An efficient potassium cyanide-promoted synthesis of 2-arylbenzoxazoles from [4.3.0]boron heterobicycles

Tetrahedron Letters

Volumn 51, Issue 19, 2010, Pages 2633-2635

  López Ruiz, Heraclio ^a   Briseño Ortega, Horacio ^a   Rojas Lima, Susana ^a   Santillán, Rosa ^b   Farfán, Norberto ^c  

^a UNIVERSIDAD AUTÓNOMA DEL ESTADO DE HIDALGO   (Mexico)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

^c Universidad Nacional Autonoma de Mexico Facultad de Quimica   (Mexico)

Author keywords

2 Arylbenzoxazoles; Boronates; NMR; Potassium cyanide; Schiff bases

Indexed keywords

2 ARYLBENZOXAZOLE DERIVATIVE; BORON; METHANOL; NITRILE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM CYANIDE; TETRACYCLIC NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS; X RAY ANALYSIS;

EID: 77950459706     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.027     Document Type: Article

References (52)

1. Deluca M.R., and Kervin S.M. Tetrahedron Lett. 38 (1997) 199-202
2. Sato Y., Yamada M., Yoshida S., Soneda T., Ishikawa M., Nizato T., Suzuli K., and Konno F. J. Med. Chem. 41 (1998) 3015-3021
3. Temiz O., Oren I., Sener E., Yalcin I., and Ucarturk N. Farmaco 53 (1998) 337-341
4. Wang C., Widon J., Petronijevic F., Burnett J.C., Nuss J.E., Bavari S., Gussio R., and Wipf P. Heterocycles 79 (2009) 487-520
5. Rodriguez A.D., Ramirez C., Rodriguez I.I., and Gonzalez E. Org. Lett. 1 (1999) 527-530
6. Davidson J.P., and Corey E.J. J. Am. Chem. Soc. 125 (2003) 13486-13489
7. Ueki M., Ueno K., Miyadoh S., Abe K., Shibata K., Taniguchi M., and Oi S. J. Antibiot. 46 (1993) 1089-1094
8. Sato S., Kajiura T., Noguchi M., Takehana K., Kobavashi T., and Tsuji T. J. Antibiot. 54 (2001) 102-104
9. Don M.-J., Shen C.-C., Lin Y.-L., Syu Jr. W., Ding Y.-H., and Sun C.-M. J. Nat. Prod. 68 (2005) 1066-1070
10. Tully D.C., Liu H., Alper P.B., Chatterjee A.K., Epple R., Roberts M.J., Williams J.A., Nguyen K.T., Woodmansee D.H., Tumanut C., Li J., Spraggon G., Chang J., Tuntland T., Harris J.L., and Karanewsky D.S. Bioorg. Med. Chem. Lett. 16 (2006) 1975-1980
11. Grobler J.A., Dornadula G., Rice R.M., Simcoe A.L., Hazuda D.J., and Miller M.D. J. Biol. Chem. 282 (2007) 8005-8010
12. Leventhal L., Brandt M.R., Cummonts T.A., Piesla M.J., Rogers K.E., and Harris H.A. Eur. J. Pharmacol. 553 (2006) 146-148
13. Nishiu J., Ito M., Ishida Y., Kakutani M., Shibata T., Matsushita M., and Shindo M. Diabetes Obes. Metab. 8 (2006) 508-516
14. Easmon J., Pürstinger G., Thies K.-S., Heinisch G., and Hofmann J. J. Med. Chem. 49 (2006) 6343-6350
15. Rasmussen K., Hsu M.-A., and Yang Y. Neuropsychopharmacology 32 (2007) 786-792
16. Leaver I.H., and Milligam B. Dyes Pigm. 5 (1984) 109-144
17. For a general overview of synthesis methods to benzoxazoles, see: (a) Boyd, G.V. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Schaumann, E., Ed.; Stuttgart: Thieme, 2002; Vol. 11, pp 481-492
18. Lin A., and Yang L. Tetrahedron Lett. 46 (2005) 4315-4319
19. Kawashita Y., Nakamichi N., Kawabata H., and Hayashi M. Org. Lett. 5 (2003) 3713-3715
