Document Type : Original Research Article
Authors
Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Vanak, Tehran, Iran
Abstract
In this study, the cycloaddition of azidomethyl benzene with 2,2-di(prop-2-yn-1-yl)propane-1,3-diol in the presence of copper catalyst was modeled electronically and thermodynamically in the gas and two solution phases, using quantum chemistry methods. In this line, we investigated some aspects of products and their related transition states through two plausible catalytic reaction pathways, leading to the unexpected synthesis of a statistical mixture of mono and bis-triazoles, from structural and energetic viewpoints. The obtained results revealed that production of mono and bis-triazole mixture can be essentially attributed to the balance of thermochemical and kinetical factors. Additionally, we analyzed topologically the electron density through quantum theory of atoms in molecules. In this line, electron density, its laplacian and electronic energy density properties were assessed on key bond and ring critical points to explicate more clearly the origins of electronic stability in triazole and bis-triazole products and their associated transition states.
Graphical Abstract
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Keywords
- Azide-di-alkyne cycloaddition
- Density functional theory
- Copper catalysis
- Bis-triazole
- Quantum theory of atoms in molecules
Main Subjects
- Alvarez, S. Velázquez, A. San-Félix, S. Aquaro, E. De Clercq, C.F. Perno, A. Karlsson, J. Balzarini, M.J. Camarasa, 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, 37,(1994)4185-4194.
- F. Zhang, L.L. Gan, C.H. Zhou, Synthesis, antibacterial and antifungal activities of some carbazole derivatives, Bioorg. Med. Chem. Lett, 20,(2010)1881-1884.
- L. Gan, B. Fang, C.H. Zhou, Synthesis of azole-containing piperazine derivatives and evaluation of their antibacterial, antifungal and cytotoxic activities, Bull. Korean Chem. Soc, 31, (2010) 3684-3692.
- Nath, X.Q. Sulaxna, G. Song, A. Eng, Kumar, Synthesis and spectral studies of organotin(IV) 4-amino-3-alkyl-1,2,4-triazole-5-thionates: In vitro antimicrobial activity, Spectrochim. Acta Part A, 70, (2008)766-774.
- L. Wei, S. S. Zhang, J. Gao, W. H. Li, L. Z. Xu, Z.G. Yu, Synthesis and QSAR studies of novel triazole compounds containing thioamide as potential antifungal agents, Bioorg. Med. Chem, 14,(2006)7146-7153.
- S. Kallander, Q. Lu, W. Chen, T. Tomaszek, G. Yang, D. Tew, T.D. Meek, G. A. Hofmann, C.K. Schulz-Pritchard, W.W. Smith, C.A. Janson, M.D. Ryan, G.F. Zhang, K.O. Johanson, R. B. Kirkpatrick, T. F. Ho, P. W. Fisher, M. R. Mattern, R.K. Johnson, M.J. Hansbury, J.D. Winkler, K.W. Ward, D.F. Veber, S. K. Thompson, ) 4-Aryl-1,2,3-triazole: A Novel Template for a Reversible Methionine Aminopeptidase 2 Inhibitor, optimized to Inhibit angiogenesis in vivo, J. Med. Chem, 48,(2005)5644-5647.
- Pagliai, T. Pirali, E. D. Grosso, R. D. Brisco, G.C. Tron, G. Sorba, A. A. Genazzani, Rapid Synthesis of Triazole-Modified Resveratrol Analogues via click chemistry J. Med. Chem,49,(2006)467-470.
- Lee, M. Cho, S.-Y. Ko, H. -J. Youn, D. J. Baek, W. -J. Cho, C.-Y. Kang, S. Kim, Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant alpha-GalCer, J. Med. Chem,50,(2007)585-589.
- -B. Yim, I. Dijkgraaf, R. Merkx, C. Versluis, A. Eek, G.E. Mulder, D.T.S. Rijkers, O.C. Boerman, R.M.J. Liskamp, Synthesis of DOTA-Conjugated Multimeric [Tyr3]Octreotide Peptides via a Combination of Cu(I)-Catalyzed “Click” Cycloaddition and Thio Acid/Sulfonyl Azide “Sulfo-Click” Amidation and Their in Vivo Evaluation, J. Med Chem, 53,(2010)3944-3953.
