Main Article Content
Abstract
A hexachlorocyclotriphosphazene (HCCP) catalyzed new method has been developed for the synthesis of 2,3-dihydro-1H-1,5-benzodiazepines by cyclocondensation of o-phenylenediamine with aromatic aldehydes or ketones in acetonitrile at room temperature. This protocol is developed as a clean and safe method utilizing environmentalfriendly and highly efficient catalyst.
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References
- (a) H. Schutz, Benzodiazepines, Springer: Heidelberg (1982); (b) J.K. Landquist, eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocylic Chemistry, vol. 1, pp. 166–170 (1984).
- O. Nyanguile, F. Pauwels, W. Van den Broeck, C.W. Boutton, L. Quirynen, T. Ivens, L. van der Helm, G. Vandercruyssen, W. Mostmans, F. Delouvroy, P. Dehertogh, M.D. Cummings, J.-F. Bonfanti, K.A. Simmen and P. Raboisson, 1,5-Benzodiazepines, A Novel Class of Hepatitis C Virus Polymerase Non-nucleoside Inhibitors, Antimicrob. Agents Chemother., 52, 4420 (2008); https://doi.org/10.1128/AAC.00669-08.
- A. Kamal, N. Shankaraiah, S. Prabhakar, C.R. Reddy, N. Markandeya, K.L. Reddy and V. Devaiah, Solid-Phase Synthesis of New Pyrrolo-benzodiazepine-Chalcone Conjugates: DNA-Binding Affinity and Anti-cancer Activity, Bioorg. Med. Chem. Lett., 18, 2434 (2008); https://doi.org/10.1016/j.bmcl.2008.02.047.
- Y. Larry, Privileged Structures in Drug Discovery: Medicinal Chemistry and Synthesis, Wiley, pp. 16-28 (2018).
- R.K. Singh, S. Sharma, A. Kaur, M. Saini and S. Kumar, Recent Advances in the Synthetic Approaches and Current Pharmacological Applications of 1,4-Dihydropyridines, Iran. J. Catal., 6, 1 (2016).
- S. Mohd, M. Mobin, A. Ali, S. Zaman and A.H. Naqvi, Graphene-Meso-porous Anatase TiO2 Nanocomposite: A Highly Efficient and Recycl-able Heterogeneous Catalyst for One-Pot Multicomponent Synthesis of Benzodiazepine Derivatives, Appl. Organomet. Chem., 32, e3961 (2018); https://doi.org/10.1002/aoc.3961.
- T.D. Le, K.D. Nguyen, V.T. Nguyen, T.T. Nam and T.S. 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., 333, 94 (2016); https://doi.org/10.1016/j.jcat.2015.10.026.
- H. Naeimi and H. Foroughi, ZnS Nanoparticles as an Efficient Recycl-able Heterogeneous Catalyst for One-Pot Synthesis of 4-Substituted-1,5-Benzodiazepines, New J. Chem., 39, 1228 (2015); https://doi.org/10.1039/C4NJ01893A.
- K.V.V. Satyanarayana, M.R. Chandra, P.A. Ramaiah, Y.L.N. Murthy, Y.S. Gil and S.V.N. Pammi, Green and Reusable Nanocatalyst for the Synthesis of 1,5-Benzodiazepines and Its Derivatives under Solvent-Free Conditions, Chem. Lett., 44, 1589 (2015); https://doi.org/10.1246/cl.150663.
- L. Yin and L. Wang, Chemo-/Regio-Selective Synthesis of 2-Aryl-3-acetyl-2,4-dihydro-1H-5H-1,5-benzodiazepines using Lewis acid, CeCl3·7H2O, Tetrahedron Lett., 57, 5935 (2016); https://doi.org/10.1016/j.tetlet.2016.11.089.
- R.K. Singh, M. Saini and S. Kumar, Rapid and Efficient Synthesis of 1,5-Benzodiazepines Promoted by Stannic Oxide Nanoparticles Under Solvent-Free Conditions, Indian J. Heterocycl. Chem., 25, 151 (2015).
