Introduction of Bis(methylenebis(1,4-phenylene))sulfamic Acid as a New Halogen-Free Acidic Catalyst and Its Usage in the Synthesis of New Xanthene-Based Heterocyclic Compounds

Document Type : Research Article

Authors

Department of Chemistry, University of Guilan, Rasht, I.R. IRAN

Abstract

In this work, a new sulfamic acid-based catalyst that could be used in the solid phase was synthesized using chlorosulfonic acid and methylene dianiline in a simple manner. The structure of the catalyst was characterized, and then it was used as a catalyst in the synthesis of biologically active xanthene derivatives to the evaluation of its efficiency. The mentioned catalyst showed better catalytic activity than the other reported ones from the points of simple using at solid phase and being free of environmental pollutant halogens. The results verified its capability for improving the reactions, which usually need an acidic catalyst to perform. Finally, bis(xanthenes) are synthesized using this catalyst for the first time in good yields. The structures of the new compounds were verified using FT-IR, H-NMR, and C-NMR spectroscopies.

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References

[1] Lambert R.W., Martin J.A., Merrett J.H., Parkes K. E.B., Thomas G.J., PCT Int. Appl. WO 9706178: Preparation of Pyrimidine Nucleosides as Thymidine Kinase Inhibitors and Virucides, Chem. Abstr., 126: 212377 (1997).
[2] Hideo T., Terumi J., Japan. Tokyo Koho J.P 56005480, Benzopyrano [2, 3-b] Xanthene Derivatives, Chem. Abstr., 95: 80922 (1981).
[3] Poupelin J.P., Saint-Ruf G., Lacroix R., Narcisse G., Foussard-Blanpin O.,  Uchida-Ernouf G., Synthesis and Antiinflammatory Properties of Bis(2-Hydroxy, 1-Naphthyl) Methane Derivatives, Eur. J. Med. Chem, 13: 67-71 (1978).
[4] Ion R. M., Planner A., Wiktorowicz K., Frackowiak D., The Incorporation of Various Porphyrins Into Blood Cells Measured via Flow Cytometry, Absorption and Emission Spectroscopy, Acta. Biochim. Polonica-English Edition, 45: 833-845 (1998).
[5] Menchen S.M., Benson SC., Lam J.Y.L., Zhen J.Y.L., Sun W., Rosenblum D., Khan B B.,  Taing S H., Sulfonated diarylrhodamine Dyes, U S  Patent 6583168 (2003).
[6] Knight C.G., Stephens T., Xanthene-Dye-Labelled Phosphatidylethanolamines as Probes of Interfacial pH Studies in Phospholipid Vesicles, Biochem. J., 258(3): 683-687 (1989).
[7] Malanga M., Darcsi A., Baliant M., Benkovics G., Sohajda S., Beni S., New synthetic strategies for xanthene-dye-appended cyclodextrins, Beilstein J. Org. Chem. 12, 537–548 (2016).
[8] Alcantara-Licudine J. P., Kawate M. K., Li Q. X., Method for the Analysis of Phloxine B,  Uranine, and Related Xanthene Dyes in Soil Using Supercritical Fluid Extraction and High-.Performance Liquid Chromatography, J. Agric. Food. Chem, 45(3): 766-773 (1997).
[9] Sen R. N., Sarkar N. N., The condensation of Primary Alcohols with Resorcinol and Other, Hydroxy Aromatic Compounds, J. Am. Chem. Soc, 47(4): 1079-.1091 (1925).
[10] Papini P., Cimmarusti R., The Action of Formamide and Formanilide on Naphthols and on Barbituric Acid, Gazz. Chim. Ital, 77: 142-147 (1947).
[11] Ota K., Kito T., An Improved Synthesis of Dibenzoxanthene, Bull. Chem.  Soc. Jpn., 49(4): 1167-1168 (1976).
