Synthesis of 2, 4 disubstituted 1, 5 benzodiazepines promoted by efficient Silica-Alumina Catalyst

Document Type : Research Article

Authors

1 Mahant Jamnadas Maharaj Arts, Commerce and Science college, Karanjali, Nashik, India

2 Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431004, India

Abstract

An efficient and environment friendly valuable synthon of 1, 5 benzodiazepine derivatives were synthesized having unique physical and medicinal properties. This reaction is performed by mesoporous binary mixed metal oxide SiO2-Al2O3 which is synthesized by hydrothermal method at high temperature. This mesoporous material is investigated by XRD, SEM, EDS, TEM, TPD and BET surface area. Present method offers several remarkable advantages such as non-toxic, noncorrosive and easy work-up procedure for the purification of product with non-chromatographic method, ecofriendly reaction condition.

Graphical Abstract

Synthesis of 2, 4 disubstituted 1, 5 benzodiazepines promoted by efficient Silica-Alumina Catalyst

Keywords


[1] A. Pareek, N. Kumar, A. Agarwal, P. Sharma and D. Kishore, 1, 5 Benzodiazepines: Overview of Properties and Synthetic Aspects. Res. J. Chem. Sci., 3(7) (2013) 90-103.
[2] M. S. Saini, A. Kumar, J. Dwivedi and R. Singh, A review: biological significances of heterocyclic compounds. Int. J. Pharma. Sci. Res., 4(3) (2013) 66.
[3] A. Thakkar, A Study on Biological Importance of Nitrogenous Based HeterocyclicCompounds. Inter. J. Theor. Appl. Sci., 8(1) (2016) 53-54.
[4] A. S. Suvarna, A Review on Synthetic Hetrocyclic Compounds in Agriculturaland other Applications. Int. J. Pharm. Tech. Res., 8(8) (2015) 170-179.
[5] A. Lauria, R. Delisi, F. Mingoia, A. Terenzi, A. Martorana, G. Barone, A. M. Almerico, 1,2,3‐Triazole in Heterocyclic Compounds, Endowed with Biological Activity, through 1,3‐Dipolar Cycloadditions. Eur. J. Org. Chem., (2014) 3289-3306.
[6] N. Adki, G. Ravi, Naseem, S. Sharath Kumar, G. R. Nageswara, Synthesis of new biologically active compounds containing linked thiazolyl-thiazolidinone heterocycles. Org. Commun., 5(4) (2012) 160-170.
[7] S. S. Kale, R. R. Pawar, A. S. Kale, Imidazole, Its Derivatives & Their Importance: A Review. Int. J. Curr. Advanced Res., 5(5) (2016) 906-911.
[8] M. Al-Ghorbani, B. Begum, A. Zabiulla, S. V. Mamatha, S. A. Khanum, Piperazine and morpholine: Synthetic preview and pharmaceutical applications. J. Chem. Pharma. Res., 7(5) (2015) 281-301.
[9] R. Mishra, K. K. Jha, S. Kumar, I. Tomer, Synthesis, properties and biological activity of thiophene: A review. Der Pharm. Chemica., 3(4) (2011) 38-54.
[10] J. Młochowski, K. Kloc, R. Lisiak, P. Potaczek, H. Wojtowicz, Developments in the chemistry of selenaheterocyclic compounds of practical importance in synthesis and medicinal biology. A.R.K.I.V.O.C., 6 (2007) 14-46.
[11] M. Baumann, I. R. Baxendale, An overview of the synthetic routes to the bestselling drugs containing 6-membered heterocycles. Beilstein J. Org. Chem., 9, (2013) 2265-2319.
