Synthesis of some benzothiazoles by developing a new protocol using urea nitrate as a catalyst and their antimicrobial activities

References

• Keri RS, Patil MR, Patil SA, et al. A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry. Eur J Med Chem. 2015;89:207–251. doi: 10.1016/j.ejmech.2014.10.059
   PubMed Web of Science ®Google Scholar
• Sahin B, Yaglioglu AS, Ceylan M. Synthesis and cytotoxic activities of novel 2-(1, 5-bis (aryl) penta-1, 4-dien-2-yl) benzo[d] thiazole derivatives. Org Comm. 2016;9:65–72.
   Google Scholar
• Liu DC, Zhang HJ, Jin CM, et al. Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticonvulsant agents. Molecules. 2016;21:164–171. doi: 10.3390/molecules21020164
   PubMed Web of Science ®Google Scholar
• Ongarora DS, Strydom N, Wicht K, et al. Antimalarial benzoheterocyclic 4-aminoquinolines: structure–activity relationship, in vivo evaluation, mechanistic and bioactivation studies. Bioorg Med Chem. 2015;23:5419–5432. doi: 10.1016/j.bmc.2015.07.051
   PubMed Web of Science ®Google Scholar
• Kamo M, Tateishi H, Koga R, et al. Synthesis of the biotinylated anti-HIV compound BMMP and the target identification study. Bioorg Med Chem Lett. 2016;26:43–45. doi: 10.1016/j.bmcl.2015.11.036
   PubMed Web of Science ®Google Scholar
• Khan KM, Mesaik MA, Abdalla OM, et al. The immunomodulation potential of the synthetic derivatives of benzothiazoles: implications in immune system disorders through in vitro and in silico studies. Bioorg Chem. 2016;64:21–28. doi: 10.1016/j.bioorg.2015.11.004
   PubMed Web of Science ®Google Scholar
• Singh M, Singh SK, Gangwar M, et al. Design, synthesis and mode of action of novel 2-(4-aminophenyl) benzothiazole derivatives bearing semicarbazone and thiosemicarbazone moiety as potent antimicrobial agents. Med Chem Res. 2016;25:263–282. doi: 10.1007/s00044-015-1479-5
   Web of Science ®Google Scholar
• Jordan AD, DesJarlais RL, Hlasta DJ, et al. Substituted benzothiazole and benzoxazole derivatives useful as inhibitors of DPP-1. United States patent US 8,481,547. 2013.
   Google Scholar
• Shafi S, Alam MM, Mulakayala N, et al. Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: their anti-inflammatory and anti-nociceptive activities. Eur J Med Chem. 2012;49:324–333. doi: 10.1016/j.ejmech.2012.01.032
   PubMed Web of Science ®Google Scholar
• Brown HD. US Patent 3,278,547. 1966. Chem. Abstr. 1966;65:18593.
   Google Scholar
• Jeong CY, Choi JI, Yoon MH. Roles of serotonin receptor subtypes for the antinociception of 5-HT in the spinal cord of rats. Eur J Pharmacol. 2004;502:205–211. doi: 10.1016/j.ejphar.2004.08.048
   PubMed Web of Science ®Google Scholar
• Netalkar PP, Netalkar SP, Budagumpi S, et al. Synthesis, crystal structures and characterization of late first row transition metal complexes derived from benzothiazole core: anti-tuberculosis activity and special emphasis on DNA binding and cleavage property. Eur J Med Chem. 2014;79:47–56. doi: 10.1016/j.ejmech.2014.03.083
   PubMed Web of Science ®Google Scholar
• Yurttaş L, Tay F, Demirayak Ş. Synthesis and antitumor activity evaluation of new 2-(4-aminophenyl) benzothiazole derivatives bearing different heterocyclic rings. J Enzyme Inhib Med Chem. 2015;30:458–465. doi: 10.3109/14756366.2014.945168
   PubMed Web of Science ®Google Scholar
• Cifelli JL, Chung TS, Liu H, et al. Benzothiazole amphiphiles ameliorate amyloid β-related cell toxicity and oxidative stress. ACS Chem Neurosci. 2016;7:682–688. doi: 10.1021/acschemneuro.6b00085
   PubMed Web of Science ®Google Scholar
• Ivanov SK, Yuritsyn VS. Neftekhimiya 1971, 11, 99. In Chem. Abstr 1971;74:124487.
