Friedel-Crafts alkylation of a cage enone: synthesis of aralkyl substituted tetracyclo[5.3.1.0[2,6].0[4,8]]undeca-9,11-diones and the formation of fascinating novel cage compounds with pyrrole and thiophene using Montmorillonite K-10

Tetrahedron Letters

Volumn 48, Issue 34, 2007, Pages 6059-6063

  James, Beena ^a   Suresh, E ^b   Nair, Mangalam S ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AROMATIC COMPOUND; CARBON; HETEROCYCLIC COMPOUND; MONTMORILLONITE; MONTMORILLONITE K 10; POLYCYCLIC HYDROCARBON; PYRROLE; TETRACYCLO[5.3.1.0 2,6 .0 4,8]UNDECA 9,11 DIONE DERIVATIVE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLAY; FRIEDEL CRAFTS REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34447641065     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.028     Document Type: Article

References (49)

1. Priefer R.P., Lee Y.J., Barrios F., Wosmick Y.H., Lebuis A.M., Farrel P.G., and Harpp D.N. J. Am. Chem. Soc. 124 (2002) 5626
2. Gallopini E., Cheblou R., Gilardi R., and Zang W. J. Org. Chem. 66 (2001) 162
3. Koga T., Ysautake M., and Shinmyozu T. Org. Lett. 3 (2001) 1419
4. Mehta G., and Vidya R. J. Org. Chem. 65 (2000) 3497
5. Giomi D., Neri R., Turchi S., and Coppini R. J. Org. Chem. 61 (1996) 6028
6. Marchand A.P. Aldrichim. Acta 28 (1995) 95
7. Osawa E., and Yonemitsu O. Carbocyclic Cage Compounds (1992), VCH, New York, NY
8. Marchand A.P. Synlett (1991) 73
9. Mehta G., and Srikrishna A. Chem. Rev. 97 (1997) 671
10. Mehta G., and Reddy A.V. J. Chem. Soc., Chem. Commun. (1984) 1058
11. Mehta G., Reddy D.S., and Reddy A.V. Tetrahedron Lett. 25 (1984) 2275
12. Mehta G., Rao K.S., Marchand A.P., and Kaya R. J. Org. Chem. 49 (1984) 3848
13. Mehta G., and Reddy A.V. J. Chem. Soc., Chem. Commun. (1981) 756
14. Marchand A.P., McKim A.S., and Kumar K.A. Tetrahedron 54 (1998) 13421
15. Marchand A.P., Reddy G.M., Zaragoza F., Bartsch R.A., and Eley M.D. Tetrahedron Lett. 34 (1993) 5377
16. Marchand A.P., Dave P.R., Rajapaksa D., Arney Jr. B.E., Flippen-Anderson J.L., Gilardi R., and George C. J. Org. Chem. 54 (1989) 1769
17. Marchand A.P., Arney Jr. B.E., and Dave P.R. J. Org. Chem. 53 (1988) 443
18. Gedenhuys W.J., Malan S.F., Bloomquist J.R., Marchand A.P., and Van der Schyf C.J. Med. Res. Rev. 25 (2005) 21
19. Eaton P.E. Angew. Chem., Int. Ed. Engl. 31 (1992) 1421
20. Michalson E.T., and Sqmurzkoviez J. Prog. Drug. Res. 33 (1989) 135
21. Grobler E., Grobler A., Van der Schyf C.J., and Malan S.F. Bioorg. Med. Chem. 14 (2006) 1176
22. Geldenhuys W.J., Malan S.F., Muruges T., Van der Schyf C.J., and Bloomquist J.R. Bioorg. Med. Chem. 12 (2004) 1799
23. Zah J., Blanche G.T., Erasmus E., and Malan S.F. Bioorg. Med. Chem. 11 (2003) 3569
24. Gante J. Angew. Chem., Int. Ed. Engl. 33 (1994) 1699
25. Giannis A., and Kolter T. Angew. Chem., Int. Ed. Engl. (1993) 1267
26. Smith M.B. Org. Synth. (1994), McGraw-Hill, New York
27. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon Press, Oxford 293
28. In: Olah G.A. (Ed). Friedel Crafts Chemistry (1973), Wiley, New York
29. Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. In Comprehensive Organic Synthesis, 1st ed.
30. Varma R.S. Tetrahedron 58 (2002) 1235
31. Cornelis A., Gerstmans A., Laszto P., Mathy A., and Ziebh I. Catal. Lett. 6 (1990) 103
32. Clark J.H., Kybett A.P., Macquarrie D.J., Barlow S.J., and Landon P. J. Chem. Soc., Chem. Commun. (1989) 1353
33. Kantam M.L., Ranganath K.V.S., Sateesh M., Kumar K.B.S., and Choudary B.M. J. Mol. Catal. A 225 (2005) 15
34. Karade N.N., Shirodkar S.G., and Potrekar R.A. J. Chem. Res. 10 (2003) 652
35. Laszto P., and Mathy A. Helv. Chim. Acta 70 (1987) 557
36. Bandini M., Melloni A., and Umani-Ronchi A. Angew. Chem., Int. Ed. 43 (2004) 550
37. Bigi F., Casiraghi G., Casnati G., Sartori G., Fava G.G., and Belicchi M.F. J. Org. Chem. 50 (1985) 18
38. Ishii A., Soloshonok V.A., and Mikami K. J. Org. Chem. 65 (2000) 1597
39. Ishii A., and Mikami K. J. Fluorine Chem. 97 (1999) 51
40. Das B., Majhi A., Banerjee J., Chowdhury N., and Venketeswarlu K. Chem. Lett. 34 (2005) 1492
41. Bahulayan D., Das S.K., and Iqbal J. J. Org. Chem. 68 (2003) 5735
42. Srinivas K.V., and Das B. J. Org. Chem. 68 (2003) 1165
43. Nair M.S., Sudhir U., Joly S., and Rath N.P. Tetrahedron 55 (1999) 7653
44. -3, respectively. CCDC 298645 contains the Supplementary data for this Letter. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: +44 1223 336 033; or deposit@ccdc.cam.ac.uk). The crystal structure revealed two independent molecules present in the asymmetric unit having almost similar conformations.
45. -3. CCDC 616644.
46. -3. CCDC 616643.
47. SAINTPLUS, Bruker AXS, Madison, Wisconsin, USA.
48. Sheldrick G.M. SADABS Program for Empirical Absorption Correction (1996), University of Gottingen, Germany
49. Sheldrick G.M. shelxs-97 and shelxl-97 (1997), University of Gottingen, Gottingen, Germany