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 CSTA  Vol.2 No.4 , December 2013
Synthesis, Characterization, Crystal Studies of (E)-3-(3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl) Acrylaldehyde
Abstract: We have synthesized and developed single crystals of the title compound (E)-3-(3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl) acrylaldehyde, which is a key intermediate of anti-cholesterol fluvastatin drug. It crystallized under orthorhombic system with a space group Pna21. The dihedral angle between the indole mean plane and 4-F-phenyl ring was observed to be 111.5 (3)° in the title molecule. Further, strong hydrogen bonds were not found in the crystal structure.
Cite this paper: V. Kalalbandi and J. Seetharamappa, "Synthesis, Characterization, Crystal Studies of (E)-3-(3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl) Acrylaldehyde," Crystal Structure Theory and Applications, Vol. 2 No. 4, 2013, pp. 148-154. doi: 10.4236/csta.2013.24020.
References

[1]   R. J. Sundberg, “Indoles,” Academic Press, New York, 1996.

[2]   F. R. de sa alves, E. Z. Barreiro and C. A. M. Fraga, “From Nature to Drug Discovery: The Indole Scaffold as a Privileged Structure,” Mini-Reviews in Medicinal Chemistry, Vol. 9, No. 7, 2009, pp. 782-793.
http://dx.doi.org/10.2174/138955709788452649

[3]   N. K. Kaushik, N. Kaushik, P. Attri, N. Kumar, C. H. Kim, A. K. Verma and E. H. Choi, “Biomedical Importance of Indoles,” Molecules, Vol. 18, No. 6, 2013, pp. 6620-6662. http://dx.doi.org/10.3390/molecules18066620

[4]   D. A. Horton, G. T. Bourne and M. L. Smythe, “The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Structures,” Chemical Reviews, Vol. 103, No. 3, 2003, pp. 893-930.
http://dx.doi.org/10.1021/cr020033s

[5]   D. M. Wang, M. N. Sun and G. Liu, “Substituent Diversity-Directed Synthesis of Indole Derivatives,” Journal of Combonatorial Chemistry, Vol. 11, No. 4, pp. 556-575.
http://dx.doi.org/10.1021/cc800198p

[6]   V. Sharma, P. Kumar and D. Pathak, “Biological Importance of the Indole Nucleus in Recent Years: A Comprehensive Review,” Journal of Heterocyclic Chemistry, Vol. 47, No. 3, 2010, pp. 491-502.
http://dx.doi.org/10.1002/jhet.349

[7]   S. Rossiter, L. K. Folkes and P. Wardman, “Halogenated Indole-3-Acetic Acid as Oxidatively Activated Prodrugs with Potential for Targeted Cancer Therapy,” Bioorganic and Medicinal Chemistry Letters, Vol. 12, No. 2002, pp. 2523-2526.
http://dx.doi.org/10.1016/S0960-894X(02)00505-X

[8]   E. Abele, R. Abele, O. Dzenitis and E. Lukevics, “Indole and Isatin Oximes: Synthesis, Reactions and Biological Activity,” Chemistry of Heterocyclic Compounds, Vol. 39, No. 1, 2003, pp. 3-35.
http://dx.doi.org/10.1023/A:1023008422464

[9]   H. Panwar, R. S. Verma, V. K. Srivastava and A. Kumar, “Synthesis of Some Substituted Azetidinonyl and Thiazolidinonyl-1,3,4-thiadiazino[6,5-b]indoles as Prospective Antimicrobial Agents,” Indian Journal of Chemistry, Vol. 45B, No. 9, 2006, pp. 2099-2104.

[10]   R. E. Walkup and J. Linder, “2-Formylation of 3-Arylindoles,” Tetrahedron Letters, Vol. 26, No. l8, 1985, pp. 2155-2158.
http://dx.doi.org/10.1016/S0040-4039(00)98949-4

[11]   G. T. Lee, J. C. Amedio Jr., R. Underwood, K. Prasad and O. Repic, “Vinylformylation Utilizing Propeniminium Salts,” Journal of Organic Chemistry, Vol. 57, No. 11, 1992, pp. 3250-3252.
http://dx.doi.org/10.1021/jo00037a055

[12]   G. M. Sheldrick, “A Short History of SHELX,” Acta Crystallographica Section A, Vol. A64, 2008, pp. 112-122. http://dx.doi.org/10.1107/S0108767307043930

[13]   R. Senthamizhselvi, G. Bhaskar, P. R. Sheshadri, P. T. Perumal and K. Illangovan, “3-(1,2-Di-p-tolylvinyl)-2-methyl-1H-indole,” Acta Crystallographica Section E, Vol. E68, 2012, p. o1815.
http://dx.doi.org/10.1107/S1600536812021617

 
 
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