CuI-nanoparticles-catalyzed one-pot synthesis of benzo[b]furans via three-component coupling of aldehydes, amines and alkyne

Journal of Saudi Chemical Society

Volumn 20, Issue 5, 2016, Pages 502-509

  Safaei Ghomi, Javad ^a   Ghasemzadeh, Mohammad Ali ^a   Kakavand Qalenoei, Ahmad ^a  

^a UNIVERSITY OF KASHAN   (Iran)

Author keywords

Benzofuran; CuI nanoparticles; Heterogeneous catalyst; Multi component reactions; One pot

Indexed keywords

EID: 84866680476     PISSN: 13196103     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jscs.2012.07.010     Document Type: Article

References (40)

1. Astruc, D., Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon–carbon coupling precatalysts: a unifying view. Inorg. Chem. 46:6 (2007), 1884–1894.
2. Baraldi, P.G., Romagnoli, R., Beria, I., Cozzi, P., Geroni, C., Mongelli, N., Bianchi, N., Mischiati, C., Gambari, R., Synthesis and antitumor activity of new benzoheterocyclic derivatives of distamycin A. J. Med. Chem. 43:14 (2000), 2675–2684.
3. Beck, K.D., Moore, L.B., Kliewer, S.A., Lehmann, J.M., The structure−activity relationship between peroxisome proliferator-activated receptor γ agonism and the antihyperglycemic activity of thiazolidinediones. J. Med. Chem. 39:3 (1995), 665–668.
4. Benkli, K., Gundogdu-Karaburun, N., Karaburun, A.C., Ucucu, U., Demirayak, S., Kiraz, N., Synthesis and antifungal activities of some aryl (3-methyl-benzofuran-2-yl) ketoximes. Arch. Pharm. Res. 26:3 (2003), 202–206.
5. Bing, Z., Scott, H., Raja, R., Gabor, A., Nanotechnology in Catalysis. 2007, Springer, Ottawa.
6. Bird, C.W., Cheeseman, G.W.H., Comprehensive Heterocyclic Chemistry, vol. 4, 1984, Pergamon Press, Oxford, 89.
7. Black, D.A., Arndtsen, A., Copper-catalyzed coupling of imines, acid chlorides, and alkynes: a multicomponent route to propargylamides. Org. Lett. 6:7 (2004), 1107–1110.
8. Buu-Hoi, N., Saint-Ruf, G., Loc, T.B., Xuong, N.D., Aroylbenzofurans, aroyldibenzofurans, and aroylcoumarins of potential biological interest. J. Chem. Soc., 1957, 2593–2596.
9. Cassidy, M.P., Raushel, J., Fokin, V.V., Practical synthesis of amides from in situ generated copper(i) acetylides and sulfonyl azides. Angew. Chem. Int. Ed. 45:19 (2006), 3154–3157.
10. Dai, W.M., Lai, K.W., Chemistry of aminophenols. Part 3: First synthesis of nitrobenzo[b]furans via a coupling-cyclization approach. Tetrahedron Lett. 43:51 (2002), 9377–9380.
11. Edward, A.K., Anton, L.M., Yulia, S.K., Vitaliy, A.S., Sergey, V., Copper nanoparticles as active catalysts in hydroxylation of phenol by hydrogen peroxide. Appl. Catal. A 385:1–2 (2010), 62–72.
12. Elvers, B., Hawkins, S., Schulz, G., Ulmann's Encyclopedia of Industrial Chemistry, Optical Brighteners. vol. A18, fifth ed., 1999, VCH, Weinheim p. 153.
13. Hennings, D.D., Iwasa, S., Rawal, V.H., Anion-accelerated palladium-mediated intramolecular cyclizations: synthesis of benzofurans, indoles, and a benzopyran. Tetrahedron Lett. 38:36 (1997), 6379–6382.
14. Hongfeng, L., Jun, L., Bin, Ya., Yanzhong, L., New domino approach for the synthesis of 2,3-disubstituted benzo[b]furans via copper-catalyzed multi-component coupling reactions followed by cyclization. Tetrahedron Lett. 50:20 (2009), 2353–2357.
15. Hua-Jian, X., Liang, Y., Cai, Z., Qi, H., Yang, C., Feng, Y., CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides in aqueous solution. J. Org. Chem. 76:7 (2011), 2296–2300.
16. Kamijo, S., Jin, T., Huo, Z., Yamamoto, Y., A one-pot procedure for the regiocontrolled synthesis of allyltriazoles via the Pd–Cu bimetallic catalyzed three-component coupling reaction of non activated terminal alkynes, allyl carbonate, and trimethylsilyl azide. J. Org. Chem. 69:7 (2004), 2386–2393.
17. Kantam, M.L., Jaya, V.S., Sreedhar, B., Rao, M.M., Choudary, B.M., Preparation of alumina supported copper nanoparticles and their application in the synthesis of 1,2,3-triazoles. J. Mol. Catal. A: Chem. 256:1 (2006), 273–277.