- Pisaneschi, Q.-D. Nguyen, E. Shamsaei, M. Glaser, E. Robins, M. Kaliszczak, G. Smith, A.C. Spivey, E.O. Aboagye, Development of a new epidermal growth factor receptor positron emission tomography imaging agent based on the 3-cyanoquinoline core: Synthesis and biological evaluation Bioorg. Med. Chem, 18,(2010)6634-6645.
- Saito, V. Escuret, D. Durantel, F. Zoulim, R. F. Schinazic, L. A. Synthesis of 1,2,3-triazole carbanucleoside analogues of ribavirin targeting an HCV in replicon, Agrofoglio, Bioorg. Med. Chem, 11,(2003)3633-3639.
- K. Mohapatra, P.K. Maity, M. Shabab, M.I. Khan, Click chemistry based rapid one-pot synthesis and evaluation for protease inhibition of new tetracyclic triazole fused benzodiazepine derivatives. Bioorg. Med. Chem. Lett,19,(2009)5241-5245.
- O. Olomola, R. Klein, K. A. Lobb, Y. Sayed, P.T. Kaye, Towards the synthesis of coumarin derivatives as potential dual-action HIV-1 protease and reverse transcriptase inhibitors. Tetrahedron Lett, 51,(2010)6325-6328.
- D. da Silva, M. C. B. V. de Souza, I. I. P. Frugulhetti, H.C. Castro, S. L. D. Souza, T. M. L. de Souza, D. Q. Rodrigues, A. M. T. Souza, P. A. Abreu, F. Passamani, C.R. Rodrigues, V.F. Ferreira, Synthesis, HIV-RT inhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazole derivatives of carbohydrates, Eur. J. Med. Chem, 44,(2009)373-383.
- S. Costa, N. Boechat, E.A. Rangel, F. de C. da Silva, A.M.T. de Souza, C.R. Rodrigues, H. C. Castro, I.N. Junior, M.C.S. Lourenc, S. M.S.V. Wardell, V.F. Ferreira, Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives. Bioorg. Med. Chem, 14(2006)8644-8653.
- P. Tripathi, A.K. Yadav, A. Ajay, S.S. Bisht, V. Chaturvedi, S.K. Sinha, Application of Huisgen (3+ 2) cycloaddition reaction: synthesis of 1-(2, 3-dihydrobenzofuran) 2-yl-methyl [1, 2, 3]-triazoles and their antitubercular evaluations . Eur. J. Med. Chem, 45 (2010)142-148.
- Dabak, O. Sezer, A. Akar, O. Anac, Synthesis and investigation of tuberculosis inhibition activities of some 1,2,3-triazole derivatives. Eur. J. Med. Chem, 38,(2003)215-218.
- K. Singh, A.K. Yadav, B. Kumar, A. Gaikwad, S.K. Sinha, V. Chaturvedi, R.P. Tripathi, Preparation and reactions of sugar azides with alkynes: synthesis of sugar triazoles as antitubercular agents. Carbohydr. Res, 343,(2008)1153-1162.
- Gill, G. Jadhav, M. Shaikh, R. Kale, A. Ghawalkar, D. Nagargoje, M. Shiradkar, Clubbed [1,2,3] triazoles by fluorine benzimidazole: A novel approach to H37Rv inhibitors as a potential treatment for tuberculosis. Bioorg. Med. Chem. Lett, 18,(2008)6244-6247.
- L. Conte, A. Marra, A. Chambery, S.S. Gurcha, G.S. Besra, A. Dondoni, Modular Approach to Triazole-Linked 1,6-α-d-Oligomannosides to the Discovery of Inhibitors of Mycobacterium tuberculosis Cell Wall Synthetase, J. Org. Chem, 75,(2010)6326-6336.
