Cycloaddition reactions of azomethine ylides with a 9-fluorenone-malononitrile Knöevenagel adduct

Tetrahedron Letters

Volumn 49, Issue 41, 2008, Pages 5899-5901

  Ghandi, Mehdi ^a   Tabatabaei Rezaei, Seyed Jamal ^a   Yari, Ahmad ^a   Taheri, Abuzar ^a  

^a UNIVERSITY OF TEHRAN   (Iran)

Author keywords

Azomethine ylide; Cycloaddition; Proline; Sarcosine

Indexed keywords

9 FLUORENONE MALONONITRILE; ALDEHYDE; AZOMETHINE YLIDE; MALONONITRILE; PROLINE; SARCOSINE; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; HETERONUCLEAR MULTIPLE BOND CORRELATION; KNOEVENAGEL CONDENSATION; ROENTGEN SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 50049133978     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.127     Document Type: Article

References (19)

1. Kurt V., and Anker Gothelf J. Chem. Rev. 98 (1998) 863-909
2. Coldham I., and Hufton R. Chem. Rev. 105 (2005) 2765-2809
3. Oppolzer W. Combining C-C Bonds. In: Trost B.M., Fleming I., and Paquette L.A. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford, UK (Chapter 4.1)
4. Corey E.J. Angew. Chem., Int. Ed. 41 (2002) 1650
5. March J. Advanced Organic Chemistry, Reactions, Mechanisms and Structure. 3rd ed. (1985), John Wiley & Sons
6. George B., Imad S., Achmet S.M., Francis B., and Joelle L. Org. Lett. 5 (2003) 4915-4918
7. Yu G.G., Yibo X.A., Chris K., Darold M., and Hing L.S. Tetrahedron Lett. 43 (2002) 955-957
8. Mahalingam P., and Raghavachary R. Tetrahedron Lett. 46 (2005) 7197-7200
9. Ekamabaram R., Murugavel K., and Raghavachary R. Tetrahedron Lett. 48 (2007) 1835-1839
10. Waldmann H. Synlett (1995) 133
11. Fujimori, S. Jap. Pat. Appl. 88, 2912.
12. Fujimori S. Chem. Abstr. 112 (1990) 98409
13. Ponnusamy S., Baby V., and Suchithra M. Org. Lett. 9 (2007) 4095-4098
14. Nela M., Andrew N.B., Stephan C., and Roberat W. Tetrahedron Lett. 47 (2006) 5139-5142
15. Modified procedure for the preparation of the 9-fluorenone-malononitrile adduct: To a solution of 9-fluorenone (1 mmol) in absolute ethanol (5 mL) containing 3 drops of piperidine, malononitrile (1.1 mmol) was added and the reaction mixture was stirred at room temperature for 30 min. The resulting orange precipitate was then filtered and recrystallized from ethanol to afford the product (yield 87%, mp: 230-232 °C).
16. Abdel-Rahman A.H., Keshk E.M., Hannab M.A., and El-Bady Sh.M. Bioorg. Med. Chem. 12 (2004) 2483-2488
17. Representative procedure for the preparation of fluorene spiro[9.4′]-1-N-methyl (2′-arylidene)-3′,3′-dicyano-pyrrolidine: A mixture of sarcosine (178 mg, 2.0 mmol), aldehyde (2.0 mmol), and 1 (456 mg, 2.0 mmol) in dry toluene (20 mL) containing molecular sieves (1000 mg, 3 Å) was refluxed with stirring for the appropriate time (see Scheme 2). The progress of the reaction was followed by TLC. After completion, the solvent was removed under reduced pressure and the resulting solid was recrystallized from methanol to afford a white crystalline product.
18. 3: C, 83.79; H, 5.73; N,10.47. Found: C, 83.91; H, 5.84; N, 10.67.
19. Crystallographic data for 3a have been deposited at the Cambridge Crystallographic Data Centre with the deposition number CCDC 693980. Copies of these data can be obtained free of charge via www.ccdc.ca-m.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK; Fax: +44 1223 336 033; or e-mail: deposit@ccdc.cam.ac.uk).