Citation: AHMED Muhammad Naeem, YASIN Khawaja Ansar, KHAN Bilal Ahmad, RIAZ Muhammad, LO Kong Mun, NASEER Muhammad Moazzam, ARSHAD Ifzan, IRSHAD Muhammad. One-pot Synthesis, Characterization and Crystal Structure Determination of Novel 1,4,5-Trisubstituted 1,2,3-Triazole with Two Conformational Isomers: 1-Benzyl-5-((4-methoxyphenyl)ethynyl)-4-phenyl-1H-1,2,3-triazole[J]. Chinese Journal of Structural Chemistry, ;2016, 35(1): 55-60. doi: 10.14102/j.cnki.0254-5861.2011-0831 shu

One-pot Synthesis, Characterization and Crystal Structure Determination of Novel 1,4,5-Trisubstituted 1,2,3-Triazole with Two Conformational Isomers: 1-Benzyl-5-((4-methoxyphenyl)ethynyl)-4-phenyl-1H-1,2,3-triazole

1.
a Department of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad 13100, Pakistan;
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b Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia;
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c Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan;
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d Department of Chemistry, University of Poonch Rawalakot Azad Kashmir

Received Date: 25 May 2015
Available Online: 16 November 2015
Fund Project: This work was supported by the Higher Education Commision (HEC) (HEC)

The title compound 1-benzyl-5-((4-methoxyphenyl)ethynyl)-4-phenyl-1H-1,2,3-triazole (C₂₄H₁₉N₃O) was designed and synthesized using one-pot strategy and structural characterization was done by single-crystal X-ray diffraction, NMR, IR and MS. This compound was crystallized out from an ethanolic solution in triclinic system, space group P with a = 9.9038(9), b = 10.2928(9), c = 18.8715(19) Å, α = 103.541(6), β = 90.507(7), γ = 97.157(7)°, V = 1854.2(3) Å³, Z = 4, crystal size (mm) = 0.25 × 0.1 × 0.1 and R_int = 0.068. Its asymmetric unit contains two independent molecules. The crystal structure of the title compound is stabilized by intramolecular interactions of types C-H…N and C-H…O. Additionally, X-ray analysis reveals obvious C-H…π, π-π stacking interactions between two adjacent aromatic ring planes.
- click chemistry,
- trisubstituted triazole,
- alkyne,
- crystal structure,
- C-H…π interactions
1. [1]
  (1) Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug. Discov. Today 2003, 24, 1128-1137.
2. [2]
  (2) Kharb, R.; Sharma, P. C.; Yar, M. S. Pharmacological significance of triazole scaffold. J. Enzym. Inhib. Med. Chem. 2011, 26, 1-21.
3. [3]
  (3) Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; Clercq, E. D.; Perno, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. 1,2,3-Triazole-[2,5-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'', 2''-oxathiole 2'',2''-dioxide) (TSAO) analogs: synthesis and anti-HIV-1 activity. J. Med. Chem. 1994, 37, 4185-4194.
4. [4]
  (4) Shanmugavelan, P.; Nagarajan, S.; Sathishkumar, M.; Ponnuswamy, A.; Yogeeswari, P.; Sriram, D. Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of mycobacterium tuberculosis. Bioorg. Med. Chem. Lett. 2011, 24, 7273-7276.
5. [5]
  (5) Brockunier, L. L.; Parmee, E. R.; Ok, H. O.; Candelore, M. R.; Cascieri, M. A.; Colwell Jr, L. F.; Deng, L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J. Human β3-adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides. Bioor. Med. Chem. Lett. 2000, 1018, 2111-2114.
6. [6]
  (6) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew. Chem. Int. Ed. 2002, 114, 2708-2711.
7. [7]
  (7) Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064.
8. [8]
  (8) Mehta, V. P.; Van der Eycken, E. V. Microwave-assisted C-C bond forming cross-coupling reactions: an overview. Chem. Soc. Rev. 2011, 40, 4925-4936.
9. [9]
  (9) Stefani, H. A.; Vasconcelos, S. N.; Manarin, F.; Leal, D. M.; Souza, F. B.; Madureira, L. S.; Zukerman-Schpector, J.; Eberlin, M. N.; Godoi, M. N.; de Souza Galaverna, R. Synthesis of 5-organotellanyl-1H-1,2,3-triazoles: functionalization of the 5-position Scaffold by the sonogashira cross-coupling reaction. Eur. J. Org. Chem. 2013, 18, 3780-3785.
10. [10]
  (10) Sheldrick, G. M. Phase annealing in SHELX-90: direct methods for larger structures. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, 46, 467-473.
11. [11]
  (11) Ahmed, M. N.; Yasin, K. A.; Tahir, M. N.; Hafeez, M.; Aziz, S. Ethyl 2-[1-(3-methylbutyl)-4-phenyl-1H-1,2,3-triazol-5-yl]-2-oxoacetate. Acta Crystallogr. Sect. E 2013, 69, o1768-o1768.
12. [12]
  (12) Ahmed, M. N.; Hameed, S.; Yasin, K. A.; Arshad, I.; Ihsan-ul-Haq.; Tahir M. N. Synthesis, crystal structure and antimicrobial activity of ethyl 2-(1-cyclohexyl-4-phenyl-1H-1,2,3-triazol-5-yl)-2-oxoacetate. Chin. J. Struct. Chem. 2014, 33, 1666-1672.
13. [13]
  (13) Ahmed, M. N.; Arshad, I.; Bo, W.; Hameed, S.; Khan, B. A.; Yasin K. A.; Naseer, M. M. Molecular structure of (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)(4-bromophenyl) methanone: a combined experimental and theoretical study. Chin. J. Struct. Chem. 2014, 33, 1749-1756.
14. [14]
  (14) Saeed, A.; Arshad, I.; Flörke, U. Synthesis, crystal structure, and DFT study of N'-(2,4-dinitrophenyl)-2-fluorobenzohydrazide. J. Chem. 2013, 2013, 5.
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