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Synthesis, Spectroscopy and X-Ray Crystal Structure of 9-Methyl-3-Thiophen-2-Yl-Thieno [3, 2-e] [1, 2, 4] Triazolo [4, 3-c] Pyrimidine-8-Carboxylic Acid Ethyl Ester
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American Journal of Analytical Chemistry·Volume 02 (2011)·Pages 371–375·Published 8 July 2011·DOI10.4236/ajac.2011.23045
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Abstract
The Preparation of 9-Methyl-3-thiophen-2-yl-thieno [3, 2-e] [1, 2, 4] triazolo [4, 3-c] pyrimi-dine-8-carboxylic acid ethyl ester is described. Elemental analysis, IR spectrum, <SUP>1</SUP>H NMR, <SUP>13</SUP>C NMR and X-ray crystal structure analyses were carried out to determine the composition and molecular structure of the title compound. There are two independent molecules in the asymmetric unit exhibiting intermolecular C-H…N, C-H…O interactions with additional π-π interaction that further helps in stabilizing the supramolecular structure. The results showed that the proposed method for synthesis is simple, precise and accurate which was further confirmed by crystal structure analysis.
KeywordsThieno-Triazolo-Pyrimidine DerivativeCharacterizationX-Ray Crystallographic AnalysisC-H…NC-H…O and π-π Weak Interactions
- B. Roth, C. Cheng, “Progress in Medicinal Chemistry”, (Eds. G. P. Ellis and G. B. West), Elsevier Biomedical Press, New York, 1982.
- D. J. Brown, “Pyrimidines and their Benzo Derivatives, in Comprehensive Heterocyclic Chemistry,” (Eds. A. R. Katritzky and C. W. Rees), Pergamon Press, Oxford, 1984.
- C. R. Petrie, H. B. Cottam, P. A. Mckernan, R. K. Robins and G. R. Revankar, “Synthesis and Biological Activity of 6-Azacadeguomycin and Certain 3,4,6-Trisubstituted Ppyrazolo[3, 4-d]Pyrimidine Ribonucleosides,” Journal of Medicinal Chemistry, Vol. 28, No. 8, 1985, pp. 1010- 1016. doi:10.1021/jm00146a007
- M. N. Nasr, M. M. Gineinah, “Pyrido[2, 3-d]Pyrimidines and Pyrimido[5',4':5,6]Pyrido[2, 3-d]Pyrimidines as New Antiviral Agents: Synthesis and Biological Activity,” Archiv der Pharmazie Chemistry in Life Science, Vol. 335, No. 6, 2002, pp. 289-295. doi:10.1002/1521-4184(200208)335:6 3.0.CO;2-Z
- P. G Baraldi, M. G Pavani, M. D. Nunez, P. Brigidi, B. Vitali, R. Gambari and R. Romanoli, “Antimicrobial and Antitumor Activity of N-Heteroimmine-1,2,3-Dithiazoles and their Transformation in Triazolo-, Imidazo-, and Pyrazolopirimidines,” Bioorganic & Medicinal Chemistry, Vol. 10, No. 2, 2002, pp. 449-456. doi:10.1016/S0968-0896(01)00294-2
- S. M. Sondhi, M. Johar, S. Rajvanshi, S. G. Dastidar, R. Shukla, R. Raghubir and J. W. Lown, “Anticancer, Anti-Inflammatory and Analgesic Activity Evaluation of Heterocyclic Compounds Synthesized by the Reaction of 4-Isothiocyanato-4-Methylpentan-2-One with Substituted o-Phenylenediamines, o-Diaminopyridine and (Un) Substituted o,” Australian Journal of Chemistry, Vol. 54, 2001, pp. 69-74. doi:10.1071/CH00141
- N. S. Shetty, R. S. Lamani and I. M. Khazi, “Synthesis and Antimicrobial Activity of Some Novel Thienopyrimidines and Triazolothienopyrimidines,” Journal of Chemical Sciences, Vol. 121, No. 3, 2009, pp. 301-307. doi:10.1007/s12039-009-0034-7
- Bruker and SAINTPLUS, “Program for Data Reduction,” Bruker Axs Inc., Madison, USA, 1998.
- G. M. Sheldrick, “Program for Crystal Structure Refinement,” SHELXL97, University of G?ttingen, Germany, 1997.
- L. J. Farrugia, “ORTEP-3 for WINDOWS-A Version of ORTEP-Ⅲ with a Graphical User Interface (GUI),” Journal of Applied Crystallography, 1997, Vol. 30, No. 1, pp. 565-566. doi:10.1107/S0021889897003117
- M. Nardelli, “Ring Asymmetry Parameters from Out-of-Plane Atomic Displacements,” Acta Crystallgraphcia Section C, Vol. 39, No. 8, 1983, pp. 1141-1142. doi:10.1107/S0108270183007696