Abstract
New biologically active coumarin derivative, substituted xanthene-dione was synthesized by an easy, facile, cost-effective and efficient method from dimedone and diethylene glycol diacrylate without use of expensive and hazardous catalyst. The synthesis is simple, short, high-yielding and moreover does not require expensive solvents. The compound was characterized by IR, NMR and X-ray crystallography study. DFT (Density Functional Theory) calculations were performed at Becke’s three-parameter functional and Lee-Yang-Parr functional (B3LYP) level of calculation and the 6-31G++ basis set was used for ground state geometry optimization. A comparison of the selected bond lengths and bond angles of the crystal structure and theoretically optimized structure by DFT have shown good agreement. The DFT study of electron surface potential (ESP), showed a large intramolecular charge transfer efficiency of the molecule indicating optical activity of xanthene dione.
Similar content being viewed by others
References
S. Hatakeyma, N. Ochi, H. Numata, and S. Takano, J. Chem. Soc. Chem. Commun. 1202 (1988).
T. Hideo, Jpn. Tokkyo Koho JP 56005480 (1981); Chem. Abstr. 95, 80922b (1981).
R. W. Lambert, J. A. Martin, J. H. Merrett, K. E. B. Parkes, and G. J. Thomas, PCT Int. Appl. WO 9706178 (1971); Chem. Abstr. 126, 212377y (1997).
J. P. Poupelin, G. Saint-Rut, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, and R. Lacroix, Eur. J. Med. Chem. 13, 67 (1978).
J. Wichmann, K. Bleicher, E. Vieira, T. Woltering, F. Knoflach, and V. Mutel, Farmaco 57, 989 (2002).
S. Chatterrjee, M. Iqbal, J. C. Kauer, J. P. Mallamo, S. Senadhi, and S. Mallya, Bioorg. Med. Chem. Lett. 6, 1619 (1996).
R. M. Ion, Progr. Catal. 2, 55 (1997).
G. Saint-Ruf, H. T. Hieu, and J. P. Poupelin, Naturwiss 62, 584 (1975).
S. A. Hilderbrand and R. Weissleder, Tetrahedron Lett. 48, 4383 (2007).
S. M. Menchen, S. C. Benson, J. Y. L. Lam, W. Zhen, D. Sun, B. B Rosenblum, S. H. Kha, and M. Taing, U.S. Patent, 583168 (2003).
A. Banerjee and A. K. Mukherjee., Stain. Technol. 56, 83 (1981).
G. A. Reynolds, S. A. Tuccio, O. G. Peterson, and D. P. Specht, German Patent No. DE2109040 (1971).
N. Mulakayala, P. Murthy, D. Rambabu, M. Aeluri, R. Adepu, G. R. Krishna, C. M. Reddy, K. R. S. Prasad, M. Chaitanya, C. S. Kumar, M. V. Basaveswara, and M. Pal, Bioorg. Med. Chem. Lett. 22, 2186 (2012).
J. Q Wang and R. G. Harvey, Tetrahedron 58, 5927 (2002).
G. Casiraghi, G. Casnati, and M. Cornia, Tetrahedron Lett. 14, 679 (1973).
G. Casiraghi, G. Casnati, M. Catellani, and M. Cornia, Synthesis 564 (1974).
T. S. Jin, J. S. Zhang, A. Q. Wang, and T. S. Li, Synth. Commun. 35, 2339 (2005).
G. P. Hua, T. J. Li, S. L. Zhu, and X. J. Zhang, Chin. J. Org. Chem. 25, 716 (2005).
T. S. Jin, N. Qi, M. Li, L. S. Han, L. B. Liu, and T. S. Li, Asian. J. Chem. 19, 3803 (2007).
T. S. Jin, J. S. Zhang, J. C. Xio, A. Q. Wang, and T. S. Li, Synlett. 5, 866 (2004).
A. R. Khosropour, M. M. Khodaei, and H. Moghannian, Synlett. 6, 955 (2005).
B. Das, P. Thirupathi, K. Ravinder Reddy, B. Ravikanth, and L. Nagarapu, Catal. Commun. 8, 535 (2007).
B. Das, P. Thirupathi, I. Mahender, V. S. Reddy, and Y. K. Rao, J. Mol. Catal. A: Chem. 247, 233 (2006).
G. I. Shakibaei, P. Mirzaei, and A. Bazgir, Appl. Catal. A: Gen. 325, 188 (2007).
M. Dabiri, S. C. Azimi, and A. Bazgir, 62, 522 (2008).
Z. H. Zhang and X. Y. Tao, Aus. J. Chem. 61, 77 (2008).
J. J. Li, X. Y. Tao, and Z. H. Zhang, Phosphorus Sulfur 183, 1672 (2008).
G. Song, B. Wang, H. Luo, and L. Yang, Catal. Commun. 8, 673 (2007).
A. John, P. J. P. Yadav, and S. Palaniappan, J. Mol. Catal. A: Chem. 248, 121 (2006).
P. Srihari, S. S. Mandal, J. S. S. Reddy, R. S. Rao, and J. S. Yadav, Chin. Chem. Lett. 19, 771 (2008).
S. Kantevari, R. Bantu, and L. Nagarapu, J. Mol. Catal A: Chem. 269, 53 (2007).
H. Y. Lu, J. J. Li, and Z.H. Zhang, Appl. Organometal. Chem. 23, 165 (2009).
D. Kumar and J. S. Sandhu, Synth. Commun. 40, 510 (2010).
J. Li, L. Lu, and W. Su, Tetrahedron Lett. 51, 2434 (2010).
G. M. Sheldrick. Acta Crystallogr. A 64, 112 (2008).
M. N. Burnett, C. K. Johnson, Report No. ORNL-6895 (Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1996).
C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, and R. Taylor, J. Appl. Crystallogr. 41, 466 (2008).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, et al, Gaussian 03, Revision D.01 (Gaussian, Wallingford, 2004).
P. Hohenberg and W. Kohn, Phys. Rev. B 136, B864 (1964).
W. Kohn and L. Sham, Phys. Rev. A 1133, 140 (1965).
A. D. Becke, J. Chem. Phys, 98, 5648 (1993).
I. Fleming, Frontier Orbitals and Organic Chemical Reactions (Wiley, New York, 1976).
L. Sinha, O. Prasad, V. Narayan, and R. Shukla, Molecular Simul. 37, 153 (2011).
L. Pauling, The Nature of the Chemical Bond, 3d ed. (Springer, Ithaca, 1960).
K. D. Sen and C. Jorgenson, Structure and Bonding: Electronegativity, Vol. 66 (Springer, Berlin, 1987).
K. D. Sen and D. M. P. Mingos, Structure and Bonding: Chemical Hardness, Vol. 80 (Springer, Berlin, 1993).
R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules (Oxford Univ. Press, Oxford, 1989).
F. Valencia, A. H. Romero, M. Kiwi, R. Ramírez, and A. Toro-Labbé, Phys. Lett. 371, 267 (2003).
Author information
Authors and Affiliations
Corresponding author
Additional information
The article is published in the original.
Rights and permissions
About this article
Cite this article
Tarannum, N., Singh, M. Facile eco-friendly synthesis of 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-2H-xanthene 1,8(5H,9H)-dione, crystal structure and theoretical study. Crystallogr. Rep. 59, 987–992 (2014). https://doi.org/10.1134/S1063774514070190
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1063774514070190