[12] Das B., Laxminarayana K., Krishnaiah M., Srinivas Y., An Efficient and Convenient, Protocol for the Synthesis of Novel 12-aryl-or 12-alkyl-8, 9, 10, 12-tetrahydrobenzo [a], xanthen-11-one Derivatives, Synlett, (20): 3107-3112 (2007).
[13] Tietze L. F., Domino Reactions in Organic Synthesis, Chem. Rev., 96(1): 115-136 (1996).
[14] Choi H., Al-Abed S. R., Dionysiou D. D., Stathatos E., Lianos P., TiO2-Based Advanced, Oxidation Nanotechnologies for Water Purification and Reuse, Sustainability Sci.,Eng., 2: 229-254 (2010).
[15] Corma A., Current Opinion in Solid State and Materials Science, Solid Acid Catal., 2: ,63-75 (1997).
[16] Olah G.A., Prakash G.S., Sommer J. Acids up to Billions of Times Stronger than Sulfuric, Acid Have Opened up Fascinating New Areas of Chemistry, Science, 206: 13-20 (1979).
[17] Olah G.A., Prakash G.S., Sommer J., “Superacids”. Wiley-Interscience, New York. p. 34 (1985).
[18] Yamaguchi T., Recent Progress in Solid Superacid, Appl. Catal, 61(1): 1-25 (1990).
[19] Arata K., Solid Superacids. Adv. Catal, 37: 165-211 (1990).
[20] Davis B.H., Keogh R.A., Srinivasan R., Sulfated Zirconia as a Hydrocarbon Conversion Catalyst, Catal. Today, 20(2): 219-256 (1994).
[21] Song X., Sayari A., Sulfated Zirconia-Based Strong Solid-Acid Catalysts: Recent Progress, Catal. Rev, 38(3): 329-412 (1996).
[22] Corma A., Solid Acid Catalysts, Curr. Opin. Solid State Mater. Scie, .2(1): 63-75 (1997).
[23] Yadav G.D., Nair J.J., Sulfated Zirconia and Its Modified Versions as Promising Catalysts for Industrial Processes, Microporous Mesoporous Mater, 33(1): 1-48 (1999).
[24] Feller A., Lercher J.A., Chemistry and Technology of Isobutane/Alkene Alkylation, Catalyzed by Liquid and Solid acids, Adv. Catal, 48: 229-295 (2004).
[25] Corma A., Attempts to Fill the Gap Between Enzymatic, Homogeneous and Heterogeneous, Catalysis, Catal. Rev, 46(3-4): 369-417 (2004).
[26] Busca G., Acid catalysts In Industrial Hydrocarbon Chemistry, Chem. Rev., 11:,5366-5410 (2007).
[27] Bhan A., Iglesia E., A Link Between Reactivity and Local Structure in Acid Catalysis on Zeolites, Acc. Chem. Res., 41(4): 559-567 (2008).
[28] Bell A.T., Watching Catalysts at Work, Nature, 456(7219): 185-186 (2008).
[29] Reddy B.M., Patil M.K., Promoted Zirconia Solid Acid Catalysts for Organic Synthesis, Curr. Org. Chem, 12(2): 118-140 (2008).
[30] Arata K., Organic Synthesis Catalyzed by Superacidic Metal Oxides: Sulfated Zirconia and Related Compounds, Green Chem, 11(11): 1719-1728 (2009).
[31] Tamami B., Borujen K.P., Poly (vinylpyridine) Supported Reagents: A Review, Iran. Polym. J., 18(3): 191-206 (2009).
[32] Mohammadpoor-Baltork I., Moghadam M., Mirkhani V., Tangestaninejad S., Tavakoli,H.R., Highly Efficient and Green Synthesis of 14-aryl (alkyl)-14H-dibenzo [a, j], xanthene and 1, 8-Dioxooctahydroxanthene Derivatives Catalyzed by Reusable Zirconyl, Triflate [ZrO (OTf) 2] under Solvent-Free Conditions, Chin. Chem. Lett, 22(1): 9-,12 (2011).
[33] نعلبندی، احمد.، خلیلی، علی اصغر.، اﭘﻮﮐﺴﯿﺪاﺳﯿﻮن روﻏﻦ ﺳﻮﯾﺎ ﺗﻮﺳﻂ ﮐﺎﺗﺎﻟﯿﺴﺖ ﻧﺎﻫﻤﮕﻦ ﺳﯿﻠﯿﮑﺎ ﺳﻮﻟﻔﻮرﯾﮏ اﺳﯿﺪ، نشریه شیمی و مهندسی شیمی ایران، (4)33: 19 تا 29 (1393).
[34] Mahmoodi N.O., Parvizi J., Sharifzadeh B., Rassa M., Facile Regioselective Synthesis of Novel bis-Thiazole Derivatives and Their Antimicrobial Activity, Arch. ,Pharm., 346(12): 860-864 (2013).
