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Articles

Green Synthesis of Dihydropyrimidine Annulated Heterocyclic Systems Catalyzed by Nanoporous Na+-Montmorillonite Perchloric Acid and Evaluation of Their Biological Activities

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Pages 1417-1433 | Received 11 Sep 2017, Accepted 24 Nov 2018, Published online: 22 Jan 2019

References

  • R. S. Keri, A. Hiremathad, S. Budagumpi, and B. M. Nagaraja, “Comprehensive Review in Current Developments of Benzimidazole‐Based Medicinal Chemistry,” Chemical Biology & Drug Design 86 (2015): 19–65.
  • R. V. Shingalapur, K. M. Hosamani, and R. S. Keri, “Synthesis and Evaluation of In Vitro Anti-microbial and Anti-tubercular Activity of 2-Styryl Benzimidazoles,” European Journal of Medicinal Chemistry 44 (2009): 4244–48.
  • S. M. Rida, S. A. El-Hawash, H. T. Fahmy, A. A. Hazzaa, and M. M. El-Meligy, “Synthesis of Novel Benzofuran and Related Benzimidazole Derivatives for Evaluation of In Vitro Anti-HIV-1, Anticancer and Antimicrobial Activities,” Archives of Pharmacal Research 29 (2006): 826–33.
  • P. Singla, V. Luxami, R. Singh, V. Tandon, and K. Paul, “Novel Pyrazolo[3,4-d]Pyrimidine with 4-(1H-Benzimidazol-2-yl)-Phenylamine as Broad Spectrum Anticancer Agents: Synthesis, Cell Based Assay, Topoisomerase Inhibition, DNA Intercalation and Bovine Serum Albumin Studies,” European Journal of Medicinal Chemistry 126 (2017): 24–35.
  • J. B. Bariwal, A. K. Shah, M. K. Kathiravan, R. S. Somani, J. R. Jagtap, and K. S. Jain, “Synthesis and Antiulcer Activity of Novel Pyrimidylthiomethyl- and Pyrimidylsulfinylmethyl Benzimidazoles as Potential Reversible Proton Pump Inhibitors,” Indian Journal of Pharmaceutical Education and Research 42 (2008): 225–31.
  • A. T. Mavrova, D. Vuchev, K. Anichina, and N. Vassilev, “Synthesis, Antitrichinnellosis and Antiprotozoal Activity of Some Novel Thieno[2,3-d]Pyrimidin-4(3H)-Ones Containing Benzimidazole Ring,” European Journal of Medicinal Chemistry 45 (2010): 5856–61.
  • H. S. Basavaraj, G. M. Sreenivasa, E. Jayachandran, L. V. G. Nargund, and D. S. Rao, “Synthesis of Substituted Pyrimidino Imidazolinones as Antimicrobial Agents,” Indian Journal of Heterocyclic Chemistry 15 (2005): 69–70.
  • J. Balzarini and C. McGuigan, “Bicyclic Pyrimidine Nucleoside Analogues (BCNAs) as Highly Selective and Potent Inhibitors of Varicella-Zoster Virus Replication,” Journal of Antimicrobial Chemotherapy 50 (2002): 5–9.
  • B. Kumar, B. Kaur, J. Kaur, A. Parmar, R. D. Anand, and H. Kumar, “Thermal/Microwave Assisted Synthesis of Substituted Tetrahydropyrimidines as Potent Calcium Channel Blockers,” Indian Journal of Chemistry B 41 (2002): 1526–30.
  • V. A. Risley, S. Henry, M. V. Kosyrikhina, M. R. Manzanares, I. Payan, C. D. Downer, C. C. Hellmann, S. Van Slambrouck, and L. V. Frolova, “4-Amino-2-Aryl-3-cyano-1,2-Dihydropyrimido-[1,2-a] Benzimidazoles and Their Pyrimidine Analogs as New Anticancer Agents,” Chemistry of Heterocyclic Compounds 50 (2014): 185–94.
