Cover Image

Green and efficient method for the synthesis of 1,5-benzodiazipines using phosphate fertilizers as catalysts under free solvent

Sibous Sibous, Touriya Ghailane, Serrar Houda, Rachida Ghailane, Said Boukhris, Abdelaziz Souizi

Abstract


Three-component reaction in one pot transformation of aldehydes, ethylacetoacetate and o-phenylenediamine was employed for the synthesis, under solvent-free, of 1,5-benzodiazepine derivatives using  fertilizers mono-ammonium  phosphate (MAP), di-ammonium Phosphate (DAP) and triple super phosphate (TSP) as safe, clean, and recyclable catalysts. The synthesis method seems to be operationally simple and provides access to a variety of 1,5-benzodiazepines with excellent yields in a short reaction time. 


Full Text:

PDF

References


- H. Schutz, Benzodiazepines, Publisher: Springer-Verlag, Berlin, Heidelberg, New York, 1982, PP. 439.

- J.K. Landquist, A.R. Katritzky, C.W. Rees, Comprehensive heterocyclic chemistry (Eds), Pergamon, Oxford, 1984, 1, 166-170.

- H. Nakano, T. Inoue, N. Kawasaki, H. Miyataka, H. Matsumoto, T. Taguchi, N. Inagaki, H. Nagai, T. Satoh, Synthesis and biological activities of novel antiallergic agents with 5-lipoxygenase inhibiting action, Bioorg. Med. Chem. 2000, 8, 373-380.

- L.O. Rundall, B. Kiappel, in: S. Garattini, E. Mussini, L.O. Randall (Eds.), Benzodiazepines, Raven Press, New York, 1973, 27.

- A.H. Jadhav, H. KimSolvent free synthesis of 1, 5-benzodiazepine derivatives over the heterogeneous silver salt of silicotungstic acid under ambient conditions. RSC Adv, 2013, 3, 5131-5140.

- X. Pan, Z. Zou, W. Zhang, Ga(OTf)3-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines. Tetrahedron Lett.2008, 49, 5302-5308.

- M.C. Aversa, A. Ferlazzo, P. Giannetto, F.H. Kohnke, A convenient synthesis of novel [1, 2, 4] triazolo [4, 3-a][1, 5] benzodiazepine derivatives, Synthesis, 1986, 1986, 230-231.

- W.K. Huang, C.W. Cheng, S.M. Chang, Y.P. Lee, E.W.G. Diau, Synthesis and electron-transfer properties of benzimidazole-functionalized ruthenium complexes for highly efficient dye-sensitized solar cells, Chem. Commun. 2010, 46, 8992-8994.

- K. S. Atwal, J. L. Bergey, A. Hedberg, S. Moreland, Synthesis and biological activity of novel calcium channel blockers: 2, 5-dihydro-4-methyl-2-phenyl-1, 5-benzo-thiazepine-3-carboxylic acid esters and 2,5-dihydro-4-methyl-2-phenyl-1, 5-benzo-diazepine-3-carboxylic acid esters, J. Med. Chem. 1987, 30, 635-640.

- M. D. Braccio, G. Grossi, G. Roma, L. Vargiu, M. Mura, M. E. Marongiu, 1, 5-Benzo-diazepines. Part XII. Synthesis and biological evaluation of tricyclic and tetracyclic 1, 5-benzodiazepine derivatives as nevirapine analogues, Eur. J.Med. Chem. 2001, 36, 935-949.

- M. Abdollahi-Alibeik, I. Mohammadpoor-Baltork, Z. Zaghaghi, B. Yousefi, Efficient synthesis of 1, 5-benzodiazepines catalyzed by silica supported 12-tungstophosphoric acid, Catal. Commun. 2008, 9, 2496-2502.

- Ç. Radatz, R. Silva, G. Perin, E. Lenardao, R. Jacob, D. Alves, Catalyst-free synthesis of benzodiazepines and benzimidazoles using glycerol as recyclable solvent. Tetrahedron Lett. 2011, 52, 4132-4136.

- D. P. Clifford, D. Jackson, R. V. Edwards, P. Jeffrey, Herbicidal and pesticidal properties of some 1, 5‐benzodiazepines, 1, 3, 5‐benzotriazepines and 3, 1, 5‐benzothia-diazepines, Pestic. Sci. 1976, 7, 453-458.

- 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, Science. 1990, 250, 1411-1413.

