Abstract
An innovative, powerful, efficient and relatively rapid method was developed to synthesise various β-aminoketone derivatives from cyclohexanone, substituted aromatic amines and aromatic or hetero-aromatic aldehydes via ultrasound-assisted direct-type catalytic Mannich reaction using bismuth(III) triflate in water. Good yields of the desired β-aminoketones were obtained at room temperature by ultrasound-assisted reaction within 1–2 h. The major advantages of the proposed method are undemanding conditions, easy operation, low toxicity, shorter reaction time, anti selectivity and higher yields in comparison with conventional methods.
[1] Ando, T., Kimura, T., Fujita, M., Levęque, J. M., & Luche, J. L. (2001). Scavenging of the radical species formed in the sonochemical excitation of styrenes. Tetrahedron Letters, 42, 6865–6867. DOI: 10.1016/S0040-4039(01)01395-8. http://dx.doi.org/10.1016/S0040-4039(01)01395-810.1016/S0040-4039(01)01395-8Search in Google Scholar
[2] Bhadra, S., Saha, A., & Ranu, B. C. (2008). One-pot copper nanoparticle-catalyzed synthesis of S-aryl- and S-vinyl dithiocarbamates in water: high diastereoselectivity achieved for vinyl dithiocarbamates. Green Chemistry, 10, 1224–1230. DOI: 10.1039/B809200A. http://dx.doi.org/10.1039/b809200a10.1039/b809200aSearch in Google Scholar
[3] Cabello, N., Cintas, P., & Luche, J. L. (2003). Sonochemical effects in the additions of furan to masked orthobenzoquinones. Ultrasonics Sonochemistry, 10, 25–31. DOI: 10.1016/S1350-4177(02)00103-7. http://dx.doi.org/10.1016/S1350-4177(02)00103-710.1016/S1350-4177(02)00103-7Search in Google Scholar
[4] Chen, W. Y., & Li, X. S. (2009). The solvent-free vinylogous Mannich reaction of dicyanoalkylidenes with α-amido sulfones under ultrasound irradiation. Catalysis Communications, 10, 549–551. DOI: 10.1016/j.catcom.2008.10.031. http://dx.doi.org/10.1016/j.catcom.2008.10.03110.1016/j.catcom.2008.10.031Search in Google Scholar
[5] Dubs, C., Hamashima, Y., Sasamoto, N., Seidel, T. M., Suzuki, S., Hashizume, D., & Sodeoka, M. (2008). Mechanistic studies on the catalytic asymmetric Mannich-type reaction with dihydroisoquinolines and development of oxidative Mannich-type reactions starting from tetrahydroisoquinolines. The Journal of Organic Chemistry, 73, 5859–5871. DOI: 10.1021/jo800800y. http://dx.doi.org/10.1021/jo800800y10.1021/jo800800ySearch in Google Scholar PubMed
[6] Eftekhari-Sis, B., Abdollahifar, A., Hashemi, M. M., & Zirak, M. (2006). Stereoselective synthesis of β-amino ketones via directMannich-type reactions, catalyzed with ZrOCl2 · 8H2O under solvent-free conditions. European Journal of Organic Chemistry, 2006, 5152–5157. DOI: 10.1002/ejoc.200600493. http://dx.doi.org/10.1002/ejoc.20060049310.1002/ejoc.200600493Search in Google Scholar
[7] Hong, D., Yang, Y. Y., Wang, Y. G., & Lin, X. F. (2009). A Yb(OTf)3/PEG-supported quaternary ammonium salt catalyst system for a three-component Mannich-type reaction in aqueous media. Synlett, 2009, 1107–1110. DOI: 10.1055/s-0028-1088221. http://dx.doi.org/10.1055/s-0028-108822110.1055/s-0028-1088221Search in Google Scholar
[8] Hota, S. K., Chatterjee, A., Bhattacharya, P. K., & Chattopadhyay, P. (2009). A green chemical approach for the Nalkylation of aldoximes to form nitrones in organized aqueous media and their in situ cycloaddition with olefins. Green Chemistry, 11, 169–176. DOI: 10.1039/B812290C. http://dx.doi.org/10.1039/b812290c10.1039/B812290CSearch in Google Scholar
