Q-Tube Assisted Green Synthesis of Bis(Azoles) and Bis(Azines) Linked to Arene Unit

References

• C. A. Lipinski, F. Lombardo, B. W. Dominy, and P. J. Feeney, “Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings,” Advanced Drug Delivery Reviews 23, no. 1–3 (1997): 3–25. doi:10.1016/S0169-409X(96)00423-1.
   Web of Science ®Google Scholar
• L. Sancineto, F. Mangiavacchi, C. Tidei, L. Bagnoli, F. Marini, A. Gioiello, J. Scianowski, and C. Santi, “Selenium-Catalyzed Oxacyclization of Alkenoic Acids and Alkenols,” Asian Journal of Organic Chemistry 6, no. 8 (2017): 988–92. doi:10.1002/ajoc.201700193.
   Web of Science ®Google Scholar
• B. Monti, C. Santi, L. Bagnoli, F. Marini, and L. Sancineto, “Zinc Halogenolates as Green Reagents,” Current Green Chemistry 3, no. 1 (2016): 68–75. doi:10.2174/2213346103666160127003716.
   Google Scholar
• N. S. Isaacs, Liquid Phase High Pressure Chemistry (Chichester: John Wiley & Sons, Inc., 1981).
   Google Scholar
• Y. Zhang and N. J. Mosey, “High Pressure Chemistry of Thioaldehydes: A First-Principles Molecular Dynamics Study,” The Journal of Chemical Physics 145, no. 19 (2016): 194506/1–194506/11. doi:10.1063/1.4967519.
   Web of Science ®Google Scholar
• J. Im, N. Yim, J. Kim, T. Vogt, and Y. Lee, “ High-Pressure Chemistry of a Zeolitic Imidazolate Framework Compound in the Presence of Different Fluids ,” Journal of the American Chemical Society 138, no. 36 (2016): 11477–80. doi:10.1021/jacs.6b07374.
   PubMed Web of Science ®Google Scholar
• E. Horvath-Bordon, R. Riedel, A. Zerr, P. F. McMillan, G. Auffermann, Y. Prots, W. Bronger, R. Kniep, and P. Kroll, “Highpressure Chemistry of Nitride-Based Materials,” Chemical Society Reviews 35, no. 10 (2006): 987–1014. doi:10.1039/b517778m.
   PubMed Web of Science ®Google Scholar
• L. M. Harwood, “High-Pressure Chemistry. Synthetic, Mechanistic and Supercritical Applications. Edited by Rudi Van Eldik and Frank- Gerrit Klarner.” Angewandte Chemie International Edition 42 (2003): 4852.
   Google Scholar
• (a) Q-tube illustrations together with exhaustive technical details can be found at the website: http://www.qlabtech.com;
   Google Scholar
  (b) D. Ball and J. Key, J. Introductory Chemistry, 1st Canadian ed. (Victoria, BC: BC Campus, 2014), https://opentextbc.ca/introductorychemistry/
   Google Scholar
• G. Turan-Zitouni, Z. A. Kaplancikli, M. T. Yildiz, P. Chevallet, and D. Kaya, “Synthesis and Antimicrobial Activity of 4-Phenyl/Cyclohexyl-5-(1-Phenoxyethyl)-3-[N-(2-Thiazolyl)Acetamido]Thio-4H-1,2,4-Triazole Derivatives,” European Journal of Medicinal Chemistry 40, no. 6 (2005): 607–13. doi:10.1016/j.ejmech.2005.01.007.
   PubMed Web of Science ®Google Scholar
• S. A. F. Rostom, H. M. A. Ashour, H. A. El Razik, A. F. El Fattah, and N. N. El-Din, “Azole Antimicrobial Pharmacophore-Based Tetrazoles: Synthesis and Biological Evaluation as Potential Antimicrobial and Anticonvulsant Agents,” Bioorganic & Medicinal Chemistry 17, no. 6 (2009): 2410–22. doi:10.1016/j.bmc.2009.02.004.
   PubMed Web of Science ®Google Scholar
• Z. Rezaei, S. Khabnadideh, K. Pakshir, Z. Hossaini, F. Amiri, and E. Assadpour, “Design, Synthesis, and Antifungal Activity of Triazole and Benzotriazole Derivatives,” European Journal of Medicinal Chemistry 44, no. 7 (2009): 3064–67. doi:10.1016/j.ejmech.2008.07.012.
   PubMed Web of Science ®Google Scholar
• A. Khalafi-Nezhad, M. N. Soltani Rad, H. Mohabatkar, Z. Asrari, and B. Hemmateenejad, “Design, Synthesis, Antibacterial and QSAR Studies of Benzimidazole and Imidazole Chloroaryloxyalkyl Derivatives,” Bioorganic & Medicinal Chemistry 13, no. 6 (2005): 1931–38. doi:10.1016/j.bmc.2005.01.014.
