AN UPDATE ON THE SYNTHESIS OF BENZOXAZOLES
DOI:
https://doi.org/10.22159/ajpcr.2017.v10i10.19457Keywords:
Benzoxazoles, Chemistry synthesis, Biological activitiesAbstract
Benzoxazoles being structurally similar to bases adenine and guanine interact with biomolecules present in living systems. These compounds possess antimicrobial, central nervous system activities, antihyperglycemic potentiating activity, analgesic, and anti-inflammatory activity. It can also be used as starting material for other bioactive molecules. Modifications in structure and the biological profiles of new generations of benzoxazoles were found to be more potent with enhanced biological activity. Considering all these, we have prepared this review and discussed the synthesis and biological activities of benzoxazoles.
Downloads
References
Barton D, Ollis WD. Comprehensive Organic Chemistry. Vol. 1. England: Pergamon Press; 1979. p. 641.
Chaudhary M, Pareek D, Pareek PK, Kant R, Ojha KG, Pareek A. Synthesis of some new biologically active benzothiazole derivatives containing benzimidazole and imidazoline moieties. Chem Inf 2011;42(23):131-6.
Sambaiah T, Reddy KK. Synthesis of 2-Aryl [1, 2, 4] triazolo [5, 1-b] benzoxazoles by oxidative cyclization of N-(benzoxazol-2-yl) benzamidines. Synthesis 1990;1990(5):422-4.
Oren I, Temiz O, Yalçin I, Sener E, Akin A, Uçartürk N. Synthesis and microbiological activity of 5(or 6)-methyl-2-substituted benzoxazole and benzimidazole derivatives. Arzneimittelforschung 1997;47(12):1393-7.
Elnima EI, Zubair MU, Al-Badr AA. Antibacterial and antifungal activities of benzimidazole and benzoxazole derivatives. Antimicrob Agents Chemother 1981;19(1):29-32.
El-Sherief HA, Mahmoud AM, Abdel-Rahman AE, El-Naggar GM. Synthesis of some new benzoxazole, benzothiazole and benzimidazole derivatives with biological activity. Chem Inform 1983;14(31):28-37.
Sarangapani M, Reddy VM. Phramacological evaluation of 1-(N, N-disubstituted aminomethyl)-3-Imino-(2-phenyl-3, 4-dihydro-4-oxo-quinazolin-3-Yl) indolin-2-ones. Indian J Pharm Sci 1996;58(4):147.
Bahadur S, Pandey K. Synthesis of ethyl P-(2-benzoxazolyl) phenoxyacetate and corresponding hydrazides. Chem Inform 1982;13(3):46-54.
Katsura Y, Inoue Y, Tomoi M, Takasugi H. Studies on antiulcer drugs. V. Synthesis and antiulcer activity of aralkylbenzazoles. Chem Pharm Bull (Tokyo) 1992;40(8):2062-74.
Matthews CJ, Leese TA, Clegg W, Elsegood MR, Horsburgh L, Lockhart JC. A route to bis (benzimidazole) ligands with built-in asymmetry: Potential models of protein binding sites having histidines of different basicity. Inorg Chem 1996;35(26):7563-71.
Yamada M, Sato Y, Kobayashi K, Konno F, Soneda T, Watanabe T. A new 5-HT3 receptor ligand. II. Structure-activity analysis of 5-HT3 receptor agonist action in the gut. Chem Pharm Bull 1998;46(3):445-51.
Kövér J, TÃmár T, Tompa J. Novel and efficient synthesis of 6-chloro-2-(substituted amino) benzoxazoles. Synthesis 1994;1994(11):1124-6.
Hein DW, Alheim RJ, Leavitt JJ. The use of polyphosphoric acid in the synthesis of 2-aryl-and 2-alkyl-substituted benzimidazoles, benzoxazoles and benzothiazoles1. J Am Chem Soc 1957;79(2):427-9.
