ZnS Nanoparticle Catalysed Four Component Syntheses of Novel Spiropolyhydroquinoline Derivatives in Aqueous Medium Under Ultrasonic Irradiation
Proceedings of the National Academy of Sciences, India Section A: Physical Sciences - Tập 85 - Trang 19-27 - 2014
Tóm tắt
An environmental friendly, one pot, four components ZnS nanoparticles (NPs) catalyzed synthesis of biologically important spiropolyhydroquinoline derivatives in water under ultrasonic irradiation is described. The four component reaction of substituted cyclic ketones, 5,5-dimethyl-1,3-cyclohexanedione, meldrum’s acid, and amines/ammonium acetate in which formation of multiple carbon–carbon bonds occurs in a single step does not involve any hazardous organic solvent or catalyst. The target compounds have been obtained in good yield. After the reaction, ZnS NP can be recycled and reused without any apparent loss of activity.
Tài liệu tham khảo
Ikegami S, Hamamoto H (2009) Novel recycling system for organic synthesis via designer polymer-gel catalysts. Chem Rev 109:583–593
Lu J, Toy PH (2009) Organic polymer supports for synthesis and for reagent and catalyst immobilization. Chem Rev 109:815–838
Scheuermann GM, Rumi L, Steurer P, Bannwarth W, Mulhaupt R (2009) Palladium nanoparticles on graphite oxide and its functionalized graphene derivatives as highly active catalysts for the suzuki–miyaura coupling reaction. J Am Chem Soc 131:8262–8270
Shiju NR, Guliants VV (2009) Recent developments in catalysis using nanostructured materials. Appl Catal A Gen 356:1–17
Pachon LD, Rothenberg G (2008) Transition-metal nanoparticles: synthesis, stability and the leaching issue. Appl Organomet Chem 22:288–299
Borm PJA, Kreyling W (2004) Toxicological hazards of inhaled nanoparticles potential implications for drug delivery. Nanosci Nanotechnol 4:1–11
Hosseini-Sarvari M, Etemad S (2008) Nanosized zinc oxide as a catalyst for the rapid and green synthesis of β-phosphono malonates. Tetrahedron 64:5519–5523
Hosseini-Sarvari M, Sharghi H, Etemad S (2008) Nanocrystalline ZnO for Knoevenagel condensation and reduction of the carbon-carbon double bond in conjugated alkenes. Helv Chim Acta 91:715–724
Mirjafary Z, Saeidian H, Sadeghi A, Matloubi MF (2008) ZnO nanoparticles: an efficient nanocatalyst for the synthesis of β-acetamido ketones/esters via a multi-component reaction. Catal Commun 9:299–306
Jiang B, Li-Y Xue, Wang X-H, Tu M-S, Liu Y-P, Tu S-J (2012) Microwave-assisted multicomponent reaction of aryl amidines: regiospecific synthesis of new polysubstituted thiopyrano-, and pyrano[4,3-d]pyrimidines. Tetrahedron Lett 53:1261–1264
Zhu J, Bienayme H (2005) Multicomponent reactions. In: Zhu J, Bienayme H (eds) WILEY-VCH Verlag GmbH & Co: KGaA, Weinheim and references cited therein
Nuchter M, Ondruschka B, Jungnickel A, Muller U (2000) Organic processes initiated by non-classical energy sources. J Phys Org Chem 13:579–586
Varma RS (2008) Chemical activation by mechanochemical mixing, microwave and ultrasonic irradiation. Green Chem 10:1129–1130 and references cited therein
Mason TJ, Lorimer JP (1987) Sonochemistry part 1—the physical aspects. Chem Soc Rev 16:239–274
Li JT, Wang SX, Chen GF, Li TS (2005) Some applications of ultrasound irradiation in organic synthesis. Curr Org Synth 2:415–436
Cravotto G, Cintas P (2006) Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications. Chem Soc Rev 35:180–196
Mason TJ, Cintas P (2002) Handbook of green chemistry and technology. In: Clark J, Macquarrie D (eds) Blackwell Science, Oxford, p 372
Demko ZP, Sharpless KB (2001) Preparation of 5-substituted 1H-tetrazoles from nitriles in water. J Org Chem 66:7945–7950
Li C-J (2005) Organic reactions in aqueous media with a focus on carbon–carbon bond formations: a decade update. Chem Rev 105:3095–3166
Azizi N, Aryanasab F, Torkiyan L, Ziyaei A, Saidi MR (2006) One-pot synthesis of dithiocarbamates accelerated in water. J Org Chem 71:3634–3635
Herrerias CI, Yao X, Li Z, Li C (2007) Reactions of C–H bonds in water. Chem Rev 107:2546–2562
James DM, Kunze HB, Faulkner DJ (1991) Two new brominated tyrosine derivatives from the sponge Druinella (=Psammaplysilla) purpurea. J Nat Prod 54:1137–1140
Pradhan R, Patra M, Behera AK, Mishra BK, Behera RKA (2006) Synthon approach to spiro compounds. Tetrahedron 62:779–828
Dandia A, Parewa V, Jain AK, Rathore KS (2011) Step-economic, efficient, ZnS nanoparticle-catalyzed synthesis of spirooxindole derivatives in aqueous medium via Knoevenagel condensation followed by Michael addition. Green Chem 13:2135–2145
Dandia A, Parewa V, Rathore KS (2012) Synthesis and characterization of CdS and Mn doped CdS nanoparticles and their catalytic application for chemoselective synthesis of benzimidazoles and benzothiazoles in aqueous medium. Catal Commun 28:90–94
Dandia A, Singh R, Bhaskaran S (2011) Versatile three component procedure for combinatorial synthesis of biologically relevant scaffold spiro[indole-thiazolidinones] under aqueous conditions. Green Chem 13:1852–1859
Dandia A, Singh R, Bhaskaran S (2011) Facile stereoslective synthesis of spiro[indole-oxiranes] by combination of phase transfer catalyst and ultrasound irradiation and their bioassay. Ultrason Sonochem 18:1113–1117
Dandia A, Sati M, Arya K, Loupy A (2002) Dry-media one-pot syntheses of fluorinated-2,3-dihydro-1,5-benzothiazepines under microwave activation. Green Chem 4:599–602
Bausch J, Fasano CG, Gostowski R, Selmarten D, Vaughn A (1991) Relative homolytic strengths of carbon-hydrogen bonds in meldrum’s acid and dimethyl malonate. J Org Chem 56:5640–5642
Mason TJ (1997) Ultrasound in synthetic organic chemistry. Chem Soc Rev 26:443–451
Price GJ (1992) Current trends in sonochemistry. In: Price GJ (ed) Royal Society of Chemistry, Cambridge, p 87
Cravotto G, Gaudinoa EC, Cintas P (2013) On the mechanochemical activation by ultrasound. Chem Soc Rev 42:7521–7534