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Current Organocatalysis

Editor-in-Chief

ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

Research Article

Synthesis of Oxadiazole, Imidazole, Benzimidazole, Cyclohexano Analogues of 1, 5-benzodiazepines Through Phenoxyl/Phenylamino Linkage

Author(s): Mohd Amin Mir*

Volume 9, Issue 4, 2022

Published on: 03 October, 2022

Page: [297 - 304] Pages: 8

DOI: 10.2174/2212796816666220404151254

Price: $65

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Abstract

Aims: The study aims to synthesize oxadiazole, imidazole, benzimidazole, and cyclohexano analogues of 1, 5-benzodiazepines through phenoxyl/phenylamino linkage.

Background: It is worthwhile to mention that imidazoles, benzimidazoles, oxadiazoles, are analysed extensively mainly as per their ready availability, broad chemical reactivity, and wide spectrum of biochemical activities, like antimicrobial, anti-inflammatory, antitumor, anticonvulsant drugs, antitubercular medicines, and having an anti-HIV effect, etc.

Objective: The oxadiazole, imidazole, benzimidazole derivatives were synthesized via cyclohexano analogues of 1, 5-benzodiazepines through phenoxyl/phenylamino linkage.

Methods: The characteristic drift of our interest towards these molecules prompted us to think about the structural modification of [1, 5]-benzodiazepine compound by incorporating on its 2-position imidazole, benzimidazole, oxadiazole, nuclei through an aminophenyl or phenoxyl bridge to synthesize these novel heterocyclic analogues of 1, 5-benzodiazepines.

Results: These derivatives have been analysed by various spectrophometric techniques like UV, IR, NMR, and MS. The synthesis of these compounds via the mentioned methods is unique as cyclohexano analogues of 1, 5-benzodiazepines through phenoxyl/phenylamino is a totally new way of synthesis. The derivatives can be analysed for various properties in chemistry and pharmacology, as their parent compounds have many pharmacological properties.

Conclusion: The synthesis of these types of compounds does provide new hope to the medicinal and pharmaceutical industries. Therefore further efforts should be taken into consideration for the synthesis and analysis of their medicinal properties.

Keywords: Oxadiazole, Imidazole, Benzimidazoles, 1, 5-benzodiazepines, phenoxyl / phenylamino linkage, IR, 1H NMR