- M. Curini, F. Epifano, Ytterbium triflate promoted synthesis of 1,5-benzodiazepine derivatives. Tetrahedron Lett. 2001, 42, 3193-3195.

- M. Kodomari, T. Noguchi, Solvent‐free synthesis of 1, 5‐benzothiazepines and benzodiazepines on inorganic supports, Synth. Commun. 2004, 34, 1783-1790.

- C.A. Cortes, A. L. Valencia, New derivatives of dibenzo [b, e][1, 4] diazepin‐1‐ones by an efficient synthesis and spectroscopy, J. Heterocycl. Chem. 2007, 44, 183-184.

- D. McGowan, O. Nyanguile, M. D. Cummings, S. Vendeville, K. Vandyck, W. Van den Broeck, J. F. Bonfanti, 1, 5-Benzodiazepine inhibitors of HCV NS5B polymerase, Bioorg. Med. Chem. Lett. 2009, 19, 2492-2496.

- A. V. Vijayasankar, S. Deepa, B. R. Venugopal, N. Nagaraju, Amorphous mesoporous iron alumino-phosphate catalyst for the synthesis of 1, 5-benzodiazepines, Chin.J.Catal. 2010, 31, 1321-1327.

- S. L. Wang, C. Cheng, F.Y. Wu, B. Jiang, F. Shi, S. J. Tu, G. Li, Microwave-assisted multi-component reaction in water leading to highly regioselective formation of benzo [f] azulen-1-ones, Tetrahedron. 2011, 67, 4485-4493.

- L. D. Fader, R. Bethell, P. Bonneau, M. Bös, Y. Bousquet, M. G. Cordingley, N. Goudreau, Discovery of a 1, 5-dihydrobenzo [b][1, 4] diazepine-2, 4-dione series of inhibitors of HIV-1 capsid assembly, Bioorg. Med. Chem. Lett. 2011, 22, 398-404.

- A. Maleki, Fe3O4/SiO2 nanoparticles: an efficient and magnetically recoverable nanocatalyst for the one-pot multicomponent synthesis of diazepines. Tetrahedron. 2012, 68, 7827-7833.

- I. E. Tolpygin, N. V. Mikhailenko, A. A. Bumber, E. N. Shepelenko, U. V. Revinsky, A. D. Dubonosov, V. I. Minkin, 11-R-dibenzo [b, e][1, 4] diazepin-1-ones, the chemosensors for transition metal cations. Russ. J. Gen. Chem. 2012, 82, 1141-1147.

- B. Jiang, Q. Y. Li, H. Zhang, S. J. Tu, S. Pindi, G. Li, Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo [b, e][1, 4] diazepin-1-ones, Org. Lett. 2012, 14, 700-703.

- J. Schimer, P. Cígler, J. Veselý, K. GrantzŠašková, M. Lepsik, J. Brynda, H. G. Kraeusslich, Structure-Aided design of novel inhibitors of HIV protease based on a benzodiazepine scaffold, J. Med. Chem. 2012, 55, 10130-10135.

- M. Lal, R. S. Basha, S. Sarkar, A. T. Khan, 2, 6-Pyridinedicarboxylic acid as organocatalyst for the synthesis of 1, 5-benzodiazepines through one-pot reaction. Tetrahedron Lett. 2013, 54, 4264-4272.

- M. A. Chari, K. Syamasundar, Polymer (PVP) supported ferric chloride: an efficient and recyclable heterogeneous catalyst for high yield synthesis of 1, 5-benzodiazepine derivatives under solvent free conditions and microwave irradiation, Catal. Commun. 2005, 6, 67-70.

- A. Hegedüs, Z. Hell, A. Potor, A simple environmentally-friendly method for the selective synthesis of 1, 5-benzodiazepine derivatives using zeolite catalyst, Catal. Lett. 2005, 105, 229-232.

- M. Muñoz, G. Sathicq, G. Romanelli, S. Hernández, C. I. Cabello, I. L. Botto, M. Capron, Porous modified bentonite as efficient and selective catalyst in the synthesis of 1, 5-benzodiazepines, J. Porous Mater. 2013, 20, 65-73.

- J. S. Yadav, B. S. Reddy, S. Praveenkumar, K. Nagaiah, N. Lingaiah, P. S. Saiprasad, Ag3PW12O40: a novel and recyclable heteropoly acid for the synthesis of 1, 5-benzo-diazepines under solvent-free conditions, Synthesis. 2004, 2004, 901-904.