18. Kantam, M.L., Laha, S., Yadav, J., Bhargav, S., An efficient synthesis of propargylamines via three-component coupling of aldehydes, amines and alkynes catalyzed by nanocrystalline copper(II) oxide. Tetrahedron Lett. 49:19 (2008), 3083–3086.
19. Kidwai, M., Mishra, N.K., Bansal, V., Kumar, A., Mozumdar, S., Novel one-pot Cu-nanoparticles-catalyzed Mannich reaction. Tetrahedron Lett. 50:12 (2009), 1355–1358.
20. Leung, A.Y., Foster, S., Encyclopedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics. 1996, Wiley, New York.
21. Li, C.J., Chan, T.-H., Organic Reactions in Aqueous Media. 1997, John Wiley & Sons, New York.
22. Li, J., Rush, T.S., Vincentis, D., Skotnicki, J.S., Tam, S., Cunningham, K.M., Synthesis and SAR of highly selective MMP-13 inhibitors. Bioorg. Med. Chem. Lett. 15:22 (2005), 4961–4966.
23. Lu, L., Sui, M.L., Lu, K., Superplastic extensibility of nanocrystalline copper at room temperature. Science 287:5457 (2000), 1463–1466.
24. Min, Y., Akbulut, M., Kristiansen, K., Golan, Y., Israelachvili, J., The role of interparticle and external forces in nanoparticle assembly. Nat. Mater. 7:7 (2008), 527–538.
25. Negwar, M., Organic-Chemical Drugs and their Synonyms, seventh ed., 1994, Akademie, Berlin.
26. Rideout, D.C., Breslow, R.L., Hydrophobic acceleration of Diels–Alder reactions. J. Am. Chem. Soc. 102:26 (1980), 7816–7817.
27. Rout, L., Jammi, S., Punniyamurthy, T., Novel CuO nanoparticle catalyzed C−N cross coupling of amines with iodobenzene. Org. Lett. 9:17 (2007), 3397–3399.
28. Safaei-Ghomi, J., Ghasemzadeh, M.A., An efficient multi-component synthesis of 14-aryl-14H-dibenzo[a, j]xanthene derivatives by AgI nanoparticles. J. Saudi Chem. Soc. 19:6 (2015), 642–649.
29. Safaei-Ghomi, J., Kakavand-Qalenoei, A., Ghasemzadeh, M.A., Salavati-Niasari, M., 2012. Efficient one-pot alkylation of imines using nanosilver iodide in aqueous media. Turk. J. Chem. http://dx.doi.org/10.3906/kim-1201-40.
30. Sakai, N., Uchida, N., Konakahara, T., Facile and efficient synthesis of polyfunctionalized benzofurans: three-component coupling reactions from an alkynyl silane, an o-hydroxy benzaldehyde derivative, and a secondary amine by a Cu(I)–Cu(II) cooperative catalytic system. Tetrahedron Lett. 49:21 (2008), 3437–3440.
31. Sheradsky, T., Application of the Fischer indole synthesis to the preparation of benzofurans. Tetrahedron Lett. 7:43 (1966), 5225–5227.
32. Simpson, T.J., Thomson, R.H., The Chemistry of Natural Products. 1985, Blackie, London.
33. Song, Y., Yoo, C., Hong, J.T., Kim, S.J., Jang, H.Y., Nanocrystalline copper oxide (II)-catalyzed alkyne-azide cycloadditions. Bull. Korean Chem. Soc. 29 (2008), 1561–1564.
34. Suribabu, J., Sekarpandi, S., Laxmidhar, R., Tathagata, M., Santu, M., Raja, M., Prasenjit, S., Punniyamurthy, T., CuO nanoparticles catalyzed C−N, C−O, and C−S cross-coupling reactions: scope and mechanism. J. Org. Chem. 74:5 (2009), 1971–1976.
35. Thielges, S., Meddah, E., Bisseret, P., Eustache, J., New synthesis of benzo[b]furan and indole derivatives from 1,1-dibromo-1-alkenes using a tandem Pd-assisted cyclization-coupling reaction. Tetrahedron Lett. 45:5 (2004), 907–910.
36. Thompson, L.A., Ellman, J.A., Synthesis and applications of small molecule libraries. Chem. Rev. 96:1 (1996), 555–600.
37. Wright, J.B., Some reactions of mannich bases derived from α-phenoxyacetophenone and α-phenoxypropiophenone. J. Org. Chem. 25:11 (1960), 1867–1872.
38. Yadav, J.S., Swami, T., Reddy, B.V.S., Krishna, R.D., Organic synthesis in water: green protocol for the conjugate addition of thiols to p-quinones. J. Mol. Catal. A: Chem. 274:1 (2007), 116–119.
39. Yang, Y., Liu, S., Kimura, K., Synthesis of well-dispersed CuI nanoparticles from an available solution precursor. Chem. Lett. 34:8 (2005), 1158–1159.
40. Yu, D., Zhang, Yugen., Copper-catalyzed three-component coupling of terminal alkyne, dihalomethane and amine to propargylic amines. Adv. Synth. Catal. 353:1 (2010), 163–169.