Graphical Abstract

[1]
Sengupta, P.; Mal, M.; Mandal, S.; Singh, J.; Maity, T.K. Evaluation of antibacterial and activity of some 1, 3, 4 oxadiazoles. Iranian J. Pharmacol. Therapeutics., 2008, 7(2), 165-167.
[2]
Bhardwaj, N.; Saraf, S.K.; Sharma, P.; Kumar, P. Syntheses, evaluation and characterization of some 1, 3, 4-oxadiazoles as antimicrobial agents. E-J. Chem., 2009, 6(4), 1133-1138.
[http://dx.doi.org/10.1155/2009/698023]
[3]
Kadi, A.A.; El-Brollosy, N.R.; Al-Deeb, O.A.; Habib, E.E.; Ibrahim, T.M.; El-Emam, A.A. Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. Eur. J. Med. Chem., 2007, 42(2), 235-242.
[http://dx.doi.org/10.1016/j.ejmech.2006.10.003] [PMID: 17129641]
[4]
Mickevicius, V.; Vaickelioniene, R.; Sapijanskaite, B. Synthesis of substituted 1, 3, 4-oxadiazole derivatives. Chem. Heterocycl. Compd., 2009, 45(2), 215-218.
[http://dx.doi.org/10.1007/s10593-009-0252-4]
[5]
Bentiss, F.; Lagrenee, M. A new synthesis of symmetrical 2, 5- disubstituted 1, 3, 4-oxadiazoles. J. Heterocycl. Chem., 1999, 36(4), 1029-1032.
[http://dx.doi.org/10.1002/jhet.5570360433]
[6]
Liras, S.; Allen, M.P.; Segelstein, B.E. A mild method for the preparation of 1, 3, 4-oxadiazoles: Triflic anhydride promoted cyclization of diacylhydrazines. Synth. Commun., 2000, 3(30), 437-443.
[http://dx.doi.org/10.1080/00397910008087340]
[7]
Gomes, D.; Borges, C.P.; Pinto, J.C. Study of the synthesis of poly (4, 4-diphenylether-1, 3, 4-oxadiazole) in solutions of poly (phosphor-ic acid). Polymer (Guildf.), 2001, 42(3), 851-865.
[http://dx.doi.org/10.1016/S0032-3861(00)00458-4]
[8]
Souldozi, A.; Ramazani, A. The reaction of (N-isocyanimino) triphenylphosphorane with benzoic acid derivatives: A novel synthesis of 2-aryl-1, 3, 4-oxadiazole derivatives. Tetrahedron Lett., 2007, 48(9), 1549-1551.
[http://dx.doi.org/10.1016/j.tetlet.2007.01.021]
[9]
Ramazani, A.; Abdian, B.; Nasrabadi, F.Z.; Rouhani, M. The reaction of N-isocyaniminotriphenyl phosphorane with biacetyl in the pres-ence of (E)-cinnamic acids: Synthesis of fully substituted 1, 3, 4-oxadiazole derivatives via intramolecular aza-wittig reactions of in situ generated imino phosphoranes. Phosphorus Sulfur Silicon Relat. Elem., 2013, 188(5), 642-648.
[http://dx.doi.org/10.1080/10426507.2012.700351]
[10]
Ramazani, A.; Zeinalia Nasrabadi, F.; Ahmadi, Y. One-pot, four-component synthesis of fully substituted 1, 3, 4-oxadiazole derivatives from (Isocyanoimino) triphenylphosphorane, a primary amine, an aromatic carboxylic acid, and chloroacetone. Helv. Chim. Acta, 2011, 94(6), 1024-1029.
[http://dx.doi.org/10.1002/hlca.201000356]
[11]
Ramazani, A.; Souldozi, A. Iminophosphorane-mediated one-pot synthesis of 1, 3, 4-oxadiazole derivatives. ARKIVOC, 2008, 16(16), 235-242.
[http://dx.doi.org/10.3998/ark.5550190.0009.g22]
[12]
Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications of the Most Relevant APIs, 3rd ed; Thieme Medical: New York, NY, USA, 1999.
[13]
Debus, H. Ueber die Einwirkung des Ammoniaks aufGlyoxal. Justus Liebigs Ann. Chem., 1958, 107(2), 199-208.
[http://dx.doi.org/10.1002/jlac.18581070209]
[14]
Woolley, D.W. Some biological effects produced by benzImidazole and their reversal by purines. J. Biol. Chem., 1944, 152(2), 225-232.
[http://dx.doi.org/10.1016/S0021-9258(18)72045-0]
[15]
Brink, N.G.; Flokers, K. Vitamin-B12. Vi. 5, 6-Dimethylbenzimidazole, a degradation product of vitamin-B12. J. Am. Chem. Soc., 1949, 71(8), 2951.
[http://dx.doi.org/10.1021/ja01176a532]
[16]
Epstein, S.S. Effect of some benzimidazoles on a vitamin B12-requiring alga. Nature, 1960, 188(4745), 143-144.
[http://dx.doi.org/10.1038/188143a0] [PMID: 13697028]
[17]
Nalage, S.V.; Kalyankar, M.B.; Patil, V.S.; Bhosale, S.V.; Deshmukh, S.U.; Pawar, R.P. An efficient non catalytic protocol for the synthesis of trisubstituted Imidazole in polyethylene glycol using microwaves. Open Catalysis J., 2010, 3, 58.
[18]
Lange, J.H.; van Stuivenberg, H.H.; Coolen, H.K.; Adolfs, T.J.; McCreary, A.C.; Keizer, H.G.; Wals, H.C.; Veerman, W.; Borst, A.J.; de Looff, W.; Verveer, P.C.; Kruse, C.G. Bioisosteric replacements of the pyrazole moiety of rimonabant: Synthesis, biological properties, and molecular modeling investigations of thiazoles, triazoles, and imidazoles as potent and selective CB1 cannabinoid receptor antago-nists. J. Med. Chem., 2005, 48(6), 1823-1838.
[http://dx.doi.org/10.1021/jm040843r] [PMID: 15771428]
[19]
Reddy, P.P.; Mukkanti, K.; Purandhar, K. AIPO4 mediated one-pot, four component synthesis of 1, 2, 4, 5-tetrasubsituted imidazoles under convectional heating and microwave irradiation. Rasayan J. Chem., 2010, 3, 335.
[20]
Bahrami, K.; Mehdi, K.M.; Naali, F. Mild and highly method for the synthesis of 2-arylbenzimidazoles, and 2-arylbenzothiazoles from resin bound esters. J. Org. Chem., 2008, 73, 6835.
[http://dx.doi.org/10.1021/jo8010232] [PMID: 18652508]
[21]
Janardhana, G.; Khadar, A.M.; Balakrishana, K.; Nalilu, S.K. Microwave assisted synthesis of 1, 3, 4-oxadizoles carrying benzImidazole moiety and their antimicrobial properties. Indian J. Chem., 2010, 48B, 1130.
[22]
Kande, K.D.; Amarasinghe, M.; Maier, B.; Shrivastva, A.; Jeffrey, L.G. One-pot synthesis of 1, 2, 4-oxadiazoles from carboxylic acid esters and amidoxime using potassium carbonate. Tetrahedron Lett., 2006, 47, 3629-3631.
[23]
Liang, GB; Danqing, DF An improved oxadiazole synthesis using peptide coupling reagents. Tetrahedron let, 1996, 37, 6627.
[http://dx.doi.org/10.1016/S0040-4039(96)01492-X]
[24]
Fuloria, N.K.; Singh, V.; Shaharyar, M.; Ali, M. Synthesis and antimicrobial evaluation of some new oxadiazoles derived from phe-nylpropionohydrazides. Molecules, 2009, 14(5), 1898-1903.
[http://dx.doi.org/10.3390/molecules14051898] [PMID: 19471209]
[25]
Korzhavina, O.B.; Ryabukhin, Y.I.; Garnovskii, A.D.; Shavel, I.I. Synthesis of 4-oxo-1,3-benzothiazines and their salts. Chem. Heterocycl. Compd., 1985, 21(4), 472-473.
[http://dx.doi.org/10.1007/BF00504417]
[26]
Wipf, P.; Fletcher, J.M.; Scarone, L. Mirowave promoted oxazole synthesis: Cyclocondensation cascade of oximes and acyl chlorides. Tetrahedron Lett., 2005, 46(33), 5463-5466.
[http://dx.doi.org/10.1016/j.tetlet.2005.06.063]

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