[9] Josephsohn, N. S., Carswell, E. L., Snapper, M. L., & Hoveyda, A. H. (2005). Practical and highly enantioselective synthesis of β-alkynyl-β-amino esters through Agcatalyzed asymmetric Mannich reactions of silylketene acetals and alkynyl imines. Organic Letters, 7, 2711–2713. DOI: 10.1021/ol050910r. http://dx.doi.org/10.1021/ol050910r10.1021/ol050910rSearch in Google Scholar PubMed PubMed Central
[10] Kantam, M. L., Rajasekhar C. V., Gopikrishna, G., Reddy, K. R., & Choudary, B. M. (2006). Proline catalyzed two-component, three-component and self-asymmetric Mannich reactions promoted by ultrasonic conditions. Tetrahedron Letters, 47, 5965–5967. DOI: 10.1016/j.tetlet.2006.06.042. http://dx.doi.org/10.1016/j.tetlet.2006.06.04210.1016/j.tetlet.2006.06.042Search in Google Scholar
[11] Kobayashi, S., Araki, M., & Yasuda, M. (1995). One-pot synthesis of β-amino esters from aldehydes using lanthanide triflate as a catalyst. Tetrahedron Letters, 36, 5773–5776. DOI: 10.1016/0040-4039(95)01096-Z. 10.1016/0040-4039(95)01096-ZSearch in Google Scholar
[12] Kobayashi, S., Busujima, T., & Nagayama, S. (1999b). Ln(OTf)3- or Cu(OTf)2-catalyzed Mannich-type reactions of aldehydes, amines, and silyl enolates in micellar systems. Facile synthesis of β-amino ketones and esters in water. Synlett, 1999, 545–546. DOI: 10.1055/s-1999-2693. 10.1055/s-1999-2693Search in Google Scholar
[13] Kobayashi, S., Hamada, T., & Manabe, K. (2002). The catalytic asymmetric Mannich-type reactions in aqueous media. Journal of the American Chemical Society, 124, 5640–5641. DOI: 10.1021/ja026094p. http://dx.doi.org/10.1021/ja026094p10.1021/ja026094pSearch in Google Scholar
[14] Kobayashi, S., & Ishitani, H. (1999a). Catalytic enantioselective addition to imines. Chemical Reviews, 99, 1069–1094. DOI: 10.1021/cr980414z. http://dx.doi.org/10.1021/cr980414z10.1021/cr980414zSearch in Google Scholar
[15] Kobayashi, S., Moriwaki, M., Akiyama, R., Suzuki, S., & Hachiya, I. (1996). Parallel synthesis using Mannich-type three-component reactions and “field synthesis” for the construction of an amino alcohol library. Tetrahedron Letters, 37, 7783–7786. DOI: 10.1016/0040-4039(96)01777-7. http://dx.doi.org/10.1016/0040-4039(96)01777-710.1016/0040-4039(96)01777-7Search in Google Scholar
[16] Kumar, V., Sharma, A., Sharma, M., Sharma, U. K., & Sinha, A. K. (2007). DDQ catalyzed benzylic acetoxylation of arylalkanes: a case of exquisitely controlled oxidation under sonochemical activation. Tetrahedron, 63, 9718–9723. DOI: 10.1016/j.tet.2007.07.018. http://dx.doi.org/10.1016/j.tet.2007.07.01810.1016/j.tet.2007.07.018Search in Google Scholar
[17] Kureshy, R. I., Agrawal, S., Saravanan, S., Khan, N. H., Shah, A. P, Abdi, S. H. R., Bajaj, H. C., & Suresh, E. (2010). Direct Mannich reaction mediated by Fe(Cp)2PF6 under solvent-free conditions. Tetrahedron Letters, 51, 489–494. DOI: 10.1016/j.tetlet.2009.11.022. http://dx.doi.org/10.1016/j.tetlet.2009.11.02210.1016/j.tetlet.2009.11.022Search in Google Scholar
[18] Li, C. J., & Chan, T. H. (2007). Compherensive organic reactions in aqueous media (2nd ed.). Hoboken, NJ, USA: Wiley. http://dx.doi.org/10.1002/978047013144210.1002/9780470131442Search in Google Scholar
