Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles

Tetrahedron Letters

Volumn 49, Issue 47, 2008, Pages 6709-6711

  Piatnitski Chekler, Eugene L ^a   Elokdah, Hassan M ^a   Butera, John ^a  

^a PFIZER INC   (United States)

Author keywords

Kinase inhibitor; One pot cyclization; Oxadiazole

Indexed keywords

ALIPHATIC CARBOXYLIC ACID; AROMATIC CARBOXYLIC ACID; CARBOXYLIC ACID; OXADIAZOLE DERIVATIVE; THIOSEMICARBAZIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; FILTRATION; ONE POT SYNTHESIS; PRECIPITATION; REACTION ANALYSIS;

EID: 53149120307     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.057     Document Type: Article

References (32)

1. Blouin, M.; Grimm, E. L.; Gareau, Y.; Gagnon, M.; Juteau, H.; Laliberte, S.; Mackay, B.; Friesen, R. WO 2006099735, 2006.
2. Barth, F.; Congy, C.; Gueule, P.; Rinaldi-Carmona, M.; Van Broeck, D. WO 2006087480, 2006.
3. Birch, A. M.; Bowker, S. S.; Butlin, R. J.; Donald, C. S.; McCoull, W.; Nowak, T.; Plowright, A. WO 2006064189, 2006.
4. Leber, J. D.; Li, M.; Lee, J.; Aubart, K. M.; Christensen, S. B. WO 2005032550, 2005.
5. Handlon, A. L.; Akwabi-Ameyaw, A.; Brown, K.; De Anda, F.; Drewry, D.; Fang, J.; Irsula, O.; Li, G.; Linn, J. A.; Milliken, N. O.; Ramanjulu, J. Abstracts of Papers, 226th ACS National Meeting, 2003.
6. Madhavan R., and Srinivasan V.R. Indian J. Chem. 7 (1969) 760-765
7. Biwersi, C. M.; Warmus, J. S.; Zhang, L. Y.; Barrett, S. D.; Kaufman, M. D.; Plummer, M. S.; Reed, J. E. WO 2004056789, 2004.
8. Kiselyov A.S., Semenova M., Semenov V.V., Piatnitski E., and Ouyang S. Bioorg. Med. Chem. Lett. 16 (2006) 2559
9. Piatnitski, E. L.; Kiselyov, A. S.; Doody, J.; Hadari, Y. R.; Ouyang, S.; Chen, X. WO 2004052280, 2004.
10. Black, S. L.; Kaufman, M. D.; Ortwine, D. F.; Plummer, M. S.; Quin, J.; Rewcastle, G. W.; Shahripour, A. B.; Spicer, J. A.; Whitehead, C. E. WO 2005000818, 2005.
11. Ouyang X., Piatnitski E.L., Pattaropong V., Chen X., He H.-Y., Kiselyov A.S., Velankar A., Kawakami J., Labelle M., Smith L., Lohman J., Lee S.P., Malikzay A., Fleming J., Gerlak J., Wang Y., Rosler R.L., Zhou K., Mitelman S., Camara M., Surguladze D., Doody J.F., and Tuma M.C. Bioorg. Med. Chem. Lett. 16 (2006) 1191-1196
12. Hiremath S.P., Biradar J.S., and Kudari S.M. J. Indian Chem. Soc. 61 (1984) 74-76
13. Dumciute J., Martynaitis V., Holzer W., Mangelinckx S., De Kimpe N., and Sackus A. Tetrahedron 62 (2006) 3309
14. Amir M., and Kumar S. Pharmazie 60 (2005) 175
15. Dolman S.J., Gosselin F., O'Shea P.D., and Davies I.W. J. Org. Chem. 25 (2006) 9548-9551
16. Hassan A.A., El-Shaieb K.M., Shaker R.M., and Doepp D. Heteroat. Chem. 16 (2005) 12
17. Madhavan R., and Srinivasan V.R. Indian J. Chem. 7 (1969) 760-765
18. Omar F.A., Mahfouz N.M., and Rahman M.A. Eur. J. Med. Chem. 31 (1996) 819-825
19. Marcewicz-Rojewska B., and Bilinski S. Acta Pol. Pharm. 37 (1980) 159-167
20. Gumien D. Biuletyn Informacyjny Instytutu Lekow 30 (1983) 179-186
21. Sawhney S.N., Singh J., and Bansal O.P. Indian J. Chem. 13 (1975) 804-807
22. Hiremath S.P., Bajji A.C., and Biradar J.S. Proc. Natl. Acad. Sci., India Sec. A: Phys. Sci. 62 (1992) 161-166
23. Kelarev V.I., Shvekhgeimer G.A., and Lunin A.F. Khim. Geterotsikl. (1984) 1271-1276
24. Dehuri S.N., Pradhan P.C., and Nayak A. Indian J. Chem. Sect. B: Org. Chem. Including Med. Chem. 22B (1983) 815-816
25. Dehuri S.N., Pradhan P.C., and Nayak A. J. Indian Chem. Soc. 60 (1983) 475-478
26. Coppo F.T., Evans K.A., Graybill T.L., and Burton George. Tetrahedron Lett. 45 (2004) 3257-3260
27. Bilinski S., Bielak L., Chmielewski J., Marcewicz-Rojewska B., and Musik I. Acta Pol. Pharm. 46 (1989) 343-349
28. Gierczyk B., Nowak-Wydra B., Grajewski J., and Zalas M. Magn. Reson. Chem. 45 (2007) 123-127
29. Simiti I., and Ghiran D. Farmacia (Bucharest, Romania) 19 (1971) 199-205
30. Baxendale I.R., Ley S.V., and Martinelli M. Tetrahedron 61 (2005) 5323-5349
31. Gehlen H., and Drohla R. J. Prakt. Chem. (Leipzig) 311 (1969) 539-548
32. Brain C.T., and Brunton S.A. Synlett (2001) 382-384