The reaction of (N-isocyanimino)triphenylphosphorane with biacetyl in the presence of aromatic carboxylic acids: Efficient one-pot three-component reaction for the synthesis of 3-(5-aryl-1,3,4-oxadiazol-2-yl)-3-hydroxybutan-2- one derivatives

Helvetica Chimica Acta

Volumn 94, Issue 2, 2011, Pages 282-288

  Ramazani, Ali ^a   Rouhani, Morteza ^a   Rezaei, Aram ^a   Shajari, Nahid ^a   Souldozi, Ali ^b  

^a UNIVERSITY OF ZANJAN   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC CARBOXYLIC ACIDS; BIACETYL; HIGH YIELD; NEUTRAL CONDITIONS; ONE POT; ROOM TEMPERATURE; THREE COMPONENT REACTIONS;

AROMATIC COMPOUNDS; BUTANE; CARBOXYLIC ACIDS;

SYNTHESIS (CHEMICAL);

3 (5 ARYL 1,3,4 OXADIAZOL 2 YL) 3 HYDROXYBUTAN 2 ONE DERIVATIVE; BUTANE; CARBOXYLIC ACID DERIVATIVE; OXADIAZOLE DERIVATIVE; PHOSPHORANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 79951927540     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201000219     Document Type: Article

References (36)

1. 'Multicomponent Reactions', Eds. J. Zhu, H. Bienaymé, Wiley-VCH, Weinheim, 2005.
2. N. Coşkun, M. Çetin, Tetrahedron Lett. 2004, 45, 8973.
3. P. A. Wender, S. T. Handy, D. L. Wright, Chem. Ind. 1997, 765.
4. A. Dömling, Chem. Rev. 2006, 106, 17.
5. W. R. Tully, C. R. Gardner, R. J. Gillespie, R. Westwood, J. Med. Chem. 1991, 34, 2060.
6. C.-Y. Chen, C. H. Senanayake, T. J. Bill, R. D. Larsen, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1994, 59, 3738.
7. B. S. Holla, R. Gonsalves, S. Shenoy, Eur. J. Med. Chem. 2000, 35, 267.
8. M. J. Crimmin, P. J. O'Hanlon, N. H. Rogers, G. Walker, J. Chem. Soc., Perkin Trans. 1 1989, 2047.
9. U. V. Laddi, S. R. Desai, R. S. Bennur, S. C. Bennur, Ind. J. Heterocycl. Chem. 2002, 11, 319.
10. I. R. Baxendale, S. V. Ley, M. Martinelli, Tetrahedron 2005, 61, 5323.
11. S. Liras, M. P. Allen, B. E. Segelstein, Synth. Commun. 2000, 30, 437.
12. B. J. Brown, I. R. Clemens, J. K. Neesom, Synlett 2000, 131.
13. F. T. Coppo, K. A. Evans, T. L. Graybill, G. Burton, Tetrahedron Lett. 2004, 45, 3257.
14. C. T. Brain, J. M. Paul, Y. Loong, P. J. Oakley, Tetrahedron Lett. 1999, 40, 3275.
15. C. T. Brain, S. A. Brunton, Synlett 2001, 382.
16. R. Storr, 'Science of Synthesis, Houben-Weyl Methods of Molecular Transformations: Five-membered Hetarenes with Three or More Heteroatoms, Cat. 2, Vol. 13', Georg Thieme Verlag, Stuttgart, Germany, 2004.
17. V. K. Tandon, R. B. Chhor, Synth. Commun. 2001, 31, 1727.
18. S. H. Mashraqui, S. G. Ghadigaonkar, R. S. Kenny, Synth. Commun. 2003, 33, 2541.
19. F. Bentiss, M. Lagrenée, D. Barbry, Synth. Commun. 2001, 31, 935.
20. E. Jedlovská, J. Leško, Synth. Commun. 1994, 24, 1879.
21. Y. Wang, D. R. Sauer, S. W. Djuric, Tetrahedron Lett. 2006, 47, 105.
22. H. Stolzenberg, B. Weinberger, W. P. Fehlhammer, F. G. Pühlhofer, R. Weiss, Eur. J. Inorg. Chem. 2005, 4263.
23. T.-W. Chiu, Y.-H. Liu, K.-M. Chi, Y.-S. Wen, K.-L. Lu, Inorg. Chem. 2005, 44, 6425.
24. M. Adib, R. M. Kesheh, S. Ansari, R. H. Bijanzadeh, Synlett 2009, 1575.
25. A. Souldozi, A. Ramazani, N. Bouslimani, R. Welter, Tetrahedron Lett. 2007, 48, 2617.
26. A. Souldozi, A. Ramazani, Tetrahedron Lett. 2007, 48, 1549.
27. A. Ramazani, A. Souldozi, Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 3191.
28. A. Ramazani, A. Souldozi, Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 2344.
29. A. Ramazani, A. Souldozi, ARKIVOC, 2008, xvi, 235.
30. A. Ramazani, S. Salmanpour, A. Souldozi, Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 97.
31. A. Souldozi, K. Ślepokura, T. Lis, A. Ramazani, Z. Naturforsch., B 2007, 62, 835.
32. A. Ramazani, A. Rezaei, Org. Lett. 2010, 12, 2852.
33. A. Ramazani, N. Noshiranzadeh, A. Ghamkhari, K. Ślepokura, T. Lis, Helv. Chim. Acta 2008, 91, 2252.
34. A. Ramazani, A. Rezaei, A. T. Mahyari, M. Rouhani, M. Khoobi, Helv. Chim. Acta 2010, 93, 2033.
35. A. T. Mahyari, N. Shajari, A. R. Kazemizadeh, K. Ślepokura, T. Lis,A. Ramazani, Z. Naturforsch., B 2007, 62, 829.
36. P. Molina, M. J. Vilaplana, Synthesis 1994, 1197.