   PubMed Web of Science ®Google Scholar
• J. Mann, A. Baron, Y. Opoku-Boahen, E. Johansson, G. Parkinson, L. R. Kelland, and S. Neidle, “A New Class of Symmetric Bisbenzimidazole-Based DNA Minor Groove-Binding Agents Showing Antitumor Activity,” Journal of Medicinal Chemistry 44, no. 2 (2001): 138–44. doi:10.1021/jm000297b.
   PubMed Web of Science ®Google Scholar
• B. S. Holla, K. N. Poojary, B. S. Rao, and M. K. Shivananda, “New Bis-Aminomercaptotriazoles and Bis-Triazolothiadiazoles as Possible Anticancer Agents,” European Journal of Medicinal Chemistry 37, no. 6 (2002): 511–17. doi:10.1016/s0223-5234(02)01358-2.
   PubMed Web of Science ®Google Scholar
• J. L. Adams, J. C. Boehm, T. F. Gallagher, S. Kassis, E. F. Webb, R. Hall, M. Sorenson, R. Garigipati, D. E. Griswold, and J. C. Lee, “Pyrimidinylimidazole Inhibitors of p38: Cyclic N-1 Imidazole Substituents Enhance p38 Kinase Inhibition and Oral Activity,” Bioorganic & Medicinal Chemistry Letters 11, no. 21 (2001): 2867–70. doi:10.1016/s0960-894x(01)00570-4.
   PubMed Web of Science ®Google Scholar
• R. K. Ujjinamatada, A. Baier, P. Borowski, and R. S. Hosmane, “An Analogue of AICAR with Dual Inhibitory Activity against WNV and HCV NTPase/Helicase: Synthesis and In Vitro Screening of 4-Carbamoyl-5-(4,6-Diamino-2,5-Dihydro-1,3,5-Triazin-2-yl)Imidazole-1-Beta-D-Ribofuranoside,” Bioorganic & Medicinal Chemistry Letters 17, no. 8 (2007): 2285–88. doi:10.1016/j.bmcl.2007.01.074.
   PubMed Web of Science ®Google Scholar
• Tiangong Lu, Aik Wye Goh, Mingfeng Yu, Julian Adams, Frankie Lam, Theodosia Teo, Peng Li, Ben Noll, Longjin Zhong, Sarah Diab, et al, “Discovery of (E)-3-((Styrylsulfonyl)Methyl)Pyridine and (E)-2-((Styrylsulfonyl)Methyl)Pyridine Derivatives as Anticancer Agents: Synthesis, Structure–Activity Relationships, and Biological Activities,” Journal of Medicinal Chemistry 57, no. 6 (2014): 2275–91. doi:10.1021/jm4019614.
   PubMed Web of Science ®Google Scholar
• A. Raasch, O. Scharfenstein, C. Trankle, U. Holzgrabe, and K. Mohr, “Elevation of Ligand Binding to Muscarinic M(2) Acetylcholine Receptors by Bis(Ammonio)Alkane-Type Allosteric Modulators,” Journal of Medicinal Chemistry 45, no. 17 (2002): 3809–12. doi:10.1021/jm020871e.
   PubMed Web of Science ®Google Scholar
• G. Y. Yang, K. A. Oh, N. J. Park, and Y. S. Jung, “New Oxime Reactivators Connected with CH2O(CH2)nOCH2 Linker and Their Reactivation Potency for Organophosphorus Agents-Inhibited Acetylcholinesterase,” Bioorganic & Medicinal Chemistry 15, no. 24 (2007): 7704–10. doi:10.1016/j.bmc.2007.08.056.
   PubMed Web of Science ®Google Scholar
• Barbara Di Giacomo, Annalida Bedini, Gilberto Spadoni, Giorgio Tarzia, Franco Fraschini, Marilou Pannacci, and Valeria Lucini, “Synthesis and Biological Activity of New Melatonin Dimeric Derivatives,” Bioorganic & Medicinal Chemistry 15, no. 13 (2007): 4643–50. doi:10.1016/j.bmc.2007.03.080.
   PubMed Web of Science ®Google Scholar
• P. Teli, A. Sethiya, and S. Agarwal, “An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives,” ChemistrySelect 4, no. 47 (2019): 13772–787. doi:10.1002/slct.201903632.
   Web of Science ®Google Scholar
• P. Teli, N. Sahiba, A. Sethiya, J. Soni, and S. Agarwal, “Advancement in Synthetic Strategies of Bisdimedones: Two Decades Study,” Journal of Heterocyclic Chemistry 58, no. 7 (2021): 1393–407. doi:10.1002/jhet.4239.