20. Kidwai M., Bansal V., Saxena A., Aerry S., and Mozudar S. Tetrahedron Lett. 47 (2006) 8049-8053
21. Kumar D., Rudrawar S., and Chakaborti A.K. Aust. J. Chem. 61 (2008) 881-887
22. Johnson S.M., Connelly S., Wilson I.A., and Kelly J.W. J. Med. Chem. 51 (2008) 260-270
23. Orlando C.M., Wirth J.G., and Heath D.R. J. Org. Chem. 9 (1970) 3147-3149
24. Evindar G., and Batey R.A. J. Org. Chem. 71 (2006) 1802-1808
25. Viirre R.D., Evindar G., and Batey R.A. J. Org. Chem. 73 (2008) 3452-3459
26. Bonnamour J., and Bolm C. Org. Lett. 10 (2008) 2665-2667
27. Saha P., Ramana T., Purkait N., Ali M.A., Paul R., and Punniyamurthy T. J. Org. Chem. 74 (2009) 8719-8725
28. Kantam M.L., Venkanna G.T., Kumar K.B.S., Balasubrahmanyam V., and Bhargava S. Synlett 11 (2009) 1753-1756
29. Chang J., Zhao K., and Pan S. Tetrahedron Lett. 43 (2002) 951-954
30. Warma R.S., Saini R.K., and Prakash O. Tetrahedron Lett. 38 (1997) 2621-2622
31. Nakagawa K., Onoue H., and Sugita J. Chem. Pharm. Bull. 12 (1961) 1135-1138
32. Srivastava R.G., and Venkataramani R.S. Synth. Commun. 18 (1988) 1537-1544
33. Praveen C., Kumar K.H., Muralidharan D., and Perumal P.T. Tetrahedron 64 (2008) 2369-2374
34. Varma R.S., and Kumar D. J. Heterocycl. Chem. 35 (1998) 1539-1540
35. Nakawawa K., Onoue H., and Sugita J. Chem. Pharm. Bull. 12 (1964) 1135-1138
36. Stephens F.F., and Bower J.D. J. Chem. Soc. (1949) 2971-2972
37. Park K.H., Jun K., Shin S.R., and Oh S.W. Tetrahedron Lett. 37 (1996) 8869-8870
38. Chen W.-H., and Pang Y. Tetrahedron Lett. 50 (2009) 6680-6683
39. Shoar R.H., Heidary M., Farzaneh M., and Malakouti R. Synth. Commun. 39 (2009) 1742-1751
40. Chen Y.-X., Qian L.F., Zhang W., and Han B. Angew. Chem., Int. Ed. 47 (2008) 9330-9333
41. Baltork I.M., Moghadam M., Tangestaninejad S., Mirkhani V., Zolfigol M.A., and Hojati S.F. J. Iran. Chem. Soc. 5 (2008) S65-S70
42. Ponnala S., and Sahu D.P. Synth. Commun. 36 (2006) 2189-2194
43. Kawashita Y., Nakamishi N., Kawabata H., and Hayashi M. Org. Lett. 5 (2003) 3713-3715
44. Barba V., Cuahutle D., Santillan R., and Farfán N. Can. J. Chem. 79 (2001) 1229-1237
45. López-Ruiz H., Mera-Moreno I., Rojas-Lima S., Santillan R., and Farfán N. Tetrahedron Lett. 49 (2008) 1674-1677
46. Abreu A., Alas S.J., Beltán H.I., Santillan R., and Farfán N. J. Organomet. Chem. 691 (2006) 337-348
47. Rodríguez M., Ochoa M.E., Rodríguez C., Santillan R., Barba V., and Farfán N. J Organomet. Chem. 692 (2007) 2425-2435
48. Rodríguez M., Ochoa M.E., Santillan R., Farfán N., and Barba V. J. Organomet. Chem. 690 (2005) 2975-2988
49. 3): δ 10.87 (s, 1H, OH), 8.70 (d, 1H, J = 2.4 Hz, H-7′), 8.32 (dd, 1H, J = 2.4 Hz, J = 8.7 Hz, H-5′), 8.04-8.00
50. Crystallographic data (excluding structure factors) for the structures in this Letter have been deposited with the Cambridge Crystallographic Data Centre as a Supplementary Publication Numbers, CCDC 713665 No. for 3a Copy of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].
51. Brewster K., Chittenden R.A., Harrison J.M., and Inch T.D. J. Chem. Soc., Perkin Trans. 1 (1976) 1291-1296
52. Stokker G. J. Org. Chem. 48 (1983) 2613-2615