[19] List, B., Pojarliev, P., Biller, W. T., & Martin, H. J. (2002). The proline-catalyzed direct asymmetric three-component Mannich reaction: scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols. Journal of the American Chemical Society, 124, 827–833. DOI: 10.1021/ja0174231. http://dx.doi.org/10.1021/ja017423110.1021/ja0174231Search in Google Scholar PubMed
[20] Liu, Y. Q., Li, L. H., Yang, L., & Li, H. Y. (2010). A novel, stereoselective and practical protocol for the synthesis of 4β-aminopodophyllotoxins. Chemical Papers, 64, 533–536. DOI: 10.2478/s11696-010-0020-z. http://dx.doi.org/10.2478/s11696-010-0020-z10.2478/s11696-010-0020-zSearch in Google Scholar
[21] Luche, J. L. (1997). A few questions on the sonochemistry of solutions. Ultrasonics Sonochemistry, 4, 211–215. DOI: 10.1016/S1350-4177(97)00008-4. http://dx.doi.org/10.1016/S1350-4177(97)00008-410.1016/S1350-4177(97)00008-4Search in Google Scholar
[22] Manabe, K., Mori, Y., & Kobayashi, S. (2001). Three-component carbon-carbon bond-forming reactions catalyzed by a Brønsted acid-surfactant-combined catalyst in water. Tetrahedron, 57, 2537–2544. DOI: 10.1016/S0040-4020(01)00081-3. http://dx.doi.org/10.1016/S0040-4020(01)00081-310.1016/S0040-4020(01)00081-3Search in Google Scholar
[23] Mečiarovč, M., Poláčková V., & Toma, Š. (2002). The effect of microwave and ultrasonic irradiation on the reactivity of benzaldehydes under Al2O3, Ba(OH)2, and K2CO3 catalysis. Chemical Papers, 56, 208–213. Search in Google Scholar
[24] Mečiarová M., Toma, Š., & Babiak, P. (2004). Effect of ultrasound on one-pot conversion of alcohols to nitro and azido compounds. Chemical Papers, 58, 104–108. Search in Google Scholar
[25] Meciarova, M., Toma, S., & Luche, J. L. (2001). The sonochemical arylation of malonic esters mediated by manganese triacetate. Ultrasonics Sonochemistry, 8, 119–122. DOI: 10.1016/S1350-4177(00)00029-8. http://dx.doi.org/10.1016/S1350-4177(00)00029-810.1016/S1350-4177(00)00029-8Search in Google Scholar
[26] Mhaske, S. B., & Argade, N. P. (2006). The chemistry of recently isolated naturally occurring quinazolinone alkaloids. Tetrahedron, 62, 9787–9826. DOI: 10.1016/j.tet.2006.07.098. http://dx.doi.org/10.1016/j.tet.2006.07.09810.1016/j.tet.2006.07.098Search in Google Scholar
[27] Noei, J., & Khosropour, A. R. (2009). Ultrasound-promoted a green protocol for the synthesis of 2,4-diarylthiazoles under ambient temperature in [bmim]BF4. Ultrasonics Sonochemistry, 16, 711–717. DOI: 10.1016/j.ultsonch.2009.04.001. http://dx.doi.org/10.1016/j.ultsonch.2009.04.00110.1016/j.ultsonch.2009.04.001Search in Google Scholar PubMed
[28] Ollevier, T., Desyroy, V., & Nadeau, E. (2007). Recent advances in bismuth mediated aldol and Mannich reactions. ARKIVOC, 2007(x), 10–20. Search in Google Scholar
[29] Ollevier, T., & Nadeau, E. (2004). Bismuth triflate-catalyzed three-component Mannich-type reaction. The Journal of Organic Chemistry, 69, 9292–9295. DOI: 10.1021/jo048617c. http://dx.doi.org/10.1021/jo048617c10.1021/jo048617cSearch in Google Scholar PubMed
[30] Ollevier, T., & Nadeau, E. (2007). An efficient and mild bismuth triflate-catalyzed three-component Mannich-type reaction. Organic & Biomolecular Chemistry, 5, 3126–3134. DOI: 10.1039/b710794c. http://dx.doi.org/10.1039/b710794c10.1039/b710794cSearch in Google Scholar PubMed
[31] Ollevier, T., Nadeau, E., & Eguillon, J. C. (2006a). The first catalytic Mannich-type reaction of N-alkoxycarbonylamino sulfones with silyl enolates. Advanced Synthesis & Catalysis, 348, 2080–2084. DOI: 10.1002/adsc.200606222. http://dx.doi.org/10.1002/adsc.20060622210.1002/adsc.200606222Search in Google Scholar