   Web of Science ®Google Scholar
• A. Sethiya, P. Teli, A. Manhas, D. Agarwal, J. Soni, N. Sahiba, P. Jha, and S. Agarwal, “Carbon-SO3H: An Efficient Catalyst for the Synthesis of Biscoumarin under Ambient Reaction Conditions and Their In Silico Studies,” Synthetic Communications 50, no. 16 (2020): 2440–60. doi:10.1080/00397911.2020.1780613.
   Web of Science ®Google Scholar
• P. Teli, N. Sahiba, J. Soni, A. Sethiya, D. K. Agarwal, and S. Agarwal, “Exploration of Potent Multi-Target-Directed-Ligands as anti-Alzheimer's Disease Agents: A Moiety Based Review,” Mini Reviews in Medicinal Chemistry 21, no. 20 (2021): 3219–48. doi:10.2174/1389557521666210304111754.
   PubMed Web of Science ®Google Scholar
• A. A. Elassar and A. A. El-Khair, “Recent Developments in the Chemistry of Enaminones,” Tetrahedron 59, no. 43 (2003): 8463–80. doi:10.1016/S0040-4020(03)01201-8.
   Web of Science ®Google Scholar
• B. Stanovnik and J. Svete, “Synthesis of Heterocycles from Alkyl 3-(Dimethylamino)Propenoates and Related Enaminones,” Chemical Reviews 104, no. 5 (2004): 2433–80. doi:10.1021/cr020093y.
   PubMed Web of Science ®Google Scholar
• K. M. Al-Zaydi, “A Simplified Green Chemistry Approaches to Synthesis of 2-Substituted 1,2,3-Triazoles and 4-Amino-5-Cyanopyrazole Derivatives Conventional Heating Versus Microwave and Ultrasound as Ecofriendly Energy Sources,” Ultrasonics Sonochemistry 16, no. 6 (2009): 805–09. doi:10.1016/j.ultsonch.2009.02.007.
   PubMed Web of Science ®Google Scholar
• K. M. Alzaydi and T. S. Saleh, “2-Aryl Hydrazonopropanal Pharmacophores as Potent Cytotoxic Agents against Human Hepatocellular Carcinoma Cell Line,” Medicinal Chemistry Research 29, no. 2 (2020): 199–205. doi:10.1007/s00044-019-02473-8.
   Web of Science ®Google Scholar
• N. S. Ahmed, T. S. Saleh, and E.-S. H. El-Mossalamy, “An Efficiently Sonochemical Synthesis of Novel Pyrazoles, Bipyrazoles and Pyrazol-3-Ylpyrazolo[3,4-d]Pyrimidines Incorporating 1H-Benzoimidazole Moiety,” Current Organic Chemistry 17 (2013): 194–202.
   Web of Science ®Google Scholar
• Ameen Shahid, Nesreen Ahmed, Tamer Saleh, Shaeel Al-Thabaiti, Sulaiman Basahel, Wilhelm Schwieger, and Mohamed Mokhtar, “Solvent-Free Biginelli Reactions Catalyzed by Hierarchical Zeolite Utilizing a Ball Mill Technique: A Green Sustainable Process,” Catalysts 7, no. 12 (2017): 84. doi:10.3390/catal7030084.
   Google Scholar
• Katabathini Narasimharao, Ebtisam Al-Sabban, Tamer S. Saleh, Ainara Garcia Gallastegui, Almudena Celaya Sanfiz, Sulaiman Basahel, Shaeel Al-Thabaiti, Abdulrahman Alyoubi, Abdullah Obaid, and Mohamed Mokhtar, “Microwave Assisted Efficient Protocol for the Classic Ullmann Homocoupling Reaction Using Cu-Mg-Al Hydrotalcite Catalysts,” Journal of Molecular Catalysis A: Chemical 379 (2013): 152–62. doi:10.1016/j.molcata.2013.08.013.
   Google Scholar
• Tamer S. Saleh, Katabathini Narasimharao, Nesreen S. Ahmed, Sulaiman N. Basahel, Shaeel A. Al-Thabaiti, and Mohamed Mokhtar, “Mg-Al Hydrotalcite as an Efficient Catalyst for Microwave Assisted Regioselective 1,3-Dipolar Cycloaddition of Nitrilimines with the Enaminone Derivatives: A Green Protocol,” Journal of Molecular Catalysis A: Chemical 367 (2013): 12–22. doi:10.1016/j.molcata.2012.11.009.