   Google Scholar
• Avagyan R, Luongo G, Thorsén G, et al. Benzothiazole, benzotriazole, and their derivates in clothing textiles—a potential source of environmental pollutants and human exposure. Environ Sci Pollut Res. 2015;22:5842–5849. doi: 10.1007/s11356-014-3691-0
   PubMed Web of Science ®Google Scholar
• Muthusubramanian L, Rao VS, Mitra RB. Efficient synthesis of 2-(thiocyanomethylthio) benzothiazole. J Clean Prod. 2001;9:65–67. doi: 10.1016/S0959-6526(00)00031-7
   Google Scholar
• Spies RB, Andresen BD, Rice Jr DW. Benzthiazoles in estuarine sediments as indicators of street runoff. Nature. 1987;327:697–699. doi: 10.1038/327697a0
   Web of Science ®Google Scholar
• Yoshida H, Nakao R, Nohta H, et al. Chemiluminescent properties of some luminol-related compounds—part 3. Dyes Pigm. 2000;47:239–245. doi: 10.1016/S0143-7208(00)00080-2
   Web of Science ®Google Scholar
• Zhang XH, Wong OY, Gao ZQ, et al. A new blue-emitting benzothiazole derivative for organic electroluminescent devices. Mater Sci Eng B. 2001;85:182–185. doi: 10.1016/S0921-5107(01)00607-9
   Web of Science ®Google Scholar
• Petkov I, Deligeorgiev T, Markov P, et al. Effect of some 2-arylbenzothiazoles on the photo-degradation of poly(vinyl chloride). Polym Degrad Stabil. 1991;33:53–66. doi: 10.1016/0141-3910(91)90029-Q
   Web of Science ®Google Scholar
• Bougrin K, Loupy A, Soufiaoui M. Trois nouvelles voies de synthèse des dérivés 1,3-azoliques sous micro-ondes. Tetrahedron. 1998;54:8055–8064. doi: 10.1016/S0040-4020(98)00431-1
   Web of Science ®Google Scholar
• Kodomari M, Tamaru Y, Aoyama T. Solvent-free synthesis of 2-aryl and 2-alkylbenzothiazoles on silica gel under microwave irradiation. Synth Commun. 2004;34:3029–3036. doi: 10.1081/SCC-200026663
   Web of Science ®Google Scholar
• Ghashang M. Bismuth nitrate as an efficient catalyst for the preparation of 2-arylbenzothiazole derivatives. Res Chem Intermed. 2014;4:1669–1674. doi: 10.1007/s11164-013-1072-9
   Web of Science ®Google Scholar
• Abdollahi-Alibeik M, Poorirani S. Perchloric acid–doped polyaniline as an efficient and reusable catalyst for the synthesis of 2-substituted benzothiazoles. Phosphorus Sulfur Silicon Relat Elem. 2009;184:3182–3190. doi: 10.1080/10426500802705453
   Web of Science ®Google Scholar
• Chakraborti AK, Rudrawar S, Jadhav KB, et al. “On water” organic synthesis: a highly efficient and clean synthesis of 2-aryl/heteroaryl/styryl benzothiazoles and 2-alkyl/aryl alkyl benzothiazolines. Green Chem. 2007;9:1335–1340. doi: 10.1039/b710414f
   Web of Science ®Google Scholar
• Al-Qalaf F, Mekheimer RA, Sadek KU. Cerium (IV) ammonium nitrate (CAN) catalyzed one-pot synthesis of 2-arylbenzothiazoles. Molecules. 2008;13:2908–2914. doi: 10.3390/molecules13112908
   PubMed Web of Science ®Google Scholar
• Chandrachood PS, Garud DR, Gadakari TV, et al. A cobalt nitrate/hydrogen peroxide system as an efficient reagent for the synthesis of 2-aryl benzimidazoles and benzothiazoles. Acta Chim Slov. 2011;58:367–371.