- B. Hu, X. Zhang, L. Sheng, M. Guo, Z. Shen, X. Hu, N. Sun and W. Mo, Hexachlorocyclotriphosphazene (HCCP)-Mediated Direct Formation of Thioethers and Ethers from Quinazolin-4(3H)-ones, Molecules, 18, 5580 (2013); https://doi.org/10.3390/molecules18055580.
- Z.L. Shen, X.F. He, J.L. Dai, W.M. Mo, B.X. Hu, N. Sun and X.Q. Hu, An Efficient HCCP-Mediated Direct Amination of Quinazolin-4(3H)-ones, Tetrahedron, 67, 1665 (2011); https://doi.org/10.1016/j.tet.2010.12.067.
- R. Duvedi and R.K. Singh, Environment Friendly, Efficient Chloroacetic Acid Promoted Synthesis of 1-Amidoalkyl-2-naphthols under Neat Condition, Asian J. Chem., 24, 5665 (2012).
- S. Sharma, D.N. Prasad and R.K. Singh, One pot Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines under Solvent-Free Conditions using Anhydrous Stannous Chloride as Catalyst, J. Chem. Pharm. Res., 3, 382 (2011).
- A. Sandhar, D.N. Prasad and R.K. Singh, Salicylic Acid Catalyzed Synthesis of 2,3-dihydro-1H-1,5-benzodiazepines under Solvent-Free Condition, Indian J. Heterocyl. Chem., 21, 369 (2012).
- A. Sandhar, D.N. Prasad, A. Kapoor and R.K. Singh, Efficient p-Amino Benzoic Acid Catalyzed Eco-friendly Synthesis of 1,5-benzodiazepines among Various Amino Acids under Solvent Free Conditions, Curr. Res. Chem., 4, 68 (2012); https://doi.org/10.3923/crc.2012.68.75.
- S. Malik, S. Sharma and R.K. Singh, Microwave Assisted Synthesis of 1-Amidoalkyl-2-naphthols Catalyzed by Anhydrous Zinc Chloride, Asian J. Chem., 24, 5669 (2012).
- P. Kaur, H. Sharma, R. Rana, D.N. Prasad and R.K. Singh, Comparative Study of Various Green Chemistry Approaches for the Efficient Synthesis of 1,4-Dihydropyridines, Asian J. Chem., 24, 5649 (2012).
- A. Sandhar and R.K. Singh, A Simple, Efficient and Eco-Friendly Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines Mediated by Tannic Acid under Solvent-Free Condition, Asian J. Chem., 24, 5643 (2012).
- A. Sandhar and R.K. Singh, Rapid and Efficient Synthesis of 2,3-Dihydro-1H-1,5-Benzodiazepines Catalyzed by Chloroacetic Acid Screened among Various Aliphatic Acids under Solvent Free Conditions, Chem. Sci. Trans., 2, 176 (2012); https://doi.org/10.7598/cst2013.315.
- P. Kaur and R.K. Singh, Investigation of Various Green Chemistry Approaches for the Efficient Synthesis of Dialkyl-1,4-dihydro-4-(substituted phenyl)-2,6-dimethylpyridine-3,5-dicarboxylate, Chem. Sci. Trans., 2(S1), S295 (2013); https://doi.org/10.7598/cst2013.443.
- Y. Zhao, S. Sharma, M. Huang, A. Sandhar, R.K. Singh and Y. Ma, Investigation of Various Organocatalysts for Improved and Efficient One Pot Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines under Solvent-Free Condition, Asian J. Chem., 26, 5116 (2014); https://doi.org/10.14233/ajchem.2014.16440.
