154
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Preparation and Characterization of Novel Nano-cellulose-OSO3H Prepared from the Almond Shell as a Catalyst and Its Application in Synthesis of 2-Amino-3-Phenylsulfonyl-4-Aryl-4H-Benzo[h]Chromen Derivatives

, , &
Pages 6510-6522 | Received 06 Jul 2021, Accepted 16 Sep 2021, Published online: 29 Sep 2021

References

  • R. S. Bon, B. Van Vliet, N. E. Sprenkels, R. F. Schmitz, F. J. J. de Kanter, C. V. Stevens, M. Swart, F. Matthias Bickelhaupt, M. B. Groen, and R. V. A. Orru, “Multicomponent Synthesis of 2-Imidazolines,”The Journal of Organic Chemistry 70, no. 9 (2005): 3542–53.
  • J. Zhu, and H. Bienayme, Multicomponent Reactions (Germany-Weinheim: Wiley‐VCH Verlag GmbH & Co. KgaA, 2005).
  • A. Dömling, “Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry,” Chemical Reviews 106, no. 1 (2006): 17–89.
  • R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, and T. A. Keating, “Multiple-Component Condensation Strategies for Combinatorial Library Synthesis,” Accounts of Chemical Research 29, no. 3 (1996): 123–31.
  • N. K. Terret, M. Gardner, D. W. Gordon, R. J. Kobylecki, and J. Steel, “Combinatorial Synthesis - The Design of Compound Libraries and Their Application to Drug Discovery,” Tetrahedron 51, no. 30 (1995): 8135–73.
  • J. Kaur, D. Utreja, E. Malhora, N. Jain, and Sh Sharma, “Recent Developments in the Synthesis and Antimicrobial Activity of Indole and Its Derivatives,” Current Organic Chemistry 16, no. 1 (2019): 17–37.
  • S. J. Mohr, M. A. Chirigos, F. S. Fuhrman, and J. W. Pryor, “Pyran Copolymer as an Effective Adjuvant to Chemotherapy against a Murine Leukemia and Solid Tumor,” Cancer Research 35, (1975) : 3750–4.
  • A. M. El-Agrody, M. S. Abd El-Latif, N. A. El-Hady, A. H. Fakery, and A. H. Bedair, “Heteroaromatization with 4-Hydroxycoumarin Part II: Synthesis of Some New Pyrano[2,3-d] Pyrimidines, [1,2,4]Triazolo[1,5-c] Pyrimidines and Pyrimido[1,6-b]-[1,2,4]Triazine Derivatives,” Molecules 6, no. 6 (2001): 519–27.
  • A. H. Bedair, N. A. El-Hady, M. S. Abd. El-Latif, A. H. Fakery, and A. M. El-Agrody, “4-Hydroxycoumarin in Heterocyclic Synthesis Part III. Synthesis of Some New Pyrano[2,3-d] Pyrimidine, 2-Substituted[1,2,4]Triazolo[1,5-c]Pyrimidine and Pyrimido[1,6-b][1,2,4]Triazine Derivatives,” Cheminform 55, no. 11–12 (2000): 708–17.
  • A. M. El-Agrody, M. H. El-Hakim, M. S. Abd El-Latif, A. H. Fakery, E. S. M. El-Sayed, and K. A. El-Ghareab, “Synthesis of Pyrano[2,3-d]Pyrimidine and Pyrano[3,2-e]-[1,2,4]Triazolo [2,3-c]Pyrimidine Derivatives with Promising Antibacterial Activity,” Acta Pharmaceutica 50, no. 2 (2000): 111–20.
  • A. Martinez-Grau, and J. L. Marco, “Friedländer Reaction on 2-Amino-3-Cyano-4H-Pyrans: Synthesis of Derivatives of 4H-Pyran [2,3-b] Quinoline, New Tacrine Analogues,” Bioorganic & Medicinal Chemistry Letters 7, no. 24 (1997): 3165–70.
  • M. Ghashang, S. S. Mansoor, L. Shams Solaree, and A. Sharifian-Esfahani, “Multicomponent, One-Pot, Aqueous Media Preparation of Dihydropyrano[3,2-c]Chromene Derivatives over MgO Nanoplates as an Efficient Catalyst,” Iranian Journal of Catalysis 6 (2016) : 237–43.
  • S. J. Roudbaraki, S. S. Mansoor, and M. Ghashang, “Aqueous Media Synthesis of Pyrano [3,2-c] Chromen Derivatives Using Magnesium Oxide Nanoparticles as a Recyclable Catalyst,” Polycyclic Aromatic Compounds 41, no. 1 (2021): 211–22.
  • S. N. Jadhav, S. P. Patil, D. P. Sahoo, D. Rath, K. Parida, and C. V. Rode, “Organocatalytic Cascade Knoevenagel–Michael Addition Reactions: direct Synthesis of Polysubstituted 2-Amino-4H-Chromene Derivatives,”Catalysis Letters 150, no. 8 (2020): 2331–51.