   Google Scholar
• Fatma A. Bassyouni, Tamer S. Saleh, Mahmoud M. ElHefnawi, Sherein I. Abd El-Moez, Waled M. El-Senousy, and Mohamed E. Abdel-Rehim, “Synthesis, Pharmacological Activity Evaluation and Molecular Modeling of New Polynuclear Heterocyclic Compounds Containing Benzimidazole Derivatives,” Archives of Pharmacal Research 35, no. 12 (2012): 2063–75. doi:10.1007/s12272-012-1204-6.
   PubMed Web of Science ®Google Scholar
• M. F. Mady, T. S. Saleh, A. A. El-Kateb, N. M. Abd El-Rahman, and S. I. Abd El-Moez, “Microwave-Assisted Synthesis of Novel Pyrazole and Pyrazolo[3,4-d]Pyridazine Derivatives Incorporating Diaryl Sulfone Moiety as Potential Antimicrobial Agents,” Research on Chemical Intermediates 42, no. 2 (2016): 753–69. doi:10.1007/s11164-015-2054-x.
   Web of Science ®Google Scholar
• I. H. A. E. Maksod, and T. S. Saleh, “The Use of Nano Supported Nickel Catalyst in Reduction of p-Nitrophenol Using Hydrazine as Hydrogen Donor,” Green Chemistry Letters and Reviews 3, no. 2 (2010): 127–34. doi:10.1080/17518251003596143.
   Web of Science ®Google Scholar
• T. S. Saleh, N. M. Abd El-Rahman, and R. S. A. Assaker, “Microwave Promoted a Green Protocol for Solvent Free Synthesis of 1,5-Benzothiazepine and [1,3,4]-Thiadiazepine Derivatives Incorporating Thiophene Moiety,” Green Chemistry Letters and Reviews 5, no. 3 (2012): 315–20. doi:10.1080/17518253.2011.628953.
   Web of Science ®Google Scholar
• A. S. Al-Bogami, T. S. Saleh, A. E. M. Mekky, and M. R. Shaaban, “Microwave Assisted Regioselective Synthesis and 2D-NMR Studies of Novel Azoles and Azoloazines Utilizing Fluorine-Containing Building Blocks,” Journal of Molecular Structure 1121 (2016): 167–79. doi:10.1016/j.molstruc.2016.05.064.
   Web of Science ®Google Scholar
• A. E. M. Mekky, T. S. Saleh, and A. S. Al-Bogami, “Synthesis of Novel Pyrazoles Incorporating a Phenothiazine Moiety: Unambiguous Structural Characterization of the Regioselectivity in the 1,3-Dipolar Cycloaddition Reaction Using 2D HMBC NMR Spectroscopy,” Tetrahedron 69, no. 33 (2013): 6787–98. doi:10.1016/j.tet.2013.06.028.
   Web of Science ®Google Scholar
• P. Gamez, R. H. Steensma, W. L. Driessen, and J. Reedijk, “Copper(II) Compounds of the Planar-Tridentate Ligand 2,6-Bis(Pyrazol-3-yl)Pyridine,” Inorganica Chimica Acta 333, no. 1 (2002): 51–56. doi:10.1016/S0020-1693(02)00754-5.
   Google Scholar
• Y. I. Lin and S. A. Lang, Jr, “Novel Two Step Synthesis of Pyrazoles and Isoxazoles from Aryl Methyl Ketones,” Journal of Heterocyclic Chemistry 14, no. 2 (1977): 345–47. doi:10.1002/jhet.5570140240.
   Web of Science ®Google Scholar
• A. K. Pleier, H. Glas, M. Grosche, P. Sirsch, and W. R. Thiel, “Microwave Assisted Synthesis of 1-Aryl-3-Dimethylaminoprop-2-Enones: A Simple and Rapid Access to 3 (5)-Arylpyrazoles,” Synthesis 2001, no. 01 (2001): 0055–0062. doi:10.1055/s-2001-9761.
   Google Scholar
• E. Bejan, H. A. Haddou, J. C. Daran, and G. G. A. Balavoine, “The Reaction of Enaminones with Carboxamidines: A Convenient Route for the Synthesis of Polyaza Heterocycles,” Synthesis 1996, no. 08 (1996): 1012–18. doi:10.1055/s-1996-4330.
   Google Scholar
• A. Z. A. E. B. Hassanien, “2, 6-Bis [3-N,N-Dimethylamino-1-Oxopropen-1-Yl] Pyridine as a Building Block in Heterocyclic Synthesis: Synthesis of 2,2′:6′,2″-Terpyridines and 2,6-Bi [Pyrazolyl, Isoxazolyl, Diazepinyl, Pyrazolo [5, 1-a] Pyrimidinyl and Pyrazolo-[4,3-D] Pyridazinyl] Pyridines,” Journal of Chemical Research 2004, no. 8 (2004): 536–40. doi:10.3184/0308234042563901.
   Google Scholar