- Q. Deng, C.X. Wei, F.N. Li, Z.G. Sun, Z.S. Quan, Design and synthesis of 10-alkoxy-5,6-dihydro-triazolo[4,3-d]benzo[f][1,4] oxazepine derivatives with anticonvulsant activity, Eur. J. Med. Chem, 45,(2010)3080-3086.
- A. Al-Omar, E.S. Al-Abdullah, I.A. Shehata, E.E. Habib, T.M. Ibrahim, A.A. ElEmam, Synthesis, antimicrobial, and anti-inflammatory activities of novel 5-(1- adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and related derivatives, Molecules, 15,(2010)2526-2550.
- Q. Fan, A.R. Katritzky, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), In Comprehensive Heterocyclic Chemistry II, vol. 4, Elsevier Science, Oxford, (1996) pp. 1-126.
- V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, A stepwise huisgen cycloaddition process: copper(I)-atalyzed regioselective “ligation” of azides and terminal alkynes. Angew. Chem. Int. Ed, 41,(2002)2596-2599.
- W. Tornoe, C. Christensen, M. Meldal, [1,2,3]- triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloa-dditions of terminal alkynes to azides, J. Org. Chem, 67,(2002)3057-3064.
- Huisgen, Kinetics and reaction mechanisms: selected examples from the experience of forty years. Pure Appl. Chem, 61,(1989)613-628.
- Huisgen, G. Szeimies, L. Möbius, 1.3-Dipolare Cycloadditionen, XXXII. Kinetik der Additionen organischer Azide an CC-Mehrfachbindungen, Chem. Ber, 100,(1967)2494-2507.
- (a) M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.E. Emmert,
A. Garmon, D.R. Graber, K.C. Grega, J.B. Hester, D.K. Hutchinson, J. Morris,
R.J. Reischer, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert,
B.H. Yagi, Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gramnegative organisms Haemophilus influenzae and Moraxella catarrhalis, J. Med. Chem, 43,(2000)953-970; (b) V. Castro, H. Rodríguez, F. Albericio, CuAAC: an efficient click chemistry reaction on solid phase, ACS Comb. Sci, 18,(2016)1-14;(c) R. Alvarez, S. Velazquez, A. SaneFelix, S. Aquaro, E. De Clercq, C.-F. Perno, A. Karlsson, J. Balzarini, M.J. Camarasa, 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, 37,(1994),4185-4194; (d) J. Totobenazara, A.J. Burke, New click chemistry methods for 1,2,3-triazoles synthesis: recent advances and applications, Tetrahedron Lett, 56,(2015)2853-2859; (e) V.K. Tiwari, B.B. Mishra, K.B. Mishra, N. Mishra, A.S. Singh, X. Chen, Cu-catalyzed click reaction in carbohydrate chemistry, Chem. Rev, 116,(2016)3086-3240. - Z-J. Zheng, D. Wang, Z. Xu, L-W. Xu, Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry, Beilstein J. Org. Chem, 11,(2015)2557-2576.
- I. Mohammed, Z.H. Abboud, A.H.O. Alghanimi, Synthesis of D-mannitol substituted ether-linked bis-1,2,3-triazoles as models of gemini surfactants, Tetrahedron Lett, 53,(2012)5081-5083.
- Ye, F. Zhang, L. Han, P. Luo, J. Yang, H. Chen, The effect of temperature on the interfacial tension between crude oil and gemini surfactant solution, Colloid Surface A, 322(1),(2008)138-141.
- Geng, X. Hu, J. Xia, X. Jia, Synthesis and surface activities of a novel di-hydroxyl-sulfate-betaine-type zwitterionic gemini surfactants , Appl Surf Sci, 271,(2013)284-290.
- Lal, A. Kumar, M. S. Pavan, C. P. Kaushik, Regioselective synthesis and antimicrobial studies of ester linked 1,4-disubstituted 1,2,3-bis-triazoles, Bioorg. Med. Chem. Lett, 22,(2012) 4353-4357.