  • N. G. Khaligh, O. C. Ling, T. Mihankhah, M. R. Johan, and J. J. Ching, “1,1′-Butylenebis(3-Sulfo-3H-Imidazol-1-Ium) Hydrogensulfate: A Versatile Task-Specific Ionic Liquid Catalyst for the Synthesis of 4H-Pyran Scaffolds through Non-Conventional Process,” Monatshefte Für Chemie - Chemical Monthly 150, no. 4 (2019): 655–62. no.
  • C. Medina, M. J. Santos-Martinez, A. Radomski, O. I. Corrigan, and M. W. Radomski, “Nanoparticles:pharmacological and Toxicological Significance,” British Journal of Pharmacology 150, no. 5 (2007): 552–8.
  • S. Dehghanpoor, B. Sadeghi, and M. H. Mosslemin, “Green Nano-Silica Sulfuric Acid-Catalyzed Synthesis of New 6-Amino-8-Aryl-7-(Benzenesulfonyl)-2-(Hydroxymethyl)-Pyrano[3,2-b]Pyran-4(8H)-One Derivatives,” Russian Journal of Organic Chemistry 55, no. 12 (2019): 1957–60.
  • B. Sadeghi, M. Bouslik, and M. R. Shishehbore, “Nano‑Sawdust‑OSO3H as a New, Cheap and Effective Nanocatalyst for One‑Pot Synthesis of Pyrano[2,3‑d]Pyrimidines,” Journal of the Iranian Chemical Society 12, no. 10 (2015): 1801–8.
  • A. Dehghani Ashkzari, B. Sadeghi, and S. Zavar, “TiCl4/Nano Sawdust as a Biocatalyst for the Synthesis of Ethyl 2-Amino-5-Oxo-4H,5H-Pyrano[4,3-b]Pyran-3-Carboxylates,” Polycyclic Aromatic Compounds 40, no. 4 (2020): 954–9.
  • B. Sadeghi, “Synthesis of Novel 6-Amino-2-(Hydroxymethyl)-8-Aryl-7-(Phenylsulfonyl) Pyrano[3,2-b] Pyran-4(8H)-One Derivatives Catalyzed by Nano-cellulose-OSO3H,” Research on Chemical Intermediates 45, no. 10 (2019): 4897–906.
  • E. Abyar, B. Sadeghi, and M. H. Mosslemin, “Synthesis of Novel 2-Amino-7-Methyl-4-Aryl-3- (Phenylsulfonyl)Pyrano[4,3-b]Pyran-5(4H)-One Derivatives in the Presence TiCl4 Supported on Kaolin as a Nano Catalyst,” Polycyclic Aromatic Compounds 41, no. 5 (2021): 920–8.
  • F. Manouchehri, B. Sadeghi, F. Najafi, and M. H. Mosslemin, “Preparation and Characterization of SbCl5 Supported on Coconut Shell as Nanocatalyst for the Synthesis of Novel 2-Amino-3-Phenylsulfonyl-4-Aryl-4H-Benzo[h]Chromens,” Journal of the Iranian Chemical Society 15, no. 8 (2018): 1673–83.
  • S. R. Shafe-Mehrabadi, B. Sadeghi, M. H. Mosslemin, and S. Hashemian, “Nano-Pistachio hull-OxTiCl4 − x: synthesis, Characterization and Application as an Effective and Novel Nanocatalyst for One-Pot Synthesis of Dihydropyrano[3,2-b]Chromenedione Derivatives,” Journal of the Iranian Chemical Society 18, no. 5 (2021): 1137–45.
  • M. Kamali-Gharamaleki, B. Sadeghi, M. Rouhani, and Z. Mirjafary, “Nano-Pistachio hull-OSO3H: synthesis, Characterization and Application as an Effective and Novel Nanocatalyst for One-Pot Synthesis of Dihydropyrano [3,2-b] Chromene Dione Derivatives,” Reaction Kinetics, Mechanisms and Catalysis 132, no. 1 (2021): 251–60.
  • M. A. Zolfigol, “Silica Sulfuric Acid/NaNO2 as a Novel Heterogeneous System for Production of Thionitrites and Disulfides under Mild Conditions,” Tetrahedron 57, no. 46 (2001): 9509–11.
  • (a) A. Omri, and M. Benzina, “Almond Shell Activated Carbon: Adsorbent and Catalytic Support in the Phenol Degradation,” Environmental Monitoring and Assessment 186, no. 6 (2014): 3875–90; (b) R. B. Arif, S. Karoui, K. Mougin, and A. Ghorbal, “Adsorptive Removal of Cationic and Anionic Dyes from Aqueous Solution by Utilizing Almond Shell as Bioadsorbent,” Euro-Mediterranean Journal for Environmental Integration 2, no. 1 (2017): 1–13.
