A convenient [hydroxy(tosyloxy)iodo]benzene-mediated one-pot synthesis of 2-arylimidazo[2,1-b]benzothiazoles

References

• Furlan A, Colombo F, Kover A, Issaly N, Tintori C, Angeli L, Leroux V, Letard S, Amat M, Asses Y, Maigret B, Dubreuil P, Botta M, Dono R, Bosch J, Piccolo O, Passarella D, Maina F. Identification of new aminoacid amides containing the imidazo[2,1-b]benzothiazol-2-ylphenyl moiety as inhibitors of tumorigenesis by oncogenic Met signaling. Eur J Med Chem. 2012;47:239–254. doi: 10.1016/j.ejmech.2011.10.051
   PubMed Web of Science ®Google Scholar
• Al-Tel TH, Al-Qawasmeh RA, Zaarour R. Design, synthesis and in vitro antimicrobial evaluation of novel imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzothiazole motifs. Eur J Med Chem. 2011;46:1874–1881. doi: 10.1016/j.ejmech.2011.02.051
   PubMed Web of Science ®Google Scholar
• Palkar M, Noolvi M, Sankangoud R, Maddi V, Gadad A, Nargund LVG. Synthesis and antibacterial activity of a novel series of 2,3-diaryl-substituted-imidazo(2,1-b)-benzothiazole derivatives. Archiv der Pharmazie. 2010;343:353–359. doi: 10.1002/ardp.200900260
   Web of Science ®Google Scholar
• Malik JK, Soni H, Singhai AK. Synthesis, characterization and evaluation for antifungal activity of substituted diaryl imidazo [2,1-b]-benzothiazole. J Pharm Res. 2013;7:39–46. doi: 10.1016/j.jopr.2013.01.002
   Google Scholar
• Mase T, Arima H, Tomioka K, Yamada T, Murase K. Imidazo[2,1-b]benzothiazoles. 2. New immunosuppressive agents. J Med Chem. 1986:29;386–394. doi: 10.1021/jm00153a014
   PubMed Web of Science ®Google Scholar
• Trapani G, Franco M, Latrofa A, Carotti A, Genchi G, Serra M, Biggio G, Liso G. Synthesis and benzodiazepine receptor binding of some imidazo- and pyrimido[2,1-b] benzothiazoles. Eur J Med Chem. 1996;31:575–587. doi: 10.1016/0223-5234(96)89553-5
   Web of Science ®Google Scholar
• Mahesh R, Venkatesha Perumal R, Pandi PV. Microwave-assisted solvent-free synthesis of 3-[(4-substituted piperazin-1-yl)alkyl] imidazo[2,1-b][1,3]benzothiazol-2(3H)-ones as serotonin3 (5-HT3) receptor antagonists. Pharmaize. 2005;60:411–414.
   PubMed Web of Science ®Google Scholar
• Chao Q, Sprankle KG, Grotzfeld RM, Lai AG, Carter TA, Velasco AM, Gunawardane RN, Cramer MD, Gardner MF, James J, Zarrinkar PP, Patel HK, Bhagwat SS. Identification of N-(5-tert-butyl-isoxazol-3-yl)-N′-{4-[7-(2-morpholin-4-yl-ethoxy)imidazo-[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea dihydrochloride (AC220), a uniquely potent, selective, and efficacious FMS-like tyrosine kinase-3 (FLT3) inhibitor. J Med Chem. 2009;52:7808–7816. doi: 10.1021/jm9007533
   PubMed Web of Science ®Google Scholar
• El-Shorbagi A-N, Sakai S-I, El-Gendy MA, Omar N, Farag HH. Imidazo[2,1-b]benzothiazoles. I. Chem Pharm Bull. 1988;36:4760–4768. doi: 10.1248/cpb.36.4760
   Web of Science ®Google Scholar
• Pandey AK, Sharma R, Singh A, Shukla S, Srivastava K, Puri SK, Kumar B, Chauhan PMS. Synthesis of biologically active pyridoimidazole/imidazobenzothiazole annulated polyheterocycles using cyanuric chloride in water. RSC Adv. 2014;4:26757–26770. doi: 10.1039/c4ra03415e
   Web of Science ®Google Scholar