- T. Li, X. Zhai, D. Singh, R.K. Singh and X. Xu, Multicomponent One-pot Green Synthesis of 1-Amidoalkyl-2-naphthols Promoted by p-Nitrobenzoic Acid under Solvent-Free Condition, Asian J. Chem., 26, 5207 (2014); https://doi.org/10.14233/ajchem.2014.16707.
- R.K. Singh, B. Singh, R. Duvedi and S. Kumar, Sulfanilic Acid: A Versatile and Efficient Catalyst among Various Organoacids Screened for the Synthesis of 1-Amidoalkyl-2-Naphthols under Solvent-Free Condition, Res. Chem. Intermed., 41, 4083 (2015); https://doi.org/10.1007/s11164-013-1513-5.
- R.K. Singh, R. Bala and S. Kumar, Microwave Assisted Facile Synthesis of 1-Amidoalkyl-2-naphthols Catalyzed by Stannous Oxide Nano-particles, J. Indian Chem. Soc., 92, 1161 (2015).
- Y. Zhao, X. Yu, M. Saini, Y. Ma and R.K. Singh, Highly Efficient Zinc Oxide Nanoparticles Catalyzed Green Synthesis of 1,5-Benzodiazepines under Solvent-Free Path, Asian J. Chem., 26, 8539 (2014); https://doi.org/10.14233/ajchem.2014.18319.
- R.K. Singh, R. Bala and S. Kumar, An Efficient Synthesis of 1-Amidoalkyl-2-Naphthols Catalyzed by Zinc Oxide Nanoparticles Under Solvent-Free Conditions, Indian J. Chem., 55B, 381 (2016).
- R.K. Singh and R. Duvedi, Environment-Friendly Green Chemistry Approaches for an Efficient Synthesis of 1-Amidoalkyl-2-Naphthols Catalyzed by Tannic Acid, Arab. J. Chem., 11, 91 (2018); https://doi.org/10.1016/j.arabjc.2014.08.022.
- S. Chaudhary, S. Sharda, D.N. Prasad, S. Kumar and R.K. Singh, Synthetic Methodologies and Pharmacological Significance of 2-Aminobenzophenones as Versatile Building Block, Asian J. Org. Med. Chem, 3, 107 (2018); https://doi.org/10.14233/ajomc.2018.AJOMC-P136.
References
(a) H. Schutz, Benzodiazepines, Springer: Heidelberg (1982); (b) J.K. Landquist, eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocylic Chemistry, vol. 1, pp. 166–170 (1984).
O. Nyanguile, F. Pauwels, W. Van den Broeck, C.W. Boutton, L. Quirynen, T. Ivens, L. van der Helm, G. Vandercruyssen, W. Mostmans, F. Delouvroy, P. Dehertogh, M.D. Cummings, J.-F. Bonfanti, K.A. Simmen and P. Raboisson, 1,5-Benzodiazepines, A Novel Class of Hepatitis C Virus Polymerase Non-nucleoside Inhibitors, Antimicrob. Agents Chemother., 52, 4420 (2008); https://doi.org/10.1128/AAC.00669-08.
A. Kamal, N. Shankaraiah, S. Prabhakar, C.R. Reddy, N. Markandeya, K.L. Reddy and V. Devaiah, Solid-Phase Synthesis of New Pyrrolo-benzodiazepine-Chalcone Conjugates: DNA-Binding Affinity and Anti-cancer Activity, Bioorg. Med. Chem. Lett., 18, 2434 (2008); https://doi.org/10.1016/j.bmcl.2008.02.047.
Y. Larry, Privileged Structures in Drug Discovery: Medicinal Chemistry and Synthesis, Wiley, pp. 16-28 (2018).
R.K. Singh, S. Sharma, A. Kaur, M. Saini and S. Kumar, Recent Advances in the Synthetic Approaches and Current Pharmacological Applications of 1,4-Dihydropyridines, Iran. J. Catal., 6, 1 (2016).