Katritzky AR. Highlights from 50 years of heterocyclic chemistry. J Heterocycl Chem 1994;31(3):569-602.
Rostamizadeh S, Housaini SG. Microwave-assisted preparation of 2-substituted benzothiazoles. Phosphorus Sulfur Silicon Relat Elem 2005;180(5-6):1321-6.
Larina L, Lopyrev V. Synthesis of nitrobenzazoles. In: Nitroazoles: Synthesis, Structure and Applications. New York: Springer; 2009. p. 81-156.
Grundmann C, Kreutzberger A. Triazines. XIII. The ring cleavage of s-triazine by primary amines. A new method for the synthesis of heterocycles1, 2. J Am Chem Soc 1955;77(24):6559-62.
Jenkins G, Knevel A, Davis C. Notes. A new synthesis of the benzothiazole and benzoxazole rings. J Org Chem 1961;26(1):274.
Hojati SF, Maleki B, Beykzadeh Z. 1, 3-dibromo-5, 5-dimethylhydantoin as an efficient homogeneous catalyst for synthesis of benzoxazoles, benzimidazoles, and oxazolo [4, 5-b] pyridines. Monat Chem Chem Mon 2011;142(1):87-91.
Ito Y, Inubushi Y, Zenbayashi M, Tomita S, Saegusa T. Synthetic reactions by complex catalysts. XXXI. Novel and versatile method of heterocycle synthesis. J Am Chem Soc 1973;95(13):4447-8.
Ito Y, Ito I, Hirao T, Saegusa T. Synthetic reactions by complex catalysts XXXV. A facile synthetic method of cyclic imino ethers and imino thioethers. Synth Commun 1974;4(2):97-103.
Ferris JP, Antonucci FR, Trimmer RW. Mechanism of the photoisomerization of isoxazoles and 2-cyanophenol to oxazoles. J Am Chem Soc 1973;95(3):919-20.
Bhawal BM, Mayabhate SP, Likhite AP, Deshmukh AR. Use of zeolite catalysts for efficient synthesis of benzoxazoles via Beckmann rearrangement. Synth Commun 1995;25(21):3315-21.
Poissonnet G. A simple and convenient synthesis of 1, 2-benzoxazoles via intramolecular mitsunobu reaction from salicylaldoximes and orthohydroxyarylketoximes. Synth Commun 1997;27(22):3839-46.
Koyama E, Yang G, Hiratani K. A novel synthesis of bis (benzoxazole) derivatives via tandem claisen rearrangement. Tetrahedron Lett 2000;41(42):8111-6.
Novel Heteroaryl Substituted Benzoxazoles No. WO/2007/149030.
El-Saghier AM, Khodairy A. New synthetic approaches to condensed and spiro coumarins: Coumarin-3-thiocarboxamide as building block for the synthesis of condensed and spiro coumarins. Phosphorus Sulfur Silicon Relat Elem 2000;160(1):105-19.
Khan RH, Rastogi RC. Synthesis and biological activity of 2-(4-aryl-2-thiazolylamino) benzothiazoles/benzoxazoles/benzimidazoles/imidazolidines. Chem Inform 1989;20(43):529-31.
Saitz C, RodrÃguez H, Márquez A, Canete A, Jullian C, Zanocco A. New synthesis of naphtho-and benzoxazoles: Decomposition of naphtho-and benzoxazinones with KOH. Synth Commun 2001;31(1):135-40.
Dang TD, Hudson LS, Feld W. Synthesis and characterization of aromatic benzoxazoles containing allylether pendent groups. Polym Prepr (USA) 2000;41(1):103-4.
Sato Y, Yamada M, Yoshida S, Soneda T, Ishikawa M, Nizato T, et al. Benzoxazole derivatives as novel 5-HT3 receptor partial agonists in the gut. J Med Chem 1998;41(16):3015-21.
Skinner WA, Gualtiere F, Brody G, Fieldsteel AH. Antiviral agents. 1. Benzothiazole and benzoxazole analogs of 2-(alpha.-hydroxybenzyl) benzimidazole. J Med Chem 1971;14(6):546-9.