• Kumbhare RM, Kumar KV, Ramaiah MJ, Dadmal T, Pushpavalli SNCVL, Mukhopadhyay D, Divya B, Devi TA, Kosurkar U, Pal-Bhadra M. Synthesis and biological evaluation of novel Mannich bases of 2-arylimidazo[2,1-b]benzothiazoles as potential anti-cancer agents. Eur J Med Chem. 2011;46:4258–4266. doi: 10.1016/j.ejmech.2011.06.031
   PubMed Web of Science ®Google Scholar
• Amino N, Ideyama Y, Yamano M, Kuromitsu S, Tajinda K, Samizu K, Matsuhisa A, Kudoh M, Shibasaki M. YM-201627: an orally active antitumor agent with selective inhibition of vascular endothelial cell proliferation. Cancer Lett. 2006;238:119–127. doi: 10.1016/j.canlet.2005.06.037
   PubMed Web of Science ®Google Scholar
• Yousefi BH, Manook A, Drzezga A, Reutern BV, Schwaiger M, Wester H-J, Henriksen G. Synthesis and evaluation of 11C-labeled imidazo[2,1-b]benzothiazoles (IBTs) as PET tracers for imaging β-amyloid plaques in Alzheimer's disease. J Med Chem. 2011;54:949–956. doi: 10.1021/jm101129a
   PubMed Web of Science ®Google Scholar
• Chandak N, Bhardwaj JK, Sharma RK, Sharma PK. Inhibitors of apoptosis in testicular germ cells: synthesis and biological evaluation of some novel IBTs bearing sulfonamide moiety. Eur J Med Chem. 2013;59:203–208. doi: 10.1016/j.ejmech.2012.11.015
   PubMed Web of Science ®Google Scholar
• Buu-Hoi NP, Xuong ND, Cuc TT. Reaction of ω-bromoacetophenones with 2-aminothiazole and 2-aminobenzothiazoles. Bull Soc Chim France. 1966;4:1277–1279; Chem. Abstr. 1966, 65, 7164a.
   Google Scholar
• Rani R, Makrandi JK. Microwave assisted synthesis and antimicrobial activity of some 2-(benzo-furan-2-yl)-7-(substituted)imidazo[2,1-b]benzothiazoles. Indian J Chem. 2009;48B:1614–1617.
   Google Scholar
• Kovtunenko V, Potikha L, Turov A. Synthesis of fused imidazoles based on γ-bromodypnone. Synthetic Commun. 2004;34:3609–3613. doi: 10.1081/SCC-200031044
   Web of Science ®Google Scholar
• Adib M, Sheibani E, Zhu L-G, Bijanzadeh HR. Efficient synthesis of imidazo[2,1-b][1,3]benzothiazoles and 9H-imidazo-[1,2-a][1,3]benzimidazoles under solvent-free conditions. Synlett. 2008(19):2941–2944. doi: 10.1055/s-0028-1083623
   Web of Science ®Google Scholar
• Tsirulnikov S, Kysil V, Ivachtchenko A, Krasavin M. Trimethylsilyl chloride as a promoter for the Groebke-Blackburn reaction: preparation of imidazo[2,1-b][1,3]benzothiazoles. Synth Commun. 2009;40:111–119. doi: 10.1080/00397910902953331
   Web of Science ®Google Scholar
• Ogura H, Itoh T. Derivatives of imidazo[2,1-b]benzothiazole (studies on heterocyclic compounds. VII). Chem Pharm Bull. 1970;18:1981–1986. doi: 10.1248/cpb.18.1981
   Web of Science ®Google Scholar
• Landreau C, Deniaud D, Evain M, Reliquet A, Meslin J-C. Efficient regioselective synthesis of triheterocyclic compounds: imidazo[2,1-b]benzothiazoles, pyrimido[2,1-b]benzothiazolones and pyrimido[2,1-b]benzothiazoles. J Chem Soc, Perkin Trans. 2002;1:741–745. doi: 10.1039/b111639h
   Google Scholar
• Kamali TA, Habibi D, Nasrollahzadeh M. Synthesis of 6-substituted imidazo[2,1-b][1,3]thiazoles and 2-substituted imidazo[2,1-b][1,3]benzothiazoles via Pd/Cu-mediated Sonogashira coupling. Synlett. 2009(16):2601–2604.