S. Mohd, M. Mobin, A. Ali, S. Zaman and A.H. Naqvi, Graphene-Meso-porous Anatase TiO2 Nanocomposite: A Highly Efficient and Recycl-able Heterogeneous Catalyst for One-Pot Multicomponent Synthesis of Benzodiazepine Derivatives, Appl. Organomet. Chem., 32, e3961 (2018); https://doi.org/10.1002/aoc.3961.
T.D. Le, K.D. Nguyen, V.T. Nguyen, T.T. Nam and T.S. 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., 333, 94 (2016); https://doi.org/10.1016/j.jcat.2015.10.026.
H. Naeimi and H. Foroughi, ZnS Nanoparticles as an Efficient Recycl-able Heterogeneous Catalyst for One-Pot Synthesis of 4-Substituted-1,5-Benzodiazepines, New J. Chem., 39, 1228 (2015); https://doi.org/10.1039/C4NJ01893A.
K.V.V. Satyanarayana, M.R. Chandra, P.A. Ramaiah, Y.L.N. Murthy, Y.S. Gil and S.V.N. Pammi, Green and Reusable Nanocatalyst for the Synthesis of 1,5-Benzodiazepines and Its Derivatives under Solvent-Free Conditions, Chem. Lett., 44, 1589 (2015); https://doi.org/10.1246/cl.150663.
L. Yin and L. Wang, Chemo-/Regio-Selective Synthesis of 2-Aryl-3-acetyl-2,4-dihydro-1H-5H-1,5-benzodiazepines using Lewis acid, CeCl3·7H2O, Tetrahedron Lett., 57, 5935 (2016); https://doi.org/10.1016/j.tetlet.2016.11.089.
R.K. Singh, M. Saini and S. Kumar, Rapid and Efficient Synthesis of 1,5-Benzodiazepines Promoted by Stannic Oxide Nanoparticles Under Solvent-Free Conditions, Indian J. Heterocycl. Chem., 25, 151 (2015).
B. Hu, X. Zhang, L. Sheng, M. Guo, Z. Shen, X. Hu, N. Sun and W. Mo, Hexachlorocyclotriphosphazene (HCCP)-Mediated Direct Formation of Thioethers and Ethers from Quinazolin-4(3H)-ones, Molecules, 18, 5580 (2013); https://doi.org/10.3390/molecules18055580.
Z.L. Shen, X.F. He, J.L. Dai, W.M. Mo, B.X. Hu, N. Sun and X.Q. Hu, An Efficient HCCP-Mediated Direct Amination of Quinazolin-4(3H)-ones, Tetrahedron, 67, 1665 (2011); https://doi.org/10.1016/j.tet.2010.12.067.
R. Duvedi and R.K. Singh, Environment Friendly, Efficient Chloroacetic Acid Promoted Synthesis of 1-Amidoalkyl-2-naphthols under Neat Condition, Asian J. Chem., 24, 5665 (2012).
S. Sharma, D.N. Prasad and R.K. Singh, One pot Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines under Solvent-Free Conditions using Anhydrous Stannous Chloride as Catalyst, J. Chem. Pharm. Res., 3, 382 (2011).
A. Sandhar, D.N. Prasad and R.K. Singh, Salicylic Acid Catalyzed Synthesis of 2,3-dihydro-1H-1,5-benzodiazepines under Solvent-Free Condition, Indian J. Heterocyl. Chem., 21, 369 (2012).
A. Sandhar, D.N. Prasad, A. Kapoor and R.K. Singh, Efficient p-Amino Benzoic Acid Catalyzed Eco-friendly Synthesis of 1,5-benzodiazepines among Various Amino Acids under Solvent Free Conditions, Curr. Res. Chem., 4, 68 (2012); https://doi.org/10.3923/crc.2012.68.75.
S. Malik, S. Sharma and R.K. Singh, Microwave Assisted Synthesis of 1-Amidoalkyl-2-naphthols Catalyzed by Anhydrous Zinc Chloride, Asian J. Chem., 24, 5669 (2012).