[35] Thakur A., Sharma A., Sharma A., Efficient Synthesis of Xanthenedione Derivatives Using Cesium Salt of  Phosphotungstic Acid as a Heterogeneous And Reusable Catalyst in Water, Synth. Commun., 46: 1766–1771 (2016).
[36] Heravi M.P., Selectfluor Promoted Synthesis of 9-Aryl-1, 8-Dioxooctahydroxanthane Derivatives Under Solvent-Free Conditions, J. Iran. Chem. Soc., 6(3): ,483-488 (2009).
[37] Fan X.S., Li Y.Z., Zhang X.Y., Hu X.Y., Wang J.J., FeCl3• 6H2O Catalyzed Reaction of Aromatic Aldehydes with 5, 5-Dimethyl-1, 3-cyclohexandione in Ionic Liquids, Chin. Chem. Lett, 16: 897-899 (2005).
[38] Shirini F., Abedini M., Pourhasan R., N-sulfonic Acid Poly (4-vinylpyridinium) Chloride: A Novel Polymeric and Reusable Catalyst for the Preparation of Xanthenes Derivatives, Dyes Pigm, 99: 250-255 (2013).
[39] Horning E.C., Horning M.G., Methone Derivatives of Aldehydes, J. Org. Chem, 11(1): 95-  (1945).
[39] Shirini F., Khaligh N.G., Succinimide-N-Sulfonic Acid: an Efficient Catalyst for the Synthesis of Xanthene Derivatives Under Solvent-Free Conditions, Dyes Pigm, 95: 789-794 (2012).
[40] Bigdeli M. A., Nemati F., Mahdavinia G. H., Doostmohammadi H., Chin. Chem. Lett, 20: 1275 (2009).
[41] Seyyedhamzeh M., Mirzaei P., Bazgir A., Solvent-Free Synthesis of Aryl 14H-dibenzo [a,j] Xanthenes and 1, 8-Dioxo-Octahydro-Xanthenes Using Silica Sulfuric Acid as Catalyst, Dyes Pigm, 76: 836 (2008).
[42] Thirupathi B., Das, P., Mahender, I., Reddy V. S., Rao Y. K., Amberlyst-15: An Efficient Reusable Heterogeneous Catalyst for the Synthesis of 1, 8-Dioxo-Octahydroxanthenes and 1, 8-Dioxo-Decahydroacridines, J. Mol. Catal. A: Chem., 247: 233-239 (2006).
[43] Oskooie H. A., Tahershamsi L., Heravi M. M., Baghernejad B., Cellulose Sulfonic Acid: An Efficient Heterogeneous Catalyst for the Synthesis of 1, 8-Dioxo-Octahydroxanthenes, Eur. J. Chem, 7: 717-720 (2010).
[44] Niknam K., Damya M., 1-Butyl-3-methylimidazolium Hydrogen Sulfate [Bmim]HSO4: An Efficient Reusable Acidic Ionic Liquid for the Synthesis of 1,8-Dioxo-Octahydroxanthenes, J. Chin. Chem. Soc, 56: 659-665 (2009).
[45] Niknam K., Panahi F., Saberi D., Mohagheghnejad M., Silica-Bonded S-Sulfonic Acid as Recyclable Catalyst for the Synthesis of 1,8-Dioxo-Decahydroacridines and 1,8-Dioxo-Octahydroxanthenes, J. Heterocycl. Chem., 47: 292-300 (2010).
[46] Kokkirala S., Sabbavarapu N.M., Yadavalli V.D.N., β-Cyclodextrin Mediated Synthesis of 1, 8-Dioxooctahydroxanthenes In Water, Eur. J. Chem., 2: 272-275 (2011).
[47] Bigdeli M., Clean Synthesis of 1, 8-Dioxooctahydroxanthenes Promoted by DABCO-Bromine in Aqueous Media, Chinese Chemical Letters, 21(10): 1180-1182 (2010).
[48] Javid A., Heravi M.M., Bamoharram F.F., One-Pot Synthesis of 1, 8-Dioxo-  Octahydroxanthenes Utilizing Silica-Supported Preyssler Nano Particles as Novel and Efficient Reusable Heterogeneous Acidic Catalyst, J. Chem., 8(2): 910-916 (2011).
[50] Rashedian F., Saberi D., Khodabakhsh N., Silica-Bonded N-Propyl Sulfamic Acid: A Recyclable Catalyst for the Synthesis of 1,8-Dioxo-decahydroacridines, 1,8-Dioxo-octahydroxanthenes and Quinoxalines, J. Chin. Chem. Soc, 57(5A): 998-1006 (2010).

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