Kunz KR, Taylor EW, Hutton HM, Blackburn BJ. A simple and convenient synthesis of 5-substituted benzoxazoles. Org Prep Proced Int 1990;22(5):613-8.
Konda S. Development of Biologically Active Benz Oxazole Derivatives. US: Lulu; 2015. 35. Jois YH, Gibson HW. Difunctional heterocycles: A convenient one pot synthesis of novel bis (benzoxazoles) from bis (o-aminophenols). J Heterocycl Chem 1992;29(5):1365-8.
Niementowski S. New methods for the preparation of the anhydro compounds. Ber Deutsch Chem Ges 1897;30(3):3062-71.
Wang F, Hauske JR. Solid-phase synthesis of benzoxazoles via mitsunobu reaction. Tetrahedron Lett 1997;38(37):6529-32.
Watanabe KA. The chemistry of C-nucleosides. In: Chemistry of Nucleosides and Nucleotides. US: Springer; 1994. p. 421-535.
Kosaka T, Ochiai K, Ohba S, Wakabayashi T, Murota SI. A novel series of highly potent 5-lipoxygenase inhibitors; 2-aryldienylbenzoxazoles. Bioorg Med Chem Lett 1995;5(1):35-8.
Hari A, Karan C, Rodrigues WC, Miller BL. Extending the scope of chromium-manganese redox-coupled reactions: A one-pot synthesis of benzoxazoles. J Org Chem 2001;66(3):991-6.
Haugwitz RD, Angel RG, Jacobs GA, Maurer BV, Narayanan VL, Cruthers LR, et al. Antiparasitic agents. 5. Synthesis and anthelmintic activities of novel 2-heteroaromatic-substituted isothiocyanatobenzoxazoles and-benzothiazoles. J Med Chem 1982;25(8):969-74.
Gouloumis A, Liu SG, Sastre A, Vazquez P, Echegoyen L, Torres T. Synthesis and electrochemical properties of phthalocyanine-fullerene hybrids. Chemistry 2000;6(19):3600-7.
Qian X, Li Z, Song G, Li Z. Yellow HgO as an efficient cyclodesulfurising agent in the synthesis of 2-substituted aminobenzoxazoles from N-(2-hydroxyphenyl)-N’-phenylthioureas. J Cheml Res 2001;4:138-9.
Olagbemiro TO, Agho MO, Abayeh OJ, Amupitan JO. Facile synthesis of 2-substituted benzoxazoles via ketenes. Rec Trav Chim Pays Bas 1996;115(6):337-8.
Omar AM, Mohsen ME, Ashour FA, Bourdais J. The cyelodesulfurization of thio-compounds. Part XVII. Synthesis of some novel 2-substituted amino-3, 4-dihydro-5H-1, 3, 4-benzotriazepin-5-ones by cyelodesulfurization of thiosemicarbazides with dicyclohexylearbodiimide (DCCD). J Heterocycl Chem 1979;16(7):1435-8.
Kondo T, Yang S, Huh KT, Kobayashi M, Kotachi S, Watanabe Y. Ruthenium complex-catalyzed facile synthesis of 2-substituted benzo-azoles. Chem Lett 1991;20(7):1275-8.
Katritzky AR, Rees CW. Comprehensive Heterocyclic Chemistry. Oxford: Pergamon Press; 1984.
Kaur A, Sharad W, Pathak DP. Benzoxazole: The molecule of diverse pharmacological importance. Int J Pharm Pharm Sci 2014;7(1):16-23.
Paralapalli AD, Kishore A, Cidda M, Manda S. Antiinflammatory and antioxidant activities of 2-amino-N-(substituted alkyl) benzoxazole-5-carboxamide derivatives. Int J Pharm Pharm Sci 2014;6(7):311-4.
Published
How to Cite
Issue
Section
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.
