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Abstract
Benzodiazepine-2-one moiety consists of a seven-membered heterocyclic ring, a derivative of benzodiazepine group, that works in the central nervous system and used for a variety of medical conditions, such as anxiety, seizures and alcohol withdrawal. Microwave assisted synthesis of certain medically important benzodiazepin-2-ones was carried out using hexamine and ammonium chloride starting from 2-aminobenzophenones. Feasibility and optimization of the reaction conditions under closed vessel CEM microwave synthesizer provide the desired product with excellent yields (~90%), within minutes of focused microwave irradiation, without the use of catalyst, thereby, revealing the benefit of saving energy and time.
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References
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References
V. Lisowski, F. Fabis, A. Pierre, D.H. Caignard, P. Renard and S.J. Rault, Synthesis of New Aromatic Pyrrolo[2,1- c] [1,4]benzodiazepines and Pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepines as Anti-tumoral Agents, Enzyme Inhib. Med. Chem., 17, 403 (2002); https://doi.org/10.1080/1475636021000005712
A. Pajzderska, M.A. Gonzalez, J.P. Embs, J. Mielcarek and J.W. Wasicki, Dynamics of an Amorphous Pharmacologically Active Compound–Diazepam: A QENS Study Combined with Molecular Dynamics Simulations, RSC Adv., 7, 35504 (2017); https://doi.org/10.1039/C7RA06133A
D. Fluyau, N. Revadigar and B.E. Manobianco, Challenges of the Pharmacological Management of Benzodiazepine Withdrawal, Dependence and Discontinuation, Therap. Adv. Psychopharmacol., 8, 147 (2018); https://doi.org/10.1177/2045125317753340
G. Mohiuddin, P.S. Reddy, K. Ahmed and C.V. Ratnam, Recent Advances in the Synthesis of Annelated 1,4-Benzodiazepines, Heterocycles, 24, 3489 (1986); https://doi.org/10.3987/R-1986-12-3489
S. Fustero, J. González and C. del Pozo, 1,4-Benzodiazepine N-Nitrosoamidines: Useful Intermediates in the Synthesis of Tricyclic Benzodiazepines, Molecules, 11, 583 (2006); https://doi.org/10.3390/11080583
K. Kim, S.K. Volkman and J.A. Ellman, Synthesis of 3-Substituted 1,4-Benzodiazepin-2-ones, J. Braz. Chem. Soc., 9, 375 (1998); https://doi.org/10.1590/S0103-50531998000400010
A. Barthel, L. Trieschmann, D. Ströhl, R. Kluge, G. Böhm and R. Csuk, Synthesis of Dimeric Quinazolin-2-one, 1,4-Benzodiazepin-2-one, and Isoalloxazine Compounds as Inhibitors of Amyloid Peptides Association, Arch. Pharm., 342, 445 (2009); https://doi.org/10.1002/ardp.200800196
G. Laconde, M. Amblard and J. Martinez, Unexpected Reactivity of N-Acyl-Benzotriazoles with Aromatic Amines in Acidic Medium (ABAA Reaction), Eur. J. Org. Chem., 85 (2019); https://doi.org/10.1002/ejoc.201801567
P.S. Fier and A.M. Whittaker, An Atom-Economical Method To Prepare Enantiopure Benzodiazepines with N-Carboxyanhydrides, Org. Lett., 19, 1454 (2017); https://doi.org/10.1021/acs.orglett.7b00417
M.W. Campbell, J.S. Compton, C.B. Kelly and G.A. Molander, Three-Component Olefin Dicarbofunctionalization Enabled by Nickel/Photoredox Dual Catalysis, J. Am. Chem. Soc., 141, 20069 (2019); https://doi.org/10.1021/jacs.9b08282
G. Mwande-Maguene, J. Jakhlal, J.-B. Lekana-Douki, E. Mouray, T. Bousquet, S. Pellegrini, P. Grellier, F.S.T. Ndouo, J. Lebibi and L. Pelinski, One-Pot Microwave-Assisted Synthesis and Antimalarial Activity of Ferrocenylbenzodiazepines, New J. Chem., 35, 2412 (2011); https://doi.org/10.1039/c1nj20551j
E. Lattmann, D.C. Billington, D.R. Poyner, P. Arayarat, S.B. Howitt, S. Lawrence and M. Offel, Combinatorial Solid Phase Synthesis of Multiply Substituted 1,4-Benzodiazepines and Affinity Studies on the CCK 2 Receptor (Part 1), Drug Des. Discov., 18, 9 (2002); https://doi.org/10.3109/10559610213504
T.A. Keating and R.W. Armstrong, Postcondensation Modifications of Ugi Four-Component Condensation Products: 1-Isocyanocyclohexene as a Convertible Isocyanide. Mechanism of Conversion, Synthesis of Diverse Structures, and Demonstration of Resin Capture, J. Am. Chem. Soc., 118, 2574 (1996); https://doi.org/10.1021/ja953868b
R. Mohd, M. Ravinesh, H. Asif and A. Bahar, Synthesis of Some Novel C3 Substituted New Diazo[1,4]benzodiazepine-2-one Derivatives as Potent Anticonvulsants, Chem. Sci. J., 5, 1 (2010).
K.C. Majumdar, K. Ray, S. Ganai and T. Ghosh, Catalyst-Free 1,3-Dipolar Cycloaddition: An Efficient Route for the Formation of the 1,2,3-Triazole-Fused Diazepinone Framework, Synthesis, 858 (2010); https://doi.org/10.1055/s-0029-1218610
N. Sakai, A. Watanabe, R. Ikeda, Y. Nakaike and T. Konakahara, Me3SiCl-Promoted Intramolecular Cyclization of Aromatic Compounds Tethered with N,O-Acetals Leading to the Facile Preparation of 1,4-Benzodiazepine Skeletons, Tetrahedron, 66, 8837 (2010); https://doi.org/10.1016/j.tet.2010.09.077
P. Lecinska, N. Corres, D. Moreno, M. Garcia-Valverde, S. Marcaccini and T. Torroba, Synthesis of Pseudopeptidic (S)-6-Amino-5-oxo-1,4-diazepines and (S)-3-Benzyl-2-oxo-1,4-benzodiazepines by an Ugi 4CC Staudinger/Aza-Wittig Sequence, Tetrahedron, 66, 6783 (2010); https://doi.org/10.1016/j.tet.2010.06.062