  • H. Amawi, C. R. Ashby, and A. K. Tiwari, “Cancer Chemoprevention Through Dietary Flavonoids: What's Limiting?” Chinese Journal of Cancer 36, no. 1 (2017): 50–13.
  • Z. Cheng, Z. Zhang, Y. Han, J. Wang, Y. Wang, X. Chen, Y. Shao, Y. Cheng, W. Zhou, X. Lu, et al. “A Review on anti-Cancer Effect of Green Tea Catechins,” Journal of Functional Foods 74 (2020) : 104172.
  • L. S. Wang, and G. D. Stoner, “Anthocyanins and Their Role in Cancer Prevention,”Cancer Letters 269, no. 2 (2008): 281–90.
  • S. Khandelwal, Y. K. Tailor, E. Rushell, and M. Kumar, “Use of Sustainable Organic Transformations in the Construction of Heterocyclic Scaffolds,” in Green Approaches in Medicinal Chemistry for Sustainable Drug Design, edited by Banik BK (Amsterdam, North Holland: Elsevier, 2020), 245–352.
  • N. K. Shah, N. M. Shah, M. P. Patel, and R. G. Patel, “Synthesis of 2-Amino-4H-Chromene Derivatives under Microwave Irradiation and Their Antimicrobial Activity,” Journal of Chemical Sciences 125, no. 3 (2013): 525–30.
  • G. Bianchi, and A. Tava, “Synthesis of (2R)-(+)-2,3-Dihydro-2,6-Dimethyl-4H-Pyran-4-One, a Homologue of Pheromones of a Species in the Hepialidae Family,” Agricultural and Biological Chemistry 51, no. 7 (1987): 2001–2.
  • K. Hiramoto, A. Nasuhara, K. Michikoshi, T. Kato, and K. Kikugawa, “DNA Strand-Breaking Activity and Mutagenicity of 2,3-Dihydro-3,5-Dihydroxy-6-Methyl-4H-Pyran-4-One (DDMP), a Maillard Reaction Product of Glucose and Glycine,” Mutation Research 395, no. 1 (1997): 47–56.
  • X. Yu, X. Hu, and Z. Zhou, “Green and Efficient One-Pot Synthesis of 2-Amino-3-Phenylsulphonyl-4H-Chromenes under Solvent-Free Conditions,” Iranian Journal of Chemistry and Chemical Engineering 37, no. 5 (2018): 31–8.
  • K. S. Pandit, R. V. Kupwade, P. V. Chavan, U. V. Desai, P. P. Wadgaonkar, and K. M. Kodam, “Problem Solving and Environmentally Benign Approach toward Diversity Oriented Synthesis of Novel 2‑Amino-3-Phenyl (or Alkyl) Sulfonyl‑4H‑Chromenes at Ambient Temperature,” ACS Sustainable Chemistry & Engineering 4, no. 6 (2016): 3450–64.
  • A. Mazaheri, and M. Bostanian, “Synthesis and Characterization of a Novel Functionalized Magnetic Fe3O4 as a Nanocatalyst for Synthesis and Antibacterial Activities of 2-Amino-3-Phenylsulfonyl-4-Aryl-4H-Benzo[h]Chromens Derivatives and Theoretical Study on the Mechanism Using a DFT Method,”Research on Chemical Intermediates 46, no. 4 (2020): 2327–50.
  • A. Morshedi, and H. R. Shaterian, “Green Approach to Synthesis of Novel and Broad-Range Diversity of 4-(Aryl)-3-(Phenylsulfonyl)-4H-Benzo[h]Chromen-2-Amine Derivatives,” Research on Chemical Intermediates 44, no. 12 (2018): 7219–30.
  • X. Yu, and Z. Zhou, “Potassium Phthalimide Catalyzed Efficient Synthesis of 2-Amino-3-Phenylsulfonyl-4H-Chromenes under Solvent-Free Conditions,” Phosphorus, Sulfur, and Silicon and the Related Elements 193, no. 6 (2018): 387–93.
  • Z. Zhang, C. Zheng, and A. Yuan, “One-Pot Multicomponent Synthesis of 2-Amino-4-Aryl-4H-Benzo[h]Chromene Derivatives,” Polycyclic Aromatic Compounds 40, no. 5 (2020): 1397–405.
  • A. Omri, H. Ltaief, and M. Benzina, “Study of Retention of Silver Ions onto Activated Carbon Prepared from Almond Shell: Approach for the Treatment of Liquid Effluent from Radiology Journal,” Environmental Science: An Indian Journal 7, no. 4 (2012): 130–7.
  • M. Bordbar, “Biosynthesis of Ag/Almond Shell Nanocomposite as a Cost-Effective and Efficient Catalyst for Degradation of 4-Nitrophenol and Organic Dyes,” RSC Advances 7, no. 1 (2017): 180–9.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.