P. Kaur, H. Sharma, R. Rana, D.N. Prasad and R.K. Singh, Comparative Study of Various Green Chemistry Approaches for the Efficient Synthesis of 1,4-Dihydropyridines, Asian J. Chem., 24, 5649 (2012).
A. Sandhar and R.K. Singh, A Simple, Efficient and Eco-Friendly Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines Mediated by Tannic Acid under Solvent-Free Condition, Asian J. Chem., 24, 5643 (2012).
A. Sandhar and R.K. Singh, Rapid and Efficient Synthesis of 2,3-Dihydro-1H-1,5-Benzodiazepines Catalyzed by Chloroacetic Acid Screened among Various Aliphatic Acids under Solvent Free Conditions, Chem. Sci. Trans., 2, 176 (2012); https://doi.org/10.7598/cst2013.315.
P. Kaur and R.K. Singh, Investigation of Various Green Chemistry Approaches for the Efficient Synthesis of Dialkyl-1,4-dihydro-4-(substituted phenyl)-2,6-dimethylpyridine-3,5-dicarboxylate, Chem. Sci. Trans., 2(S1), S295 (2013); https://doi.org/10.7598/cst2013.443.
Y. Zhao, S. Sharma, M. Huang, A. Sandhar, R.K. Singh and Y. Ma, Investigation of Various Organocatalysts for Improved and Efficient One Pot Synthesis of 2,3-Dihydro-1H-1,5-benzodiazepines under Solvent-Free Condition, Asian J. Chem., 26, 5116 (2014); https://doi.org/10.14233/ajchem.2014.16440.
T. Li, X. Zhai, D. Singh, R.K. Singh and X. Xu, Multicomponent One-pot Green Synthesis of 1-Amidoalkyl-2-naphthols Promoted by p-Nitrobenzoic Acid under Solvent-Free Condition, Asian J. Chem., 26, 5207 (2014); https://doi.org/10.14233/ajchem.2014.16707.
R.K. Singh, B. Singh, R. Duvedi and S. Kumar, Sulfanilic Acid: A Versatile and Efficient Catalyst among Various Organoacids Screened for the Synthesis of 1-Amidoalkyl-2-Naphthols under Solvent-Free Condition, Res. Chem. Intermed., 41, 4083 (2015); https://doi.org/10.1007/s11164-013-1513-5.
R.K. Singh, R. Bala and S. Kumar, Microwave Assisted Facile Synthesis of 1-Amidoalkyl-2-naphthols Catalyzed by Stannous Oxide Nano-particles, J. Indian Chem. Soc., 92, 1161 (2015).
Y. Zhao, X. Yu, M. Saini, Y. Ma and R.K. Singh, Highly Efficient Zinc Oxide Nanoparticles Catalyzed Green Synthesis of 1,5-Benzodiazepines under Solvent-Free Path, Asian J. Chem., 26, 8539 (2014); https://doi.org/10.14233/ajchem.2014.18319.
R.K. Singh, R. Bala and S. Kumar, An Efficient Synthesis of 1-Amidoalkyl-2-Naphthols Catalyzed by Zinc Oxide Nanoparticles Under Solvent-Free Conditions, Indian J. Chem., 55B, 381 (2016).
R.K. Singh and R. Duvedi, Environment-Friendly Green Chemistry Approaches for an Efficient Synthesis of 1-Amidoalkyl-2-Naphthols Catalyzed by Tannic Acid, Arab. J. Chem., 11, 91 (2018); https://doi.org/10.1016/j.arabjc.2014.08.022.
S. Chaudhary, S. Sharda, D.N. Prasad, S. Kumar and R.K. Singh, Synthetic Methodologies and Pharmacological Significance of 2-Aminobenzophenones as Versatile Building Block, Asian J. Org. Med. Chem, 3, 107 (2018); https://doi.org/10.14233/ajomc.2018.AJOMC-P136.