  • Z. M. Nofal, H. H. Fahmy, and H. S. Mohamed, “Synthesis, Antimicrobial and Molluscicidal Activities of New Benzimidazole Derivatives,” Archives of Pharmacal Research 25 (2002): 28–38.
  • Ibid.
  • W. Nawrocka, B. Sztuba, M. W. Kowalska, H. Liszkiewicz, J. Wietrzyk, A. Nasulewicz, M. Pełczyńska, and A. Opolski, “Synthesis and Antiproliferative Activity in Vitro of 2-Aminobenzimidazole Derivatives,” Farmaco 59 (2004): 83–91.
  • P. F. Asobo, H. Wahe, J. T. Mbafor, A. E. Nkengfack, Z. T. Fomum, E. F. Sopbue, and D. Döpp, “Heterocycles of Biological Importance. Part 5. The Formation of Novel Biologically Active Pyrimido[1, 2-a]Benzimidazoles from Allenic Nitriles and Aminobenzimidazoles,” Journal of the Chemical Society, Perkin Transactions 1, no. 4 (2001): 457–61.
  • C. G. Neochoritis, T. Zarganes-Tzitzikas, C. A. Tsoleridis, J. Stephanidou-Stephanatou, C. A. Kontogiorgis, D. J. Hadjipavlou-Litina, and T. Choli-Papadopoulou, “One-Pot Microwave Assisted Synthesis under Green Chemistry Conditions, Antioxidant Screening, and Cytotoxicity Assessments of Benzimidazole Schiff bases and Pyrimido[1,2-a]Benzimidazol-3 (4H)-Ones,” European Journal of Medicinal Chemistry 46 (2011): 297–306.
  • S. Demirayak, U. Abu Mohsen, A. C. Karaburun, “Synthesis and Anticancer and Anti-HIV Testing of Some Pyrazino[1,2-a]Benzimidazole Derivatives,” European Journal of Medicinal Chemistry 37 (2002): 255–60.
  • A. Shaabani, A. Rahmati, A. H. Rezayan, M. Darvishi, Z. Badri, and A. Sarvari, “Clean Synthesis in Water: Uncatalyzed Three‐Component Condensation Reaction of 3‐Amino‐1,2,4‐triazole or 2‐Aminobenzimidazole with Aldehyde in the Presence of Activated CH-Acids,” Molecular Informatics 26 (2007): 973–79.
  • M. V. Reddy, J. Oh, and Y. T. Jeong, “p-Toluenesulfonic Acid-Catalyzed One-Pot Synthesis of 2-Amino-4-Substituted-1,4-Dihydrobenzo[4,5]Imidazolo[1,2-a]Pyrimidine-3-Carbonitriles under Neat Conditions,” Comptes Rendus Chimie 17 (2014): 484–89.
  • B. Hemmati, S. Javanshir, and Z. Dolatkhah, “Hybrid Magnetic Irish Moss/Fe3O4 as a Nano-Biocatalyst for Synthesis of Imidazopyrimidine Derivatives,” RSC Advances 6 (2016): 50431–36.
  • L. Seyedakbari, G. M. Ziarani, A. Badiei, M. Yadavi, P. Hajiabbasi, and A. A. Soorkic, “Multicomponent Synthesis of Benzo[4,5]Imidazo[1,2-a]Pyrimidine Derivatives Using Novel Ionic Liquid Supported Nanoporous Silica and Their Antimicrobial Properties,” Revista de Chimie 64 (2013): 832–7.
  • R. Ghorbani‐Vaghei, Z. Toghraei‐Semiromi, R. Karimi‐Nami, and Z. Salimi, “One‐Pot Synthesis of Pyrimido[1,2‐a]benzimidazoles under Solvent‐Free Conditions,” Helvetica Chimica Acta 97 (2014): 979–84.
  • J. Liu, M. Lei, and L.Hu, “Thiamine Hydrochloride (VB1): An Efficient Promoter for the One-Pot Synthesis of Benzo[4,5]Imidazo[1,2-a]Pyrimidine and [1,2,4]Triazolo[1,5-a]Pyrimidine Derivatives in Water Medium,” Green Chemistry 14 (2012): 840–6.