[12] Michael J. Kukla, Henry J. Breslin, Rudi Pauwels, Cynthia L. Fedde, Milton Miranda, Malcolm K. Scott, Ronald G. Sherrill, Alfons Raeymaekers, Jozef Van Gelder, Koen Andries, Marsel A.C. Jannsen, Erik de Clerq and Paul A.J. Jannsen. Berslin, J. Med. Chem, 34 (1991) 746-751.
[13] C. Page, C. Michael, M. Sutter, M. Walker, B. B. Hoffman, Integrated Pharma., (2ndEd.). C.V. Mosby(2002) ISBN 978-0-7234-3221-0.
[14] A. R. Katrizky, R. Abonia, B. Yang, M. Qi, B, Insuasty, Synthesis.,(1998) 1487.
[15] R. I. Shader, Benzodiazepines in clinical medicine: discussion. Br. J. clin. Pharmac., 11 (1981) 55-59.
[16] D. S. Baldwin, K. Aitchison, A. Bateson, H. V. Curran, S. Davies, B. Leonard, D. J. Nutt, D. N. Stephens, S. Wilson, Benzodiazepines: risks and benefits. A reconsideration . J. Psychopharma., 27(11) (2013) 967-971.
[17] D. P. Clifford, D. Jackson, R. V. Edwards, P . Jefferey. Herbicidal and pesticidal properties of some 1,5-benzodiazepines, 1,3,5-benzotriazepines and 3,1,5-benzothiadiazepines. Pestic. Sci., 7 (1976) 453-458.
[18] W. Werner, K. Wohlrabe, W. Gutsche, W. Jungstand, W. Roemer, Folida Haematol, 108 (1981) 637.
[19] D. A. Goff, R. N. Zuckermann, Solid-phase synthesis of defined 1,4-benzodiazepine-2,5-dione mixtures. J. Org. Chem., 60 (1995) 5744-5745.
[20] H. Schutz, Benzodiazepines; Springer: Heidelberg, Germany, (1982).
[21] L. O. Randall, B. Kamel, S. Garattini, E. Mussini, L. O. Randall, Eds.; Raven Press: New York, (1973) 27.
[22] C. M. Sandra, C. C. Eduardo, H. O. Simon, R. A. Teresa, N. C. Antonio, I. V. Lijanova, M. G. Marcos, Anticancer activity and anti-inflammatory studies of 5-aryl-1,4-benzodiazepine derivatives. Anti-Cancer Agents in Med. Chem., 12 (2012) 611-618.
[23] V. Shahnavaz, K. B. Farahnaz, Org. Chem. Ind. J., 12(4) (2016) 103.
[24] C. W. Kuo, C. C. Wang, V. Kavala, C. F. Yao, Efficient TCT-catalyzed Synthesis of 1,5-Benzodiazepine Derivatives under Mild Conditions. Molecules., 13 (2008) 2313-2325.
[25] P. Aastha, K. Navneet, A. Anshu, S. Pratima, K. Dharma, 1, 5 Benzodiazepines: Overview of Properties and Synthetic Aspects. Res. J. Chem. Sci., 3(7) (2013) 90-103.
[26] R. A. Stein, T. L. Strickland, A Review of the Neuropsychological Effects ofCommonly Used Prescription Medications. Archiv. Clinical Neuro., 13(3) (1998) 259-284.
[27] J. S. Yadav, B. V. S. Reddy, G. Satheesh, G. Srinivasulu, A. C. Kunwar, InCl3-Catalyzed stereoselective synthesis of 1,5-benzodiazepines. A.R.K.I.V.O.C., 3 (2005) 221-227.
[28] J. R. D. Baun, F. M. Pallos, D. R. Baker, U. S. Patent., 3 978, (1976) 227.
[29] S. S. Ilango, P. U. Ramya, S. Ponnuswamy, Synthesis and antimicrobial activity of novel 1,5-benzodiazepines. Indian J. Chem., 52B (2013) 136-140.
[30] M. Baumann, I. R. Baxendale, S. V. Ley, N. Nikbin, An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals. Beilstein J. Org. Chem., 7 (2011) 442-495.
[31] T. Clayton, M. M. Poe, S. Rallapalli, P. Biawat, M. M. Savit, J. K. Rowlett, G. Gallos, C. W. Emala, C. C. Kaczorowski, D. C. Stafford, L. A. Arnold, J. M. Cook, Int. J. Medicinal Chem., (2015) 54.
