Reaction between triphenylphosphine, diaroylacetylenes and arylidenemalononitriles: a novel and simple synthesis of 3-aroyl-2,5-diaryl-2,4-cyclopentadiene-1,1-dicarbonitriles

Tetrahedron Letters

Volumn 49, Issue 6, 2008, Pages 945-947

  Adib, Mehdi ^a   Sayahi, Mohammad Hosein ^a   Mahernia, Shabnam ^a   Zhu, Long Guan ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

3 Aroyl 2,5 diaryl 2,4 cyclopentadiene 1,1 dicarbonitriles; Arylidenemalononitriles; Diaroylacetylenes; Triphenylphosphine

Indexed keywords

2,4 CYCLOPENTADIENE 1,1 DICARBONITRILE DERIVATIVE; AMPHOLYTE; CYCLOPENTADIENE DERIVATIVE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 37849008943     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.018     Document Type: Article

References (41)

1. Okuda J. Top. Curr. Chem. 160 (1991) 97-145
2. Halterman R.L. Chem. Rev. 92 (1992) 965-994
3. Fringuelli F., and Taticchi A. Dienes in the Diels-Alder Reaction (1990), John Wiley & Sons, New York
4. Macomber D.W., Hart W.P., and Rausch M.D. Adv. Organomet. Chem. 21 (1982) 1-55
5. Himeda Y., Yamataka H., Ueda I., and Hatanaka M. J. Org. Chem. 62 (1997) 6529-6538
6. Nair V., Menon R.S., Beneesh P.B., Sreekumar V., and Bindu S. Org. Lett. 6 (2004) 767-769
7. Funami H., Kusama H., and Iwasawa N. Angew. Chem., Int. Ed. 46 (2007) 909-911
8. Lee J.H., and Toste F.D. Angew. Chem., Int. Ed. 46 (2007) 912-914
9. Garner C.M., and Prince M.E. Tetrahedron Lett. 35 (1994) 2463-2464
10. Zair T., Santelli-Rouvier C., and Santelli M. Tetrahedron 49 (1993) 3313-3324
11. Baird M.S., and Jefferies I. Tetrahedron Lett. 27 (1986) 2493-2496
12. Flynn B.L., Funke F.J., Silveira C.C., and de Meijere A. Synlett (1995) 1007-1010
13. Koschinsky R., Köhli T.-P., and Mayr H. Tetrahedron Lett. 29 (1988) 5641-5644
14. Zhou S.L., Yan B., and Liu Y.H. J. Org. Chem. 70 (2005) 4006-4012
15. Takahashi T., Xi Z.F., Kotora M., Xi C.J., and Nakajima K. Tetrahedron Lett. 37 (1996) 7521-7524
16. Xi Z.F., and Li P.X. Angew. Chem., Int. Ed. 39 (2000) 2950-2952
17. Takahashi T., Sun W.-H., Xi C., and Kotora M. Chem. Commun. (1997) 2069-2070
18. Takahashi T., Xi Z., Kotora M., Xi C., and Nakajima K. Tetrahedron Lett. 37 (1996) 7521-7524
19. Duan Z., Sun W.H., Liu Y.H., and Takahashi T. Tetrahedron Lett. 41 (2000) 7471-7474
20. Wang C., Mao G.L., Wang Z.H., and Xi Z.F. Eur. J. Org. Chem. (2007) 1267-1273
21. Fang H.Y., Li G.T., Mao G.L., and Xi Z.F. Chem. Eur. J. 10 (2004) 3444-3450
22. Adib M., Mohammadi B., Mahdavi M., Abbasi A., and Riazati Kesheh M. Synlett (2007) 2497-2500
23. Adib M., Aali Koloogani S., Abbasi A., and Bijanzadeh H.R. Synthesis (2007) 3056-3060
24. Adib M., Sayahi M.H., Ziyadi H., Bijanzadeh H.R., and Zhu L.-G. Tetrahedron 63 (2007) 11135-11140
25. Adib M., Mahdavi M., Alizadeh Noghani M., and Bijanzadeh H.R. Tetrahedron Lett. 48 (2007) 8056-8059
26. Adib M., Sheibani E., Mostofi M., Ghanbary K., and Bijanzadeh H.R. Tetrahedron 62 (2006) 3435-3438
27. Adib M., Mahdavi M., Mahmoodi N., Pirelahi H., and Bijanzadeh H.R. Synlett (2006) 1765-1767
28. Adib M., Ghanbary K., Mostofi M., and Bijanzadeh H.R. Tetrahedron 61 (2005) 2645-2648
29. 2), 111.55 (CN), 125.90, 128.56, 128.86 and 129.08 (4CH), 129.34 (C), 129.47 and 129.54 (2CH), 129.59 (C), 130.13, 130.35, 132.32 and 134.35 (4CH), 134.96, 140.60, 141.38 and 144.13 (4C), 192.05 (C{double bond, long}O).
30. 2 = 0.135. CCDC 662538 contains the supplementary crystallographic data for this Letter. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
31. Cobridge D.E.C. Phosphorus, An Outline of the Chemistry, Biochemistry and Uses. 5th ed. (1955), Elsevier, Amsterdam
32. In: Engel R. (Ed). Synthesis of Carbon-Phosphorus Bonds (1988), CRC Press, Boca Raton
33. Cadogan J.I.G. Organophosphorus Reagents in Organic Synthesis (1979), Academic Press, New York
34. Johnson A.W. Ylides and Imines of Phosphorus (1993), Wiley, New York
35. Johnson A.W. Ylide Chemistry (1966), Academic Press, New York
36. Zbiral E. Synthesis (1974) 775-797
37. Becker K.B. Tetrahedron 36 (1980) 1717-1745
38. Ferrer P., Avendano C., and Sollhuber M. Liebigs Ann. Chem. (1995) 1895-1899
39. Kolodiazhnyi O.I. Russ. Chem. Rev. 66 (1997) 225-254
40. Bestmann H.J., and Vostrowsky O. Top. Curr. Chem. 109 (1983) 85-163
41. Bestmann H.J., and Zimmermann R. Top. Curr. Chem. 20 (1971) 1-141