
14. Li, D.; Shi, F.; Peng, J.; Guo, S.; Deng, Y. J. Org. Chem. 2004, 69, 3582-3585.
15. Zhao, G.; Jiang, T.; Gao, H.; Han, B.; Haung, J.; Sun, D. Green. Chem. 2004, 6, 75-77.
16. Branco, L. C.; Afonso, C. A. M. J. Org. Chem. 2004, 69, 4381-4389.
17. Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114-8115.
18. Hagiwara, H.; Sugawara, Y.; Isobe, K.; Hoshi, T.; Suzuki, T. Org. Lett. 2004, 6, 2325-2328.
19. Earle, M. J.; Katdare, S. P.; Seddon, K. R. Org. Lett. 2004, 6, 707-710.
20. Valizadeh, H.; Amiri, M.; Gholipur, H. J. Heterocycl. Chem. 2009, 46, 108-110
21. Hofmann, G. Justus Liebigs Ann. Chem. 1889, 250, 294-322.
22. Koketsu, M.; Tanaka, H.; Ishihara, H. Chem. Lett. 2005, 34, 1260-1261.
23. Zhou, Y.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 2000, 83, 1576-1598.
24. Lai, L.-L.; Reid, D. H. Synthesis 1993, 870-872.
25. Geisler, K.; Pfeiffer, W.-D.; Künzler, A.; Below, H.; Bulka, E.; Langer, P. Synthesis 2004, 875-884.
26. Koketsu, M.; Mio, T.; Ishihara, H. Synthesis 2004, 233-236.
27. Geisler, K.; Pfeiffer, W.-D.; Muller, C.; Nobst, E.; Bulka, E.; Langer, P. Synthesis 2003, 1215-1220.
28. Maeda, H.; Kambe, N.; Sonoda, N.; Fujiwara, S.; Shinike, T. Tetrahedron 1997, 53, 13667-13680.
29. Zhang, P.-F.; Chen, Z.-C. J. Heterocycl. Chem. 2001, 38, 503-505.
30. Koketsu, M.; Imagawa, M.; Mio, T.; Ishihara, H. J. Heterocycl. Chem. 2005, 42, 831-834.
31. Geisler, K.; Künzler, A.; Below, H.; Bulka, E.; Pfeiffer, W.-D.; Langer, P. Synlett 2003, 1195-1197.
32. Dictionary of Organic Compounds, 6th ed.; Chapman and Hall: New York, 1995; Vol. 6, p. 5646.
33. Anastas, P. T.; Williamson, T. C.; Hjeresen, D. L.; Breen, J. Environ. Sci. Technol. 1993, 33, 116A-119A.
34. Pimentel, L. C. F.; de Souza, A. L. F.; Fernandez, T. L.; Wardell, J. L.; Antunes, O. A. C. Tetrahedron Lett. 2007, 48, 831-833.
35. (a) Narender, M.; Reddy, M. S.; Kumar, V. P.; Reddy, V. P.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2007, 72, 1849-1851;
36. (b) Potewar, T. M.; Ingale, S. A.; Srinivasan, K. V. Arkivoc 2008, (xii), 117-125(b).
37. (a) Narender, M.; Reddy, M. S.; Kumar, V. P.; Srinivas, B.; Sridhar, R.; Nageswar, Y. V. D.; Rao, K. R. Synthesis 2007, 3469-3472;
38. (b) Kanapickaite, V.; Martynaitis, V.; Sackus, A. Arkivoc 2009, (xi), 268-276(b).