[32] V. Merluzzi, K. D. Hargrave, M. Labadia, K. Grozinger, M. Skoog, J. C. Wu, C. K. Shih, K. Eckner, S. Hattox, J. Adams, A. S. Rosenthal, R. Faanes, R. J. Eckner, R. A. Koup, J. L. Sullivan, Inhibition of HIV-1 replication by a nonnucleoside reverse transcriptase inhibitor, Sci.,250 (1990) 1411-1413.
[33] D. M. Braccio, G. Grossi, G. Romoa, L. Vargiu, M. Mura, M. E. Marongiu, 1,5-Benzodiazepines. Part XII. Synthesis and biological evaluation of tricyclic and tetracyclic 1,5-benzodiazepine derivatives as nevirapine analogues. Eur. J. Med.Chem., 36 (2001) 935-949.
[34] G. K. Nagaraja, V. P. Vaidya, K. S. Rai, K. M. Mahadevan, An Efficient Synthesis of 1,5-Thiadiazepines and 1,5-Benzodiazepines by Microwave-Assisted Heterocyclization, Phosphorus. Sulfur. Silicon. Relat. Elem., 181 (2006) 2797-2806.
[35] K. Nabih, A. Baouid, A. Hasnaoui, A. Kenz, Highly Regio‐ and Diastereoselective 1,3‐Dipolar Cycloaddition of Nitrile Oxides to 2,4‐Dimethyl‐3H‐1,5‐Benzodiazepines: Synthesis of Bis[1,2,4‐Oxadiazolo][1,5]Benzodiazepine Derivatives. Synth. Commun., 34 (2004) 3565-3572.
[36] C. W. Kuo, C. C. Wang, V. Kavala, C. F. Yao, Efficient TCT-catalyzed Synthesis of 1,5-Benzodiazepine Derivatives under Mild Conditions. Molecules.,13 (2008) 2313-2325.
[37] M. E. Welsch, S. A. Snyder, B. R. Stockwell, Privileged scaffolds for library design and drug discovery. Curr. Opin. Chem. Biol., 14(3) (2010) 347-361.
[38] K. A. M. El-Bayouki, Benzo[1,5]thiazepine: Synthesis, Reactions, Spectroscopy, and Applications. Org. Chem. Int., (2013) 1-71.
[39] L. Richter, C. D. Graaf, W. Sieghart, Z. Varagic, M. Morzinger, I. J. P. Esch, G. F. Ecker, M. Ernst, Diazepam-bound GABAA receptor models identify new benzodiazepine binding-site ligands. Nat. Chem. Biol., 8(5) (2012) 455-464.
[40] J.Y. Wang, X. F. Guo, D.X. Wang, Z.T. Huang, and M.X. Wang, A New Strategy for the Synthesis of 1,4-Benzodiazepine Derivatives Based on the Tandem N-Alkylation−Ring Opening−Cyclization Reactions of Methyl 1-Arylaziridine-2-carboxylates with N-[2-Bromomethyl(phenyl)]trifluoroacetamides. J. Org. Chem., 73(5), (2008) 1979–1982.
[41] X. Ma, X. Zhang, W. Qiu, W. Zhang, B. Wan, J. Evans and W. Zhang, One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions, Molecules., 24, (2019) 601.
[42] M. N. Timofeeva, E. A. Petrova, E. A. Mel’gunova, A. Gil, M. A. Vicente & V. N. Panchenko, Reaction Kinetics, Mechanisms and Catalysis, 127 (2019) 41–52.
[43] G. D. Yadav, A. R. Yadav, Selective Green Synthesis of 1,5-Benzodiazepine over Modified Heteropolyacid as Nanocatalyst: Kinetics and Mechanism. Ind. Eng. Chem. Res., (2013) 52, 50, 17812-17820.
[44] R. Jamatia, M. Saha and A. K. Pal, An efficient facile and one-pot synthesis of benzodiazepines and chemoselective 1,2-disubstituted benzimidazoles using a magnetically retrievable Fe3O4 nanocatalyst under solvent free conditions, RSC Adv, 4, (2014) 12826-12833.
[45] M. Esfandiari, A. K. Abbas, H. S. Alavi, J. S. Ghomi,, Synthesis of Benzodiazepines Promoted by CeO2/CuO@Nitrogen Graphene Quantum Dots@NH2 Nanocomposite, Polycyclic aromatic compounds., 40 (2020) 1-6.
[46] M. Muaoz, G. Pasquale, A. G. Sathicq, G. P. Romanelli, C. I. Cabello and D. Gazzoli, Volcanic ash as reusable catalyst in the green synthesis of 3H-1,5-benzodiazepines, Green Process Synth., 8 (2019) 600–610.