[32] Ollevier, T., Nadeau, E., & Guay-Bégin, A. A. (2006b). Direct-type catalytic three-component Mannich reaction in aqueous media. Tetrahedron Letters, 47, 8351–8354. DOI: 10.1016/j.tetlet.2006.09.082. http://dx.doi.org/10.1016/j.tetlet.2006.09.08210.1016/j.tetlet.2006.09.082Search in Google Scholar
[33] Sinha, A. K., Sharma, A., & Joshi, B. P. (2007). One-pot twostep synthesis of 4-vinylphenols from 4-hydroxy substituted benzaldehydes under microwave irradiation: a new perspective on the classical Knoevenagel-Doebner reaction. Tetrahedron, 63, 960–965. DOI: 10.1016/j.tet.2006.11.023. http://dx.doi.org/10.1016/j.tet.2006.11.02310.1016/j.tet.2006.11.023Search in Google Scholar
[34] Tabatabaeian, K., Mamaghani, M., Mahmoodi, N. O., & Khorshidi, A. (2008). Ultrasonic-assisted ruthenium-catalyzed oxidation of aromatic and heteroaromatic compounds. Catalysis Communications, 9, 416–420. DOI: 10.1016/j.catcom.2007.07.024. http://dx.doi.org/10.1016/j.catcom.2007.07.02410.1016/j.catcom.2007.07.024Search in Google Scholar
[35] Trost, B. M., & Terrell, L. R. (2003). A direct catalytic asymmetric Mannich-type reaction to syn-amino alcohols. Journal of the American Chemical Society, 125, 338–339. DOI: 10.1021/ja028782e. http://dx.doi.org/10.1021/ja028782e10.1021/ja028782eSearch in Google Scholar
[36] Ueno, M., & Kobayashi, S. (2005). Catalytic enantioselective Mannich reactions. In E. Juaristi, & V. Soloshonok (Eds.), Enantioselective synthesis of β-amino acids (2nd ed., pp. 139–158). Hoboken, NJ, USA: Wiley. http://dx.doi.org/10.1002/0471698482.ch610.1002/0471698482.ch6Search in Google Scholar
[37] Vinatoru, M., Bartha, E., Badea, F., & Luche, J. L. (1998). Sonochemical and thermal redox reactions of triphenylmethane and triphenylmethyl carbinol in nitrobenzene. Ultrasonics Sonochemistry, 5, 27–31. DOI: 10.1016/S1350-4177(98)00004-2. http://dx.doi.org/10.1016/S1350-4177(98)00004-210.1016/S1350-4177(98)00004-2Search in Google Scholar
[38] Wei, H. L., Yan, Z. Y., Niu, Y. N., Li, G. Q., & Liang, Y. M. (2007). New light on an old story: facile and efficient synthesis of 1,3-diaryl-5-spirohexahydropyridimines via a six-molecule, three-component Mannich-type reaction. The Journal of Organic Chemistry, 72, 8600–8603. DOI: 10.1021/jo7016235. http://dx.doi.org/10.1021/jo701623510.1021/jo7016235Search in Google Scholar PubMed
[39] Wu, Y. S., Cai, J., Hu, Z. Y., & Lin, G. X. (2004). A new class of metal-free catalysts for direct diastereo- and regioselective Mannich reactions in aqueous media. Tetrahedron Letters, 45, 8949–8952. DOI: 10.1016/j.tetlet.2004.09.174. http://dx.doi.org/10.1016/j.tetlet.2004.09.17410.1016/j.tetlet.2004.09.174Search in Google Scholar
[40] Xia, M., & Lu, Y. D. (2007). Ultrasound-assisted one-pot approach to α-amino phosphonates under solvent-free and catalyst-free conditions. Ultrasonics Sonochemistry, 14, 235–240. DOI: 10.1016/j.ultsonch.2006.04.006. http://dx.doi.org/10.1016/j.ultsonch.2006.04.00610.1016/j.ultsonch.2006.04.006Search in Google Scholar PubMed
[41] Xu, H., Liao, W. M., & Li, H. F. (2007). A mild and efficient ultrasound-assisted synthesis of diaryl ethers without any catalyst. Ultrasonics Sonochemistry, 14, 779–782. DOI: 10.1016/j.ultsonch.2007.01.002. http://dx.doi.org/10.1016/j.ultsonch.2007.01.00210.1016/j.ultsonch.2007.01.002Search in Google Scholar PubMed
© 2011 Institute of Chemistry, Slovak Academy of Sciences