- M. M. Heravi, S. Sadjadi, H. A. Oskooie, R. Hekmatshoar, F. F. Bamoharram, An Efficient Synthesis of 3H‐1, 5‐Benzodiazepine Derivatives Catalyzed by Heteropolyacids as a Heterogeneous Recyclable Catalyst, J. Chin. Chem. Soc. 2008, 55, 842-845.

- T. D. Le, K. D. Nguyen, V. T. Nguyen, T. Truong, N. T. Phan, 1, 5-Benzodiazepine synthesis via cyclocondensation of 1, 2-diamines with ketones using iron-based metal-organic framework MOF-235 as an efficient heterogeneous catalyst. ‎J. Catal., 2016, 333, 94-101.

- N. K. Terrett, Combinatorial Chemistry, Oxford University Press, New York, NY, 1998.

- J. Zhu, H. Bienayme, Multicomponent Reactions (Ed.), Wiley-VCH, Weinheim, Germany, 2005.

- L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions inOrganic Synthesis, Wiley-VCH, Weinheim, 2006.

- K. Murai, R. Nakatani, Y. Kita, H. Fujioka, One-pot three-component reaction providing 1,5-benzodiazepine derivatives, Tetrahedron, 2008, 64, 11034-11040.

- L. Banfi, A. Basso, L. Giardini, R. Riva, V. Rocca, G. Guanti, Tandem Ugi MCR/Mitsunobu Cyclization as a Short, Protecting‐Group‐Free Route to Benzoxazinones with Four Diversity Points, Eur. J.Org. Chem., 2011, 2011, 100-109.

- G. K. Verma, K. Raghuvanshi, R. K. Verma, P. Dwivedi, M. S. Singh, An efficient one-pot solvent-free synthesis and photophysical properties of 9-aryl/alkyl-octahydroxanthene-1, 8-diones. Tetrahedron, 2011, 67, 3698-3704.

- M. Ghandi, T. Momeni, M. T. Nazeri, N. Zarezadeh, M. Kubicki, A one-pot three-component reaction providing tricyclic 1, 4-benzoxazepine derivatives, Tetrahedron Lett., 2013, 54, 2983-2985.

- Z. Karimi-Jaberi, M. Barekat M, One-pot synthesis of tri-and tetra-substituted imidazoles using sodium dihydrogen phosphate under solvent-free conditions. Chin Chem Lett., 2010, 21, 1183-1186.

- Y. Han, Y. Sun, J. Sun, CG. Yan, Efficient synthesis of pentasubstituted pyrroles via one-pot reactions of arylamines, acetylenedicarboxylates, and 3-phenacylidene-oxindoles. Tetrahedron, 2012, 68, 8256-8260.

- M. Li, H. Cao, Y. Wang, X-L. Lv, LR.Wen, One-pot multicomponent cascade reaction of N, S-ketene acetal: Solvent-free synthesis of imidazo [1,2-a] thiochromeno [3,2-e] pyridines. Org. Lett., 2012, 14, 3470-3473.

- F. Shirini, SS. Beigbaghlou, SV. Atghia, SAR. Mousazadeh, Multi-component one-pot synthesis of unsymmetrical dihydro-5H-indeno [1, 2-b] quinolines as new pH indicators. Dyes Pigm., 2013, 97, 19-25.

- K. Murai, R.Nakatani, Y. Kita, H. Fujioka, One-pot three-component reaction providing 1, 5-benzodiazepine derivatives. Tetrahedron, 2008, 45, 11034-11040.

- I. Bahammou, A. Esaady, S. Boukhris, R. Ghailane, N. Habbadi, A. Hassikou, A. Souizi, Direct use of mineral fertilizers MAP, DAP, and TSP as heterogeneous catalysts in organic reactions, Mediterr. J. Chem., 2016, 5, 615-623.

- S. Sarkar, J. K. R. Deka, J. P. Hazra, A. T. Khan, Bromodimethylsulfonium Bromide (BDMS)-Catalyzed Synthesis of 1, 5-Benzo-diazepines Using a Multi-Component Reaction Strategy. Synlett., 2013, 24, 2601-2605.

- Xiao-Qing Li, Lan-Zhi Wang, ‎ Highly efficient one-pot, three-component synthesis of 1, 5-benzodiazepine derivatives. Chin. Chem. Lett. 2014, 25, 327-332.




DOI: http://dx.doi.org/10.13171/mjc61/01701181035/souizi

Refbacks

  • There are currently no refbacks.


Copyright (c) 2017 Mediterranean Journal of Chemistry