[47] S. Sarhandi, L. Zare Fekri, E. Vessally, Ultrasound Assisted Chromatography-Free Synthesis of Triazolo [1,2-a]Indazole-Triones in the Presence of 1,4-Diazabicyclo[2.2.2] Octanium Diacetate as an Environmentally Friendly Green Media, polycyclic aromatic compounds., (2019), 1-11, in press.
[48] B. M. Reddy, P. M. Sreekanth, An efficient synthesis of 1,5-benzodiazepine derivatives catalyzed by a solid superacid sulfated zirconia.Tetrahedron Lett., 44 (2003) 4447-4449.
[49] J. M. Yadav, D. Pathak, Synthesis and biological evaluation of some newer 1,5-benzodiazepine derivatives as potential anticonvulsant agents. Der Pharma. Sinica., 4(4) (2013) 81-90.
[50] S. A. Majid, W. A. Khanday, R. Tomar, Synthesis of 1,5-benzodiazepine and its derivatives by condensation reaction using H-MCM-22 as catalyst. J. Biomed. Biotechnol., (2012) 1-6.
[51] R. Varala, R. Enugala, S. R. Adapa, p-Nitrobenzoic Acid Promoted Synthesis of 1,5-Benzodiazepine Derivatives. J. Braz. Chem. Soc., 18(2) (2007) 291-296.
[52] Bilal A. Ganai, Kumar S, Charanjeet S. Andotra, Kamal K. Kapoor, SbCl3‐Al2O3–Catalyzed, Solvent‐Free, One‐Pot Synthesis of Benzo[b]1,4‐diazepines, Synth Commun. 36, (2006) 803.
[53] Sucheta K, Vital Rao B. Microwave induced solvent-free synthesis of substituted 1,5-benzodiazepine derivatives, Indian J Chem. 44B, (2005) 2152-2154.
[54] M. A. Alibeik, Z. Zaghaghi, I. M. Baltork, Alumina Supported 12‐Tungstophosphoric Acid as an Efficient and Reusable Catalyst for Synthesis of 1,5‐Benzodiazepines, J. Chinese Chem. Soc., 55, (2008) 1-4.
[55] A. Shaabani, A. Maleki, A Fast and Efficient Method for the Synthesis of 1,5-Benzodiazepine Derivatives Under Solvent-Free Conditions. Iran. J. Chem. Chem. Eng., 26, (2007) 93-97.
[56] A. K. Yadav, M. Kumar, T. Yadav, R. Jain, A novel one pot room temperature ionic liquid mediated synthesis of 1,5-benzodiazepine ribofuranosides. Indian J. Chem., 49B (2010) 461-468.
[57] M. S. Bhatia, P. B. Choudhari, K. B. Ingale, B. E. Zarekar, Synthesis, screening and QSAR studies of 2,4-disubstituted 1,5-benzodiazepine derivatives. Oriental J. Chem., 24(1) (2008) 147-152.
[58] R. Singh, N. Kumar, M. Yadav, D. Pathak, Microwave-Assisted, Solvent Free and Parallel Synthesis of Some Newer 2, 4-Disubstituted 1, 5- Benzodiazepines of Biological Interest. Int. J. Pharma. Sci. Drug Res., 5(3) (2013) 88-95.
[59] P. Narendiran, S. Guhanathan, Int. J. Frontiers Sci. Technol., 3(1) (2015).
[60] N. A. A. Jaber, A. S. A. Bougasim, M. M. S. Karah, Study of Michael addition on chalcones and or chalconeanalogues. J. Saudi Chem. Soc., 16 (2012) 45-53.
[61] L. Chen, T. V. W. Janssens, M. Skoglundh, H. Gronbeck, Interpretation of NH3‑TPD Profiles from Cu‑CHA Using First‑Principles Calculations. Topics in Catalysis., 62 (2019) 93-99.
[62] A.K. Saidfar, M. Alizadeh, S. Pirsa, Application of Nano-sized Poly (N-methyl pyrrole-pyrrole) Fiber to the Headspace Solid-Phase Microextraction of Volatile Organic Compounds from Yogurt. J. Chem. Lett.1., 1 (2020) 39-46.