- C. Nielsen, A.F. Larsen, F.H. Abdikadir, T. Ulven, Phenanthroline-2,9-bis-triazoles as selective G-quadruplex ligands, Eur. J. Med. Chem,72,(2014)119-126.
- D. Becke, A new mixing of Hartree–Fock and local density‐functional theories J. Chem. Phys, 98,(1993)1372-1377.
- Özen, A theoretical approach to the mechanisms of copper catalyzed furofuran and 1,2,3-triazole synthesis, PhD thesis, Istanbul Technical University (2012).
- X-H. Li, C. Zhang, X-H, Ju, Theoretical screening of bis-triazole-derived energetic salts with high properties and low sensitivity, RSC Adv, 9,(2019)26442-26449.
- Hosseinnejad, M.M. Heravi, R. Firouzi, Regioselectivity in the Sonogashira synthesis of 6-(4-nitrobenzyl)-2-phenylthiazolo[3,2-b]1,2,4 triazole: a quantum chemistry study, J. Mol. Modeling,19,( 2013)951-961.
- Hosseinnejad, M. Dinyari, Computational study on stereoselective synthesis of substituted 1H-tetrazolesvia a click reaction: DFT and QTAIM approaches, Comput. Theor. Chem, 1071,(2015)53- 60.
- Hosseinnejad, S. Mahdavian, Quantum chemistry study on regioselectivity in ruthenium catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles, Comput. Theor. Chem, 1143,(2018)29-35.
- Hosseinnejad, F. Ebrahimpour-Malmir, B. Fattahi, Computational investigations of clickderived 1, 2, 3-triazoles as keystone ligands for complexation with transition metals: a review ,RSC Advances, 8,(2018)12232-12259.
- Hosseinnejad, M.M. Heravi, M. Omrani-Pachin, Computational and Experimental
Investigations on the Synthesis and Properties of Hantzsch-type Compounds: An Overview, Curr. Org. Chem, 23,(2019)1417-1434. - M. Heravi, T. Hosseinnejad, M. Tamimi, V. Zadsirjan, M. Mirzaei, 12-Tungstoboric
acid (H5BW12O40) as an efficient Lewis acid catalyst for the synthesis of chromenopyrimidine-
2,5-diones and thioxochromen-opyrimidin-5-ones: Joint experimental and computational study, J. Mol. Struct, 1205,(2020)127598. - Zoghi, M. M. Heravi, N. Montazeri, M. Mohammadi Zeydi, T. Hosseinnejad, Preparation of an efficient catalyst through injection of CuI on modified poly
(styrene‐ co‐ maleic anhydride) and theoretical investigation of the structural and electronic properties of catalyst, Appl. Organometal Chem, 34 (2020) e5435. - Momeni, M.M Heravi, T. Hosseinnejad, M. Mirzaei, V. Zadsirjan, H5BW12O40-
Catalyzed syntheses of 1, 4-dihydropyridines and polyhydro-quinolines via Hantzsch reaction:
Joint experimental and computational studies, J. Mol. Struct, 1199 (2020),127011. - Ebrahimpour-Malamir, T. Hosseinnejad, R. Mirsafaei, M.M. Heravi, Synthesis,
characterization and computational study of CuI nanoparticles immobilized on modified poly (styrene-co-maleic anhydride) as a green, efficient and recyclable heterogeneous catalyst in the
synthesis of 1,4-disubstituted 1,2,3-triazoles via click, Appl. Organomet. Chem, 32,(2018)3913. - BaieLashaki, H. A. Oskooie, T. Hosseinnejad, M. M. Heravi, CuI nanoparticles on modified poly(styrene-co-maleic anhydride) as an effective catalyst in regioselective synthesis of
1,2,3-triazoles via click reaction: a joint experimental and computational study, J. Coord. Chem, 70,(2017)1815-1834. - Hossiennejad, M. Daraie, M.M. Heravi, N.N. Tajoddin, Computational and
Experimental Investigation of Immobilization of CuI Nanoparticles on 3-Aminopyridine Modified Poly(styrene-co-maleic anhydride) and Its Catalytic Application in Regioselective Synthesis of 1,2,3-Triazoles, J. Inorg. Organomet. Polym, 27,(2017)861-870. - M. Heravi, T. Hosseinnejad, N. Nazari, Computational investigations on structural and electronic properties of CuI nanoparticles immobilized on modified poly (styrene-co-maleic
anhydride), leading to an unexpected but efficient catalyzed synthesis of 1,4-dihydropyridine via Hantzsch pyridine synthesis Can. J. Chem, 95,(2017)530-536. - Hosseinnejad, T. Kazemi, Quantum chemical investigation on complexation of palladium with iminopyridyl ligands: Structural, thermochemical, and electronic aspects, Mol. Cryst. Liq. Cryst, 637,(2016)53-64.