  • H. R. Shaterian, N. Fahimi, and K. Azizi, “New Applications of Phosphoric Acid Supported on Alumina (H3PO4–Al2O3) as a Reusable Heterogeneous Catalyst for Preparation of 2,3-Dihydroquinazoline-4(1H)-Ones, 2H-Indazolo[2,1-b]Phthalazinetriones, and Benzo[4,5]Imidazo[1,2-a]Pyrimidines,” Research on Chemical Intermediates 40 (2014): 1879–98.
  • A. Shaabani, A. Rahmati, and S. Naderi, “A Novel One-Pot Three-Component Reaction: Synthesis of Triheterocyclic 4H-Pyrimido[2,1-b]Benzazoles Ring Systems,” Bioorganic & Medicinal Chemistry Letters 15 (2005): 5553–7.
  • L. Wu, F. Yan, and C. Yang, “Silica Sulfuric Acid Promoted One-Pot Synthesis of Benzo[4,5]Imidazo[1,2-a]Pyrimidine Derivatives under Solvent-Free Conditions,” Bulletin of the Chemical Society of Ethiopia 24 (2010): 417–23.
  • C. S. Yao, S. Lei, C. H. Wang, C. X. Yu, Q. Q. Shao, and S. J. Tu, “One‐Pot Three‐Component Solvent‐Free Synthesis of Benzo[4,5]Imidazo[1,2‐a]Pyrimidine Derivatives Catalyzed by Sulfamic Acid,” Chinese Journal of Chemistry 26 (2008): 2107–11.
  • M. Abedini, F. Shirini, M. Mousapour, and O. G. Jolodar, “Poly(Vinylpyrrolidonium) Perchlorate Catalyzed One-Pot Synthesis of Tricyclic Dihydropyrimidine Derivatives,” Research on Chemical Intermediates 42 (2016): 6221–9.
  • S. K. Bharadwaj, P. K. Boruah, and P. K. Gogoi, “Phosphoric Acid Modified Montmorillonite Clay: A New Heterogeneous Catalyst for Nitration of Arenes,” Catalysis Communications 57 (2014): 124–8.
  • M. Mohsenimehr, M. Mamaghani, F. Shirini, M. Sheykhan, S. Abbaspour, and L. Shafei Sabet, “One-Pot Synthesis of Novel Pyrimido[4,5-b]Quinolines and Pyrido[2,3-d:6,5d′]Dipyrimidines Using Encapsulated-γ-Fe2O3 Nanoparticles,” Journal of Chemical Sciences 127 (2015): 1895–904.
  • J. H. Clark, “Solid Acids for Green Chemistry,” Accounts of Chemical Research 35 (2002): 791–7.
  • G. B. B. Varadwaj and K. M. Parida, “Montmorillonite Supported Metal Nanoparticles: An Update on Syntheses and Applications,” RSC Advances 3 (2013): 13583–93.
  • A. S. Maryan and M. Montazer, “Natural and Organo-Montmorillonite as Antibacterial Nanoclays for Cotton Garment,” Journal of Industrial and Engineering Chemistry. 22 (2015): 164–70.
  • H. M. Elnagdy, K. Gogoi, A. A. Ali, and D. Sarma, “Claycop/Hydrazine: A New and Highly Efficient Recyclable/Reusable Catalytic System for 1,4‐Disubstituted‐1,2,3‐Triazole Synthesis under Solvent‐Free Conditions,” Applied Organometallic Chemistry 32, no. 1 (2018): e3931.
  • O. Marvi, A. Alizadeh, and S. Zarrabi, “Montmorillonite K-10 Clay as an Efficient Reusable Heterogeneous Catalyst for the Solvent-Free Microwave Mediated Synthesis of 5-Substituted 1H-Tetrazoles,” Bulletin of the Korean Chemical Society 32, no. 11 (2011): 4001–4.