   PubMed Web of Science ®Google Scholar
• Rostamizadeh S, Housaini SG. Microwave-assisted preparation of 2-substituted benzothiazoles. Phosphorus Sulfur Silicon Relat Elem. 2005;180:1321–1326. doi: 10.1080/10426500590912268
   Web of Science ®Google Scholar
• Li Y, Wang YL, Wang JY. A simple iodine-promoted synthesis of 2-substituted benzothiazoles by condensation of aldehydes with 2-aminothiophenol. Chem Lett. 2006;35:460–461. doi: 10.1246/cl.2006.460
   Web of Science ®Google Scholar
• Chen GF, Zhang LY, Jia HM, et al. Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by silica sulfuric acid. Res Chem Intermed. 2013;39:2077–2086. doi: 10.1007/s11164-012-0739-y
   Web of Science ®Google Scholar
• Niralwad KS, Shingate BB, Shingare MS. Solid-phase synthesis of 2-arylbenzothiazole using silica sulfuric acid under microwave irradiation. Bull Korean Chem Soc. 2010;31:981–983. doi: 10.5012/bkcs.2010.31.04.981
   Web of Science ®Google Scholar
• Matsushita H, Lee SH, Joung M, et al. Smart cleavage reactions: the synthesis of benzimidazoles and benzothiazoles from polymer-bound esters. Tetrahedron Lett. 2004;45:313–316. doi: 10.1016/j.tetlet.2003.10.168
   Web of Science ®Google Scholar
• Boger DL. A convenient preparation of 2-substituted benzothiazoles. J Org Chem. 1978;43:2296–2297. doi: 10.1021/jo00405a050
   Web of Science ®Google Scholar
• Sharghi H, Asemani O. Methanesulfonic acid/SiO2 as an efficient combination for the synthesis of 2-substituted aromatic and aliphatic benzothiazoles from carboxylic acids. Synth Commun. 2009;39:860–867. doi: 10.1080/00397910802431214
   Web of Science ®Google Scholar
• Zhu C, Akiyama T. One-pot tandem approach for the synthesis of benzothiazoles from benzyl halides. Synlett. 2010;16;2457–2460.
   Google Scholar
• Alagille D, Baldwin RM, Tamagnan GD. One-step synthesis of 2-arylbenzothiazole (‘BTA’) and -benzoxazole precursors for in vivo imaging of β-amyloid plaques. Tetrahedron Lett. 2005;46:1349–1351. doi: 10.1016/j.tetlet.2004.12.111
   Web of Science ®Google Scholar
• Siddappa C, Kambappa V, Umashankara M, et al. One-pot approach for the synthesis of 2-aryl benzothiazoles via a two-component coupling of gem-dibromomethylarenes and o-aminothiophenols. Tetrahedron Lett. 2011;52:5474–5477. doi: 10.1016/j.tetlet.2011.08.055
   Web of Science ®Google Scholar
• Evindar G, Batey RA. Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides. J Org Chem. 2006;71:1802–1808. doi: 10.1021/jo051927q
   PubMed Web of Science ®Google Scholar
• Tale RH. Novel synthesis of 2-arylbenzothiazoles mediated by ceric ammonium nitrate (CAN). Org Lett. 2002;4:1641–1642. doi: 10.1021/ol020027i
   PubMed Web of Science ®Google Scholar
• Bose DS, Idrees M, Srikanth B. Synthesis of 2-arylbenzothiazoles by DDQ-promoted cyclization of thioformanilides; a solution-phase strategy for library synthesis. Synthesis. 2007;6:819–823. doi: 10.1055/s-2007-965929
   Web of Science ®Google Scholar
• Mu XJ, Zou JP, Zeng RS, et al. Mn(III)-promoted cyclization of substituted thioformanilides under microwave irradiation: a new reagent for 2-substituted benzothiazoles. Tetrahedron Lett. 2005;46:4345–4347. doi: 10.1016/j.tetlet.2005.04.090
   Web of Science ®Google Scholar
• Raghavendra GM, Ramesha AB, Revanna CN, et al. One-pot tandem approach for the synthesis of benzimidazoles and benzothiazoles from alcohols. Tetrahedron Lett. 2011;52:5571–5574. doi: 10.1016/j.tetlet.2011.08.037
   Web of Science ®Google Scholar
• Mathis CA, Wang Y, Holt DP, et al. Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents. J Med Chem. 2003;46:2740–2754. doi: 10.1021/jm030026b
   PubMed Web of Science ®Google Scholar
• Kumar P, Bhatia R, Kumar D, et al. An economic, simple and convenient synthesis of 2-aryl/heteroaryl/styryl/alkylbenzothiazoles using SiO2–HNO3. Res Chem Intermed. 2015;41:4283–4292. doi: 10.1007/s11164-013-1529-x
   Web of Science ®Google Scholar
• Vogel AI. A textbook of practical organic chemistry. London: Longmans; 1971, p. 442.
