Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Synthesis and characterization of manganese (II) catalyst loaded on SBA-15 support and its application in the synthesis of quinoxaline and pyridopyrazine heterocycles in aqueous medium

Document Type : Research Article

Authors
Farnaz Jafarpour
Mahdieh Sharifi
Razieh Nikjoo
School of Chemistry, College of Science, University of Tehran, Tehran, IRAN
Abstract
A manganese (II) catalyst loaded onto the SBA-15 support containing a bidentate N-O Schiff-base ligand was prepared and it was applied in the synthesis of quinoxaline, pyrazine and pyrido pyrazine heterocycles. The nanocatalyst was characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), infrared spectroscopy and nitrogen adsorption/desorption isotherm. The results from X-ray diffraction and transmission electron microscopy show that the textile properties of SBA-15 are preserved after grafting of manganese (II) complex. A variety of aforementioned heterocycles were synthesized easily and with good yields under green conditions in aqueous medium via ring condensation of 1,2-diamines and 1,2-diketones in the presence of  catalytic amounts of catalyst.
Keywords
Heterogeneous catalyst
Mn(II) complex
SBA-15
Quinoxaline
Pyridopyrazine
Water

Subjects

 [1] سلمه رسولی زاده، ملک طاهر مقصودلو، قاسم مرندی، سنتز مشتق‌های تری فنیل ایمیدازول با استفاده از پکتین به عنوان کاتالیست سبز، نشریه شیمی و مهندسی شیمی ایران، 38: 137-143 (1398).
[2] مهدی کلهر، سیما سمیعی، سید احمد میرشکرایی، سنتز و شناسایی نانو مزوپور منگنز دی اکسید/زئولیت و کاربرد آن به‌عنوان یک نانو کاتالیزگر مؤثر در سنتز اتیل بنزایمیدازولیل آمینوتیو استات­ها از طریق یک واکنش سه‌جزیی در شرایط سبز، نشریه شیمی و مهندسی شیمی ایران، 41(1): 27 تا 37 (1401).
[3] Maikhuri V.K.; Prasad A.K.; Jha A.; Srivastava S., Recent Advances in the Transition Metal Catalyzed Synthesis of Quinoxalines: A Review. New Journal of Chemistry. (2021).
[4] Kalhor M.; Seyedzade Z., Ni@ Zeolite-Y Nano-Porous: Preparation and Application as a High Efficient Catalyst for Facile Synthesis of Quinoxaline, Pyridopyrazine, and Indoloquinoxaline Derivatives. Iranian Journal of Chemistry Chemical Engineering, 38: 27-41 (2019).
[5] Slowing II.; Vivero-Escoto J.L.; Trewyn B.G.; Lin VS-Y., Mesoporous Silica Nanoparticles: Structural Design and Applications. Journal of Materials Chemistry, 20:7924-7937 (2010).
 [6] Kruk M.; Jaroniec M.; Ko C.H.; Ryoo R., Characterization of the Porous Structure of SBA-15. Chemistry of materials, 12: 1961-1968 (2000).
[7] Huo Q.; Margolese D.I.; Stucky G.D., Surfactant Control of Phases in the Synthesis of Mesoporous Silica-based Materials. Chemistry of Materials 8: 1147-1160 (1996).
[8] Ziarani G.M.; Roshankar S.; Mohajer F.; Badiei A., The Synthesis and Application of Functionalized Mesoporous Silica SBA-15 as Heterogeneous Catalyst in Organic Synthesis. Current Organic Chemistry. 25: 361-87 (2021).
[9] علی بدیعی، بهمن حسن زاده، رضا رحمانیان، سنتز سیلیکای نانو متخلخل (SBA-15) عامل دار شده با لیگاند آلی شامل گروه های کربوکسیلیک اسید و به کارگیری آن در حذف آلاینده صنایع آبزی پروری، نشریه پژوهش­ های کاربردی در شیمی (JARC )، 3: 15-22 (1393).
[10] Chisem I.C.; Rafelt J.; Chisem J.; Clark J.H.; Macquarrie D.; Shieh M.T.; et al, Catalytic Oxidation of Alkyl Aromatics Using a Novel Silica Supported Schiff base Complex. Chemical Communication. 18: 1949-1950 (1998).
[11] Pereira J.A.; Pessoa A.M.; Cordeiro M.N.D.; Fernandes R.; Prudêncio C.; Noronha J.P.; et al, Quinoxaline, Its Derivatives and Applications: A State of the Art review. European Journal of Medicinal Chemistry. 97: 664-672 (2015).
[12] Bardajee G.R.; Malakooti R.; Jami F.; Parsaei Z.; Atashin H., Covalent Anchoring of Copper-Schiff base Complex into SBA-15 as a Heterogeneous Catalyst for the Synthesis of Pyridopyrazine and Quinoxaline Derivatives. Catalysis Communications. 27: 49-53 (2012).
[13] Malakooti R.; Bardajee G.R.; Mahmoudi H.; Kakavand N., Zirconium Schiff-base Complex Modified Mesoporous Silica as an Efficient Catalyst for the Synthesis of Nitrogen Containing Pyrazine based Heterocycles. Catalysis letters. 143: 853-861 (2013).
 [14] Appel R., Imin-Sauerstoff-Austauschreaktione Zwischen Bis (Iminophosphoranen) Und Diketoneniketone. PChemBer. 108: 623 (1975).
[15] JCPDS Powder Diffraction File, International Center for Diffraction Data, PA: Swarthmore. (2000).
[16] Zheng Q.; Grossardt J.; Almkhelfe H.; Xu J.; Grady B.P.; Douglas J.T.; et al, Study of Mesoporous Catalysts for Conversion of 2, 3-Butanediol to Butenes. Journal of catalysis. 354: 182-196 (2017).