سنتز تک‌ظرف شبه چهارجزئی 8،1-دی‌اکسو-دکاهیدروآکریدین‌ها با استفاده از مایع یونی پیریدینیوم N-سولفونیک اسید هیدروژن‌سولفات

نوع مقاله : مقاله پژوهشی

نویسندگان

1 بخش شیمی، دانشگاه پیام نور، ص.پ. 4697-19395، تهران، ایران

2 گروه مهندسی شیمی، دانشگاه صنعتی همدان، ص.پ. 579-65155، همدان، ایران

چکیده

در این تحقیق، یک روش ساده و کارآمد برای سنتز 8،1-دی‌اکسو-10،9-دی‌آریل-دکاهیدروآکریدین‌ها ارائه شده است. واکنش تک ‌ظرف شبه چهارجزئی بین دایمدون، آریل‌آلدهیدها و آمین‌های آروماتیک نوع اول در حضور مایع یونی اسیدی پیریدینیوم N-سولفونیک اسید هیدروژن‌سولفات ([Py-SO3H][HSO4]) منجر به تهیه این ترکیبات با بازده بالا در زمان نسبتاً کوتاه شد.

کلیدواژه‌ها


[1] Toure B.B HDG. Natural Product Synthesis Using Multicomponent Reaction Strategies. Chem Rev. 2009;109(44):39.
 
[2] Spalding D.P CEC, Mosher H. S. HETEROCYCLIC BASIC COMPOUNDS. XV. BENZACRIDINE DERIVATIVES. J Org Chem. 1954;19:357.
 
[3] Demeunynck M CF. Interest of Acridine Derivatives in the Anticancer Chemotherapy. Curr Pharm Des. 2001;7(1703).
 
[4] Lee  H. H WWR, Ferry D. M, van Zijl P, Pullen S. M, Denny W. A. Hypoxia-Selective Antitumor Agents. 13. Effects of Acridine Substitution on the Hypoxia-Selective Cytotoxicity and Metabolic Reduction of the Bis-bioreductive Agent Nitracrine N-Oxide. J Med Chem. 1996;39:2508.
 
[5] Mohammadi Ziarani G BA, Hassanzadeh M, Mousavi S. Synthesis of 1,8-dioxo-decahydro acridine derivatives using sulfonic acid functionalized silica (SiO2-Pr-SO3H) under solvent free conditions. Arab J Chem. 2014;7:35.
 
[6] Ashry E. S. H. E ALF, Ibrahim E. S. I, Bdeewy O. K. Microwave irradiation for accelerating the synthesis of acridine and xanthene derivatives from dimedone. ARKIVOC. 2006;ii:178.
 
[7] Martin N QM, Saoane C, Mora L, Saure M, Ockoa E, Morales A. Synthesis and conformational study of acridine derivatives related to 1,4‐dihydropyridines. J Hetrocycl Chem. 1995;51:235.
 
[8] Khazaei A M-ZAR, Afshar-Hezarkhani H, Khakyzadeh V. Programming of Fe-catalyzed cascade Knoevenagel-Michael-cyclocondensation reaction: create out pseudo acridine derivatives under solvent free conditions. Eurasian Chem Commun. 2020;27.
 
[9] Khazaei A M-ZAR, Mohammadi Z, Khakyzadeh V, Afsar J. Nano-TiO2 as an Efficient Catalyst for Tandem Knoevenagel–Michael-Cyclocondensation Reaction of Dimedone with Aromatic Aldehydes and Ammonium Acetate or Aromatic Amines under Solvent-free Conditions. J Chin Chem Soc. 2016;63:265.
 
[10] Shen W WL-M, Tian H, Tang J, Yu J-J. Brønsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water. Journal of Fluorine Chemistry. 2009;130:552.
 
[11] Dabiri M BM, Arzroomchilar E. 1-Methylimidazolium triflouroacetate ([Hmim]TFA): An efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines. Catal Commun. 2008;9:939.
 
[12] Heravi M. M DF, Bamoharram F. F. Highly efficient, four-component one-pot synthesis of tetrasubstituted imidazoles using Keggin-type heteropolyacids as green and reusable catalysts. J Mol Catal A: Chem. 2007;263:112.
 
