Ionic liquid mediated and promoted one-pot green synthesis of new isoxazolyl dihydro-1H-indol-4(5H)-one derivatives at ambient temperature

References

• Alcaide, B., Almendros, P., Aragoncillo, C., Callejo, R., Ruiz, M. P., & Torres, M. R. (2012). Diastereoselective synthesis of β-Lactam–Oxindole hybrids through a three- component reaction of azetidine-2,3-diones, α-Diazo-oxindoles, and alcohols catalyzed by [Rh2(OAc)4]. European Journal of Organic Chemistry, 12, 2359–2366.10.1002/ejoc.v2012.12
   Google Scholar
• Arya, P. J., Grewal, R. S., Kaul, C. L., Mizoni, R. H., Rajappa, S., & Shenoy, S. J. (1977). Synthesis and central nervous system depressant activity of some 2,3-disubstituted Indole. Indian Journal of Chemistry, 15B, 473–477.
   Google Scholar
• Biswal, S., Sahoo, U., Sethy, S., Kumar, H. K. S., & Banerjee, M. (2012). Indole: The molecule of diverse biological activities. Asian Journal of Pharmceutical and Clinical Research, 5, 1–6.
   Google Scholar
• Chen, Z. Y., Zheng, D. Q., & Wu, J. (2011). A facile route to polysubstituted indoles via three-component reaction of 2-ethynylaniline, sulfonyl azide, and nitroolefin. Organic Letters, 13, 848–851.10.1021/ol102775s
   Google Scholar
• Chu, C. D., Qi, Y. H., & Hao, W. (2007). A more efficient synthetic process of N- arylphthalimides in ionic liquid [bmim][BF4]. Catalysis Communications, 8, 1527–1530.
   Google Scholar
• Daidone, G., Raffa, D., Maggio, B., Plescia, F., Cutuli, V. M. C., Mangano, N. G., & Caruso, A. (1999). Synthesis and pharmacological activities of novel 3-(isoxazol-3-yl)-quinazolin-4(3h)-one derivatives. Archiv der pharmazie pharmaceutical and medicinal chemistry, 332, 50–54.10.1002/(ISSN)1521-4184
   Google Scholar
• De Greef, M. (2003). Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds. Synthesis, 10, 1471–1499.
   Google Scholar
• Dömling, A. (2006). Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chemical Reviews, 106, 17–89.10.1021/cr0505728
   Google Scholar
• Estévez, V., Villacampa, M., & Menéndez, J. C. (2010). Multi-component reactions for the synthesis of pyrroles. Chemical Society Reviews, 39, 4402–4421.10.1039/b917644f
   Google Scholar
• Fu, L. P., Shi, Q. Q., Shi, Y., Jiang, B., & Tu, S. J. (2013). Three-component domino reactions for regioselective formation of bis-indole derivatives. ACS Combinatorial Science, 15, 135–140.10.1021/co3001428
   Google Scholar
• Grasso, S., Molica, C., Monforte, A. M., Monforte, P., Zappala, M., Monforte, M. T., & Trovato, A. (1995). Synthesis and antihypertensive activity evaluation of indole derivatives n-acetamido substituted. Farmaco, 50, 113–117.
   Google Scholar
• Greaves, T. L., & Drummond, C. J. (2008). Protic ionic liquids: Properties and applications. Chemical Reviews, 108, 206–237.10.1021/cr068040u
   Google Scholar
• Haripara, K., Patel, S., Joshi, A., & Parekh, H. (2004). Synthesis and biological evaluation of some cyano pyridines and isoxazoles. Indian Journal of Heterocyclic Chemistry, 13, 221–224.
   Google Scholar
• Haumann, M., & Riisager, A. (2008). Hydroformylation in room temperature ionic liquids (rtils): Catalyst and process developments. Chemical Reviews, 108, 1474–1497.10.1021/cr078374z
   Google Scholar
• Holberg, J. D., & Seddon, K. R. (1999). The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals. Journal of the Chemical Society, Dalton Transactions, 13, 2133–2140.