- Mirsafaei, M.M. Heravi, T. Hosseinnejad, S. Ahmadi, Copper (II) nanoparticles: an
efficient and reusable catalyst in green oxidation of benzyl alcohols to benzaldehydes in water. ,Appl. Organomet. Chem, 30,(2016)823-830. - Zadsirjan, M.M. Heravi, M. Tajbakhsh, H.A. Oskooie, M. Shiri, T. Hosseinnejad, Hydroarylation of cinnamic acid with phenols catalyzed by acidic ionic liquid [H-NMP] HSO4: computational assessment on substituent effect, Res. Chem. Inter,42,(2016)6407-6422.
- Mirsafaei, M.M. Heravi, S. Ahmadi, T. Hosseinnejad, Synthesis and properties of novel reusable nano-ordered KIT-5-sulfamic acid as a heterogeneous catalyst for solvent-free synthesis of 2,4,5-triaryl-1H-imidazoles, Chem. Pap, 70,(2016)418-429.
- Mirsafaei, M.M. Heravi, Sh. Ahmadi, M. Moslemin, T. Hosseinnejad, In situ prepared copper nanoparticles on modified KIT-5 as an efficient recyclable catalyst and its applications in click reactions in water, J. Mol. Catal. A, 402,(2015)100-108.
- Khaghaninejad, M. M. Heravi, T. Hosseinnejad, H.A. Oskooie, M. Bakavoli, Regioselective synthesis of 5-substituted 1H-tetrazoles using ionic liquid [BMIM]N3 in solvent-free conditions: a click reaction, Res. Chem. Intermed, 42,(2016)1593-1610.
- O. Rodionov, V.V. Fokin, M.G. Finn, Mechanism of the ligand-free Cu-I-catalyzed azide-alkyne cycloaddition reaction, Angew. Chem. Int. Ed, 44,(2005)2210-2215.
- Himo, T. Lovell, R. Hilgraf, V.V. Rostovtsev, L. Noodleman, K.B. Sharpless, V.V. Fokin, Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermdiates, J. Am. Chem. Soc, 127,(2005)210-216.
- P. Collman, N, K, Devaraj, C.E.D. Chidsey, Clicking Functionality onto Electrode Surfaces, Langmuir, 20 (2004)1051-1053.
- 59 R.F.W. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford, UK, (1990).
- G. Truhlar, Y. Zhao, The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excitedstates, and transition elements: two new functionals and systematic testing off our M06-class
functionals and 12 other functional, Theor. Chem. Account, 120,(2008)215-241. - Barone, M. Cossi, Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model, J. Phys. Chem. A, 102,(1998)1995-2001.
- J. Hay, W.R. Wadt, Ab initio effective core potentials for molecular calculations.
Potentials for K to Au including the outermost core orbitals, J. Chem. Phys, 82,(1985)299-310. - W. Schmidt, K.K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, General Atomic and Molecular Electronic Structure System, J. Comput. Chem, 14,(1993)1347-1363.
- F. W. Bader, AIM2000 Program ver 2.0, McMaster University, Hamilton (2000)
)