[13] Bogevig A KN, Juhl K, Zhuang W, Jorgensen K. A. Direct Organo‐Catalytic Asymmetric α‐Amination of Aldehydes-A Simple Approach to Optically Active α‐Amino Aldehydes, α‐Amino Alcohols, and α‐Amino Acids, Angew. Chem. Int. Ed.,( 2002), 41, 1790; (b) Wolkenberg, S. E., Wisnoski, D. D., Leister, W. H., Wang, Y., Zhao, Z. and Lindsley, C. W., Efficient Synthesis of Imidazoles from Aldehydes and 1,2-Diketones Using Microwave Irradiation. Org Lett. 2004;6:1453.
 
[14] Heravi M. M BK, Oskooie H. A. S, Taheri J. Synthesis of 2,4,5-triaryl-imidazoles catalyzed by NiCl2·6H2O under heterogeneous system. J Mol Catal A: Chem. 2007:263-79.
 
[15] Usyatinsky A. Y KYL. Microwave-assisted synthesis of substituted imidazoles on a solid support under solvent-free conditions. Tetrahedron Lett. 2000;41:5031.
 
[16] Zare A AF, Moosavi-Zare A. R. Beyzavi M. H, Zolfigol M. A. Synthesis, characterization and application of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient catalyst for the preparation of hexahydroquinolines. J Mol Liq. 2013;178:113.
 
[17] Zolfigol M. A KA, Moosavi-Zare A. R, Zare A, Khakyzadeh V. Rapid synthesis of 1-amidoalkyl-2-naphthols over sulfonic acid functionalized imidazolium salts. Appl Catal A Gen. 2011;400:70.
 
[18] Moosavi-Zare A. R ZMA, Zarei M, Zare A, Khakyzadeh V. Preparation, characterization and application of ionic liquid sulfonic acid functionalized pyridinium chloride as an efficient catalyst for the solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones. J Mol Liq. 2013;186:63.
 
[19]  1961-11-01 C-P-d.
 
[20] Zieve D MM, Oglivie Isla, PhD and the A. D. A. MK Editorial Team, https://medlineplus.gov/ency/article/002406.com, 2015.
 
[21] Shen W WL-M, Tian H, Tang J, Yu J-j. Brønsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed one-pot synthesis of 1,8-dioxo-decahydroacridines in water. Journal of Fluorine Chemistry. 2009;130:522.
 
[22] Wang X-S, Zhang M.-M, Jiang, H, Shi D.-Q, Tu S.-J, Wei X.-Y, Zong Z.-M. An Improved and Benign Synthesis of 9,10-Diarylacridine-1,8-dione and Indenoquinoline Derivatives from 3-Anilino-5,5-dimethylcyclohex-2-enones, Benzaldehydes, and 1,3-Dicarbonyl Compounds in an Ionic Liquid Medium. Synthesis. 2006;24:4178.
 
[23] Soliman H. A MAY, El-Mekabati A, Elmorsy S. S. SiO2/ZnCl2-Catalyzed Heterocyclic Synthesis: Green, Rapid and Efficient One-Pot Synthesis of 14-H-dibenzo [a, j]Xanthenes, 1,8-Dioxo-octahydroxanthenes and 1,8-Dioxo-Decahydroacridines Under Solvent-Free Conditions. Chem Sci Trans. 2014;3:819.
 
[24] Hasaninejad A SM, Miar M, Firoozi S. Sulfonated Polyethylene Glycol (PEG-SO3H) as Eco-Friendly and Potent Water Soluble Solid Acid for Facile and Green Synthesis of 1,8-Dioxo-Octahydroxanthene and 1,8-Dioxo-Decahydroacridine Derivatives, Synth. and React. Inorg Nano-Met Chem. 2016;46:151.
 
[25] Ghasemzadeh M. A S-GJ, Molaei H. Fe3O4 nanoparticles: As an efficient, green and magnetically reusable catalyst for the one-pot synthesis of 1,8-dioxo-decahydroacridine derivatives under solvent-free conditions. C R Chim. 2012;15:969.
 
[26] Jin T. S ZJS, Guo T. T, Wang A. Q, Li T. S. One-Pot Clean Synthesis of 1,8-Dioxo-decahydroacridines Catalyzed by p-Dodecylbenezenesulfonic Acid in Aqueous Media. Synthesis. 2004;12:2001.
 
[27] Alam M. M MAT, Assiri M. A, Ahmed S. M, Fouda A. M. A facile and efficient synthesis of 1,8-dioxodecahydroacridines derivatives catalyzed by cobalt–alanine metal complex under aqueous ethanol media. BMC Chem. 2019;13:40.
 
[28] Zeynizadeh B GM. Microwave-promoted three-component Hantzsch synthesis of acridinediones under green conditions. Curr Chem Lett. 2020;9:71.