  • R. Hosseinnia, M. Mamaghani, F. Shirini, and K. Tabatabaeian, “A Convenient One‐Pot Three‐Component Approach for Regioselective Synthesis of Novel Substituted Pyrazolo[1,5‐a]Pyrimidines using Fe+3‐Montmorillonite as Efficient Catalyst,” Journal of Heterocyclic Chemistry 51, no. 2 (2014): 363–7.
  • R. A. Castanheiro, M. M. Pinto, S. M. Ravo, D. C. Pinto, A. M. Silva, and A. Kijjoa, “Improved Methodologies for Synthesis of Prenylated Xanthones by Microwave Irradiation and Combination of Heterogeneous Catalysis (K10 clay) with Microwave Irradiation,” Tetrahedron 65, no. 19 (2009): 3848–57.
  • B. Temelli, D. I. Tasgin, and C. Unaleroglu, “The Reaction of N-Tosyl Imines with Heteroaromatic Compounds: A New Access to Triheteroarylmethanes,” Tetrahedron 66, no. 34 (2010): 6765–8.
  • M. Abedini, F. Shirini, and M. Mousapour, “Poly(Vinylpyrrolidinium) Perchlorate as a New and Efficient Catalyst for the Promotion of the Synthesis of Polyhydroquinoline Derivatives via Hantzsch Condensation,” Research on Chemical Intermediates 42 (2016): 2303–15.
  • D. Zareyee and B. Karimi, “A Novel and Highly Efficient Method for the Silylation of Alcohols with Hexamethyldisilazane (HMDS) Catalyzed by Recyclable Sulfonic Acid-Functionalized Ordered Nanoporous Silica,” Tetrahedron Letters 48 (2007): 1277–80.
  • G. B. B. Varadwaj, S. Rana, and K. M. Parida, “Amine Functionalized K10 Montmorillonite: A Solid Acid-Base Catalyst for the Knoevenagel Condensation Reaction,” Dalton Transactions, 42, no. 14 (2013): 5122–9.
  • H. Xing, T. Wang, Z. Zhou, and Y. Dai, “The Sulfonic Acid-Functionalized Ionic Liquids with Pyridinium Cations: Acidities and Their Acidity–Catalytic Activity Relationships,” Journal of Molecular Catalysis A: Chemical 264, no. 1–2 (2007): 53–9.
  • F. Shirini, M. Mamaghani, and S. V. Atghia, “Sulfonic Acid-Functionalized Ordered Nanoporous Na+-Montmorillonite (SANM): A Novel, Efficient and Recyclable Catalyst for the Chemoselective N-Boc Protection of Amines in Solventless Media,” Catalysis Communications 12 (2011): 1088–94.
  • F. Shirini, M. Abedini, A. Nasiri Abkenar, and B. Baghernejad, “Sulfonic Acid-Functionalized Ordered Nanoporous Na+-Montmorillonite (SANM) as an Efficient and Recyclable Catalyst for the Tetrahydropyranylation and Detetrahydropyranylation of Alcohols and Phenols,” Journal of Nanostructure in Chemistry 4 (2014): 85–90.
  • F. Shirini, M. Mamaghani, and S. V. Atghia, “Use of Nanoporous Na+-Montmorillonite Sulfonic Acid (SANM) as an Eco-Benign, Efficient and Reusable Solid Acid Catalyst for the One-Pot Synthesis of 14-aryl-14-H-Dibenzo[a,j]Xanthenes and 1,8-Dioxo-Dodecahydroxanthene Derivatives,” Journal of the Iranian Chemical Society 10 (2013): 415–20.
  • M. Mamaghani, F. Shirini, N. O. Mahmoodi, A. Azimi-Roshan, and H. Hashemlou, “A Green, Efficient and Recyclable Fe+3@K10 Catalyst for the Synthesis of Bioactive Pyrazolo[3,4-b]Pyridin-6(7H)-Ones Under ‘on Water’ Conditions,” Journal of Molecular Structure 1051 (2013): 169–76.

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