   Web of Science ®Google Scholar
• Bakherad M, Keivanloo A, Hashemi M. One-pot synthesis of 2-substituted imidazo[2,1-b][1,3]benzothiazoles via coupling-cyclization under Pd-Cu catalysis in water. Lett in Org Chem. 2009;6:165–170. doi: 10.2174/157017809787582717
   Web of Science ®Google Scholar
• Aggarwal R, Sumran G, Singh SP, Saini A. Hypervalent iodine oxidation of benzil-α-arylimino oximes: An efficient synthesis of 2,3-diphenylquinoxaline-1-oxides. Tetrahedron Lett. 2006;47:4969–4971. doi: 10.1016/j.tetlet.2006.04.086
   Web of Science ®Google Scholar
• Aggarwal R, Kumar R, Kumar V. A facile and rapid one-pot synthesis of 1,4-diaryl-2-mercaptoimidazoles under solvent-free conditions. J Sulfur Chem. 2007;28:617–623. doi: 10.1080/17415990701625035
   Google Scholar
• Aggarwal R, Sumran G, Garg N, Aggarwal A. A regioselective synthesis of some new pyrazol-1'-ylpyrazolo[1,5-a]pyrimidines in aqueous medium and their evaluation as antimicrobial agents. Eur J Med Chem. 2011;46:3038–3046. doi: 10.1016/j.ejmech.2011.04.041
   PubMed Web of Science ®Google Scholar
• Aggarwal R, Kumar V, Bansal A, Sanz D, Claramunt RM. Multi-component solvent-free versus stepwise solvent mediated reactions: regiospecific formation of 6-trifluoromethyl and 4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines. J Fluorine Chem. 2012;140:31–37. doi: 10.1016/j.jfluchem.2012.04.007
   Web of Science ®Google Scholar
• Aggarwal R, Rani C, Sumran G. Efficient synthesis of some new 2,3-dimethylquinoxaline-1-oxides using bis(acetoxy)phenyl-λ3-iodane as an oxidant. Synth Commun. 2014;44:923–928. doi: 10.1080/00397911.2013.832775
   Web of Science ®Google Scholar
• Aggarwal R, Rani C, Sadana R, Busari K, Sharma C, Aneja KR. Hypervalent iodine mediated synthesis of some new N-(4,6-dimethylpyrimidin-2-yl)-N′-(4-arylthiazol-2-yl)hydrazines and their evaluation as antibacterial and cytotoxic agents. Chem Biol Interface. 2013;3(6):389–397.
   Google Scholar
• Aggarwal R, Kumar R. Novel and expedient regioselective synthesis of 2-imino-3-methyl-2,3-dihydrothiazoles. Synth Commun. 2008;38:2096–2102. doi: 10.1080/00397910802029356
   Web of Science ®Google Scholar
• Prakash O, Wadhwa D, Hussain K, Kumar R. [Hydroxy(tosyloxy)iodo]benzene in organic synthesis: a facile synthesis of furo[3,2-c]coumarins using α-tosyloxyketones. Synth Commun. 2012;42:2947–2951. doi: 10.1080/00397911.2011.570471
   Web of Science ®Google Scholar
• Nicolaou KC, Montagnon T, Ulven T, Baran PS, Zhong YL, Sarabia F. Novel chemistry of α-tosyloxy ketones: applications to the solution- and solid-phase synthesis of privileged heterocycle and enediyne libraries. J Am Chem Soc. 2002;124:5718–5728. doi: 10.1021/ja012146j
   PubMed Web of Science ®Google Scholar
• Stuckawisch CG. Derivatives of 2-amino-6-methoxybenzothiazole. J Am Chem Soc. 1949;71:3417–3417. doi: 10.1021/ja01178a043
   Web of Science ®Google Scholar