   Google Scholar
• Sura TP, Ramana MM, Kudav NA. Urea nitrate: a reagent for regioselective nitration of aromatic amines. Synth Commun. 1988;18:2161–2165. doi: 10.1080/00397918808068287
   Web of Science ®Google Scholar
• Mundla SR. Regioselective synthesis of 4-halo ortho-dinitrobenzene derivatives. Tetrahedron Lett. 2000;41:4277–4279. doi: 10.1016/S0040-4039(00)00587-6
   Web of Science ®Google Scholar
• Perumal PT, Anniyappan M, Muralidharan D. Deprotection of oximes using urea nitrate under microwave irradiation. J Chem Sci. 2004;116:261–264. doi: 10.1007/BF02708276
   Web of Science ®Google Scholar
• Anniyappan M, Nagarajan R, Perumal PT. Urea nitrate catalyzed imino Diels-Alder reactions: synthesis of cyclopentaquinolines, pyranoquinolines, and furoquinoline derivatives. Synth Commun. 2002;32:99–103. doi: 10.1081/SCC-120001514
   Web of Science ®Google Scholar
• Anniyappan M, Muralidharan D, Perumal PT. A novel application of the oxidizing properties of urea nitrate and peroxydisulfate-cobalt(II): aromatization of NAD(P)H model Hantzsch 1,4-dihydropyridines. Tetrahedron. 2002;58:5069–5073. doi: 10.1016/S0040-4020(02)00461-1
   Web of Science ®Google Scholar
• Almog J, Klein A, Sokol A, et al. Urea nitrate and nitrourea: powerful and regioselective aromatic nitration agents. Tetrahedron Lett. 2006;47:8651–8652. doi: 10.1016/j.tetlet.2006.10.027
   Web of Science ®Google Scholar
• Nagarajan R, Muralidharan D, Perumal PT. A new and facile method for the synthesis of nitrocarbazoles by urea nitrate. Synth Commun. 2004;34:1259–1264. doi: 10.1081/SCC-120030313
   Web of Science ®Google Scholar
• Ghorbani-Choghamarani A, Nikoorazm M, Goudarziafshar H, et al. A mild procedure for the preparation of o-nitrophenols by nitro urea or ammonium nitrate in the presence of silica sulfuric acid (SiO2-OSO3H). Chin J Chem. 2011;29:731–734. doi: 10.1002/cjoc.201190148
   Web of Science ®Google Scholar
• Verma S, Pandita S, Jain SL. Microwave assisted synthesis of nitro phenols from the reaction of phenols with urea nitrate under acid-free conditions. Tetrahedron Lett. 2014;55:1320–1322. doi: 10.1016/j.tetlet.2013.12.114
   Web of Science ®Google Scholar
• Shahid HA, Jahangir S, Yousuf S, et al. Synthesis, crystal structure, structural characterization and in vitro antimicrobial activities of 1-methyl-4-nitro-1H-imidazole. Arab J Chem. 2016;9:668–675. doi: 10.1016/j.arabjc.2014.11.001
   Web of Science ®Google Scholar
• Aneja KR, Sharma C, Joshi R. In vitro efficacy of amaltas (Cassia fistula L.) against the pathogens causing otitis externa. Jundishapur J Microbiol. 2011;4:175–184.
   Web of Science ®Google Scholar
• Prakash O, Aneja DK, Hussain K, et al. Synthesis and biological evaluation of dihydroindeno and indeno [1,2-e] [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazines as antimicrobial agents. Eur J Med Chem. 2011;46(10):5065–5073. doi: 10.1016/j.ejmech.2011.08.019
   PubMed Web of Science ®Google Scholar
• Chandna N, Kapoor JK, Grover J, et al. Pyrazolylbenzyltriazoles as cyclooxygenase inhibitors: synthesis and biological evaluation as dual anti-inflammatory and antimicrobial agents. New J Chem. 2014;38:3662–3672. doi: 10.1039/C4NJ00226A
   Web of Science ®Google Scholar