   Google Scholar
• Hulme, C., & Gore, V. (2003). Multi-component reactions: Emerging chemistry in drug discovery from xylocain to crixivan. Current Medicinal Chemistry, 10, 51–80.10.2174/0929867033368600
   Google Scholar
• Jiang, B., Li, Y., Tu, M. S., Wang, S. L., Tu, S. J., & Li, G. (2012). Allylic amination and n -arylation-based domino reactions providing rapid three-component strategies to fused pyrroles with different substituted patterns. Journal of Organic Chemistry, 77, 7497–7505.10.1021/jo301323r
   Google Scholar
• Jiang, B., Yi, M. S., Shi, F., Tu, S. J., Pindi, S., McDowell, P., & Li, G. (2012). A multi- component domino reaction for the direct access to polyfunctionalized indoles via intermolecular allylic esterification and indolation. Chemical Communication, 48, 808–810.10.1039/C1CC15913E
   Google Scholar
• Joule, J. A. (2001). In E. J. Thomas (Ed.), Science of synthesis (Vol. 10, p 361). Stuttgart: Thieme.
   Google Scholar
• Kamalakar, G., Komura, K., & Sugi, Y. (2006). Tert-butylation of phenol over ordered solid acid catalysts in supercritical carbon dioxide: Efficient synthesis of 2,4-di-tert- butylphenol and 2,4,6-tri-tert-butylphenol. Industrial & Engineering Chemistry Research, 45, 6118–6126.10.1021/ie060440k
   Google Scholar
• Kumar, A., Agarwal, J. C., Nath, C., Gurtu, S., Sinha, J. N., Bhargava, K. P., & Shanker, K. (1981). Synthesis and biological activity of 2-substituted-3-ethyl-N-alkyl/arylindoles. Journal of Heterocyclic Chemistry, 18, 1269–1271.10.1002/jhet.v18:6
   Google Scholar
• Kumar, L., Bala, S., & Jeet, K. (2012). The diverse pharmacological importance of indole derivatives: A review. International Journal of Research in Pharmacy and Science, 2, 23–33.
   Google Scholar
• Li, W.-T., Hwang, D.-R., Chen, C.-P., Shen, C.-W., Huang, C.-L., Chen, T.-W., … Chen, C.-T. (2003). Synthesis and biological evaluation of N-Heterocyclic Indolyl Glyoxylamides as orally active anticancer agents. Journal of Medicinal Chemistry, 46, 1706–1715.10.1021/jm020471r
   Google Scholar
• Li, D., Shi, F., Guo, S., & Deng, Y. (2004). One-pot synthesis of silica gel confined functional ionic liquids: Effective catalysts for deoximation under mild conditions. Tetrahedron Letters, 45, 265–268.10.1016/j.tetlet.2003.10.175
   Google Scholar
• Martins, M. A. P., Frizzo, C. P., Moreira, D. N., Zanatta, N., & Bonacorso, H. G. (2008). Ionic liquids in heterocyclic synthesis. Chemical Reviews, 108, 2015–2050.10.1021/cr078399y
   Google Scholar
• Murthy, K., Rao, N. V. S., & Rao, K. S. R. K. M. (1976). Microwave-induced acetoacetylation of isoxazolyl amines with β-keto esters. Journal of Indian Chemical Society, 53, 1047–1050.
   Google Scholar
• Nagi Reddy, M., Praveen Kumar, P., & Rajanarendar, E. (2017). A fast and highly efficient one-pot synthesis of novel isoxazolylpyrido[2,3-b][1,4]oxazin-2(3H)-ones via smiles rearrangement using task-specific ionic liquid [HMIm]BF4 as green solvent. Green Chemistry Letters and Reviews, 10, 48–53.10.1080/17518253.2017.1285966
   Google Scholar
• Namboodiri, V., & Varma, R. S. (2002). Solvent-free sonochemical preparation of ionic liquids. Organic Letters, 4, 3161–3163.10.1021/ol026608p
   Google Scholar
• Panwar, H., Chaudhary, N., & Singh, S. (2011). Synthesis, characterization and biological activity of some substituted pyrazolyl and pyrazolinyl-1,3,4-thiadiazino(6,5-b)indoles. Rasayan Journal of Chemistry, 4, 371–380.
   Google Scholar
• Plaquevent, J.-C., Levillain, J., Guillen, F., Malhiac, C., & Gaumont, A.-C. (2008). Ionic liquids: New targets and media for α-amino acid and peptide chemistry. Chemical Reviews, 108, 5035–5060.10.1021/cr068218c
   Google Scholar
• Plechkova, N. V., & Seddon, K. R. (2008). Applications of ionic liquids in the chemical industry. Chemical Society Reviewes, 37, 123–150.10.1039/B006677J
   Google Scholar
• Posner, G. H. (1986). Multi-component one-pot annulations forming 3 to 6 bonds. Chemical Reviews, 86, 831–844.10.1021/cr00075a007
   Google Scholar
• Praveen Kumar, P., Rajanarendar, E., & Nagi Reddy, M. (2017). Ionic liquid [HMIm]BF4 mediated and promoted eco-friendly one-pot sequential synthesis of new isoxazolyl quinazolin-4(3H)-ones. Chemistry Select, 2, 2651–2654.
   Google Scholar
• Rajanarendar, E., Nagi Reddy, M., Govardhan Reddy, K., & Rama Krishna, S. (2012). L-Proline catalyzed efficient one-pot three-component aza-Diels–Alder reactions on nitrostyrylisoxazoles: A facile synthesis of new isoxazolyl tetrahydroquinolines and isoxazolo[2,3-a]pyrimidines. Tetrahedron Letters, 53, 2909–2913.10.1016/j.tetlet.2012.04.002
   Google Scholar
• Rajanarendar, E., Nagi Reddy, M., Murthy, K., Reddy, K., Raju, S., Srinivas, M., … Rao, M. (2010). Synthesis, antimicrobial, and mosquito larvicidal activity of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones. Bioorganic & Medicinal Chemistry Letters, 20, 6052–6055.10.1016/j.bmcl.2010.08.060
   Google Scholar
• Rajanarendar, E., Nagi Reddy, M., Rama Murthy, K., Surendar, P., Reddy, R.N., & Reddy, Y. N. (2012). Synthesis and in vitro and in vivo anticancer activity of novel phenylmethylene bis-isoxazolo[4,5-b]azepines. Bioorganic & Medicinal Chemistry Letters, 22, 149–153.10.1016/j.bmcl.2011.11.044
   Google Scholar
• Rajanarendar, E., Nagi Reddy, M., Rama Krishna, S., Rama Murthy, K., Reddy, Y. N., & Rajam, M. V. (2012). Design, synthesis, antimicrobial, anti-inflammatory and analgesic activity of novel isoxazolyl pyrimido[4,5-b]quinolines and isoxazolyl chromeno[2,3- d]pyrimidin-4-ones. European Journal of Medicinal Chemistry, 55, 273–283.10.1016/j.ejmech.2012.07.029
   Google Scholar
• Rajanarendar, E., Govrardhan Reddy, K., Sivarami Reddy, A., & Nagi Reddy, M. (2012). Brønsted acidic ionic liquid [HMIm]BF4 promoted simple and efficient one-pot green synthesis of isoxazolyl-1,3-benzoxazines at ambient temperature. Green Chemistry Letters and Reviews, 5, 699–705.
   Google Scholar
• Rajanarendar, E., Raju, S., Siva Rami Reddy, A. S., Reddy, K. G., & Nagi Redy, M. (2010). A fast and highly efficient protocol for synthesis of pyrrolo[2,3-d]isoxazoles and a new series of novel benzyl bis-pyrrolo[2,3-d]isoxazoles using task-specific ionic liquids as catalyst and green solvent. Chemical and Pharmceutical Bulletin, 58, 833–839.10.1248/cpb.58.833
   Google Scholar
• Rajanarendar, E., Raju, S., Nagi Reddy, M., Krishna, S. R., Kiran, L. H., Narasimha Reddy, A. R., Reddy, Y. N., & Reddy, Y. N. (2012). Multi-component synthesis and in vitro and in vivo anticancer activity of novel arylmethylene bis-isoxazolo[4,5-b]pyridine-N-oxides. European Journal of Medicinal Chemistry, 50, 274–279.10.1016/j.ejmech.2012.02.004
   Google Scholar
• Rajanarendar, E., Rama Murthy, K., Firoz, P. S., & Nagi Reddy, M. (2011). A fast, highly efficient and green protocol for Michael addition of activie methylene compounds to styrylisoxazoles using task-specific basic ionic liquid [bmIm]OH as catalyst and green solvent. Indian Journal of Chemistry, 50B, 587–592.
   Google Scholar
• Ranu, B. C., & Banerjee, S. (2005). Ionic liquid as catalyst and reaction medium. the dramatic influence of a task-specific ionic liquid, [bmim]oh, in michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles. Organic Letters, 7, 3049–3052.10.1021/ol051004h
   Google Scholar
• Sharma, K., & Jain, R. (2012). Synthesis, reactions and anthelmintic activity of 1-[benzimidazol-2-yl]-4-formyl-3-[2’-substituted phenyl)indole-3-yl-]pyrazoles. Indian Journal of Chemistry, 51B, 1462–1469.
   Google Scholar
• Shawkat, A. M., & Talaat, E. E. (2016). A facile one-pot synthesis of novel 1-substituted 2-(8- hydroxyquinolin-5-yl)-1,5,6,7-tetrahydro-6,6-dimethyl-4H-indol-4-one derivatives. Arkivoc, iv, 4, 184–192.
   Google Scholar
• Sheldon, R. (2001). Catalytic reactions in ionic liquids. Chemical Communications, 232399–2407.10.1039/b107270f
   Google Scholar
• Sundberg, R. J. (1996). The chemistry of indole. New York, NY: Academic.
   Google Scholar
• Talley, J. J. (1999). Selective inhibitors of cyclooxygenase-2 (COX-2). Progress in Medicinal Chemistry, 36, 201–234.10.1016/S0079-6468(08)70048-1
   Google Scholar
• Talley, J. J., Brown, D. L., Carter, J. S., Graneto, M. J., Koboldt, C. M., Masferrer, J. L., … Seibert, K. (2000). 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, valdecoxib: A potent and selective inhibitor of COX-2. Journal of Medicinal Chemistry, 43, 775–777.10.1021/jm990577v
   Google Scholar
• Tietze, L. F., & Beifuss, U. (1993). Sequential transformations in organic chemistry: A Synthetic strategy with a future. Angewandte chemie international edition in English, 32, 131–163.10.1002/(ISSN)1521-3773
   Google Scholar
• Tomita, K., Takahi, Y., Ishizuka, R., Kamamura, S., Nakagawa, M., Ando, M., … Udaira, H. (1973). Ann Sankyo Res Lab, 1, 25. Chemical Abstract, 80, 120808.
   Google Scholar
• Wang, Z. (2010). Hantzsch pyrrole synthesis. Comprehensive Organic Name Reactions and Reagents, 1326–1329. doi:10.1002/9780470638859.conrr295
   Google Scholar
• Wang, H., Cui, P., Zou, G., Yang, F., & Tang, J. (2006). Temperature-controlled highly selective dimerization of α-methylstyrene catalyzed by Brönsted acidic ionic liquid under solvent-free conditions. Tetrahedron, 62, 3985–3988.10.1016/j.tet.2006.02.025
   Google Scholar
• Weingärtner, H., & Franck, E. U. (2005). Supercritical water as a solvent. Angewandte Chemie International Edition, 44, 2672–2692.10.1002/anie.v44:18
   Google Scholar
• Wu, H.-H., Yang, F., Cui, P., Tang, J., & He, M.-Y. (2004). An efficient procedure for protection of carbonyls in Brønsted acidic ionic liquid [Hmim]BF4. Tetrahedron Letters, 45, 4963–4965.10.1016/j.tetlet.2004.04.138
   Google Scholar
• Zhu, H. P., Yang, F., Tang, J., & He, M.-Y. (2003). Brønsted acidic ionic liquid 1-methylimidazolium tetrafluoroborate: A green catalyst and recyclable medium for esterification. Green Chemistry, 5, 38–39.10.1039/b209248b
   Google Scholar