Environmentally benign one-pot synthesis and antimicrobial activity of 1-methyl-2,6-diarylpiperidin-4-ones

[1] Aridoss, G., Parthiban, P., Ramachandran, R., Prakash, M., Kabilan, S., & Jeong, Y. T. (2009). Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: Antimicrobial, analgesic and antipyretic studies. European Journal of Medicinal Chemistry, 44, 577–592. DOI: 10.1016/j.ejmech.2008.03.031. http://dx.doi.org/10.1016/j.ejmech.2008.03.03110.1016/j.ejmech.2008.03.031Search in Google Scholar

[2] Balasubramanian, M., & D’souza, A. (1963). Preparation and configuration of some cyclohexanols. Tetrahedron Letters, 4, 1891–1895. DOI: 10.1016/S0040-4039(01)90936-0. http://dx.doi.org/10.1016/S0040-4039(01)90936-010.1016/S0040-4039(01)90936-0Search in Google Scholar

[3] Balasubramanian, M., & Padma, N. (1968). Catalytic reduction of some 4-piperidones. Tetrahedron, 24, 5395–5398. DOI: 10.1016/S0040-4020(01)96333-1. http://dx.doi.org/10.1016/S0040-4020(01)96333-110.1016/S0040-4020(01)96333-1Search in Google Scholar

[4] Balasubramanian, M., & Padma, N. (1963a). Boat-chair equilibrium in a 4-piperidinol. Tetrahedron Letters, 4, 49–52. DOI: 10.1016/S0040-4039(01)90575-1. http://dx.doi.org/10.1016/S0040-4039(01)90575-110.1016/S0040-4039(01)90575-1Search in Google Scholar

[5] Balasubramanian, M. B., & Padma, N. (1963b). Studies on conformation—I: Preparation and stereochemistry of some 4-piperidinols. Tetrahedron, 19, 2135–2143. DOI: 10.1016/0040-4020(63)85028-0. http://dx.doi.org/10.1016/0040-4020(63)85028-010.1016/0040-4020(63)85028-0Search in Google Scholar

[6] Baliah, V., & Gopalakrishnan, V. (1954). Synthesis of some 4-piperidone derivatives. Journal of the Indian Chemical Society, 31, 250–252. Search in Google Scholar

[7] Baliah, V., Jeyaraman, R., & Chandrasekaran, L. (1983). Synthesis of 2,6-disubstituted piperidines, oxanes, and thianes. Chemical Reviews, 83, 379–423. DOI: 10.1021/cr00056a002. http://dx.doi.org/10.1021/cr00056a00210.1021/cr00056a002Search in Google Scholar

[8] Barry, A L. (1976). The antimicrobial susceptibility test: Principles and practices. Philadelphia, PA, USA: Lea & Febiger. Search in Google Scholar

[9] Dasgupta, S., & Török, B. (2008). Application of clay catalysts in organic synthesis. A review. Organic Preparations and Procedures International: The New Journal for Organic Synthesis, 40, 1–65 DOI: 10.1080/00304940809356640. http://dx.doi.org/10.1080/0030494080935664010.1080/00304940809356640Search in Google Scholar

[10] Dhar, M. L., Dhar, M. M., Dhawan, B. N., Mehrotra, B. N., & Ray, C. (1968). Screening of Indian plants for biological activity: I. Indian Journal of Experimental Biology, 6, 232–247. Search in Google Scholar

[11] Dimmock, J. R., Arora, V. K., Quail, J. W., Pugazhenthi, U., Allen, T. M., Kao, G. Y., & De Clercq, E. (1994). Cytotoxic evaluation of some 3,5-diarylidene-4-piperidones and various related quaternary ammonium compounds and analogs. Journal of Pharmaceutical Sciences, 83, 1124–1130. DOI: 10.1002/jps.2600830811. http://dx.doi.org/10.1002/jps.260083081110.1002/jps.2600830811Search in Google Scholar PubMed

[12] Edwards, M. W., Daly, J. W., & Myers, C. W. (1988). Alkaloids from a Panamanian poison frog, dendrobates speciosus: Identification of pumiliotoxin-A and allo-pumiliotoxin class alkaloids, 3,5-disubstituted dndolizidines, 5-substituted 8-methylindolizidines, and a 2-dethyl-6-nonyl-4-hydