One-pot synthesis of (E)-2-arylideneindan-1-ones from the Baylis-Hillman adducts via the successive inter- and intramolecular Friedel-Crafts reactions

Bulletin of the Korean Chemical Society

Volumn 22, Issue 10, 2001, Pages 1063-1064

  Lee, Hong Jung ^a   Kim, Taek Hyeon ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

2 Arylideneindan 1 ones; Baylis Hillman adducts; Friedel Crafts reaction

Indexed keywords

2 BENZYLIDENE INDAN 1 ONE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; BENZENE DERIVATIVE; BENZYL DERIVATIVE; INDAN DERIVATIVE; SULFURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; FRIEDEL CRAFTS REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0035540423     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
2. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
3. (c) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, pp 201-350.
4. (a) Kim, J. N.; Lee, H. J.; Lee, K. Y.; Kim, H. S. Tetrahedron Lett. 2001, 42, 3737.
5. (b) Kim, J. N.; Im, Y. J.; Gong, J. H.; Lee, K. Y. Tetrahedron Lett. 2001, 42, 4195.
6. (c) Kim, J. N.; Lee, K. Y.; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 343.
7. (d) Kim, H. S.; Kim, T. Y.; Lee, K. Y.; Chung, Y. M.; Lee, H. J.; Kim, J. N. Tetrahedron Lett. 2000, 41, 2613.
8. (e) Lee, H. J.; Chung, Y. M.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2000, 21, 843.
9. (f) Lee, H. J.; Kim, H. S.; Kim, J. N. Tetrahedron Lett. 1999, 40, 4363.
10. (g) Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron Lett. 2001, 42, 85.
11. (h) Yang, K.-S.; Chen, K. Org. Lett. 2000, 2, 729.
12. (i) Chamakh, A.; Amri, H. Tetrahedron Lett. 1998, 39, 375.
13. (j) Basavaiah, D.; Kumaragurubaran, N. Tetrahedron Lett. 2001, 42, 477.
14. (a) Lee, H. J.; Seong, M. R.; Kim, J. N. Tetrahedron Lett. 1998, 39, 6223.
15. (b) Basavaiah, D.; Pandiaraju, S.; Padmaja, K. Synlett 1996, 393.
16. (c) Basavaiah, D.; Krishnamacharyulu, M.; Hyma, R. S.; Pandiaraju, S. Tetrahedron Lett. 1997, 38, 2141.
17. (d) Saib, D.; Foucaud, A.J. Chem. Res. (S) 1987, 372.
18. (e) Basavaiah, D.; Bakthadoss, M.; Reddy, G. J. Synthesis 2001, 919.
19. (a) Levai, A.; Patonay, T. J. Heterocycl. Chem. 1999, 36, 747.
20. (b) Dimmock, J. R.; Kandepu, N. M.; Nazarali, A. J.; Kowalchuk, T. P.; Motaganahalli, N.; Quail, J. W.; Mykytiuk, P. A.; Audette, G. F.; Prasad, L.; Perjesi, P.; Allen, T. M.; Santos, C. L.; Szydlowski, J.; De Clercq, E.; Balzarini, J. J. Med. Chem. 1999, 42, 1358.
21. (c) El-Rayyes, N.; AlQatami, S.; Edun, M. J. Chem. Eng. Data 1987, 32, 481.
22. (d) Turk, C. F. Ger. Offen. 2,520,171, 1975; Chem. Abstr. 1976, 84, 74261s.
23. (e) Coombs, R. V.; Houlihan, W. J. US 3,843,665, 1974; Chem. Abstr. 1975, 82, 57687b.
24. (a) Berthelette, C.; McCooye, C.; Leblanc, Y.; Trimble, L. A. J. Org. Chem. 1997, 62, 4339.
25. (b) Hassner, A.; Cromwell, N. H. J. Am. Chem. Soc. 1958, 80, 893.
26. (c) Leblanc, Y.; Dufresne, C.; Dhawan, R.; Ollerenshaw, J.; Littke, A.; Trimble, L. A.; Tsou, N. N. Can. J. Chem. 2000, 78, 784.
27. (d) Houlihan, W. J.; Shapiro, M. J.; Chin, J. A. J. Org. Chem. 1997, 62, 1529.
28. Recently, Basavaiah and Reddy have reported the synthesis of 2-arylideneindan-1-ones from the Baylis-Hillman adducts obtained from tert-butyl acrylate. Basavaiah, D.; Reddy, R. M. Tetrahedron Lett. 2001, 42, 3025.
29. 3) δ 32.43, 124.44, 126.14, 127.66, 128.90, 129.61, 130.68, 133.89, 134.57, 134.76, 135.44, 138.05, 149.62, 194.26.
30. It is interesting to note that the possible regioisomers, 4-methyl-2-benzylideneindan-1-one or 4-chloro-2-benzylideneindan-1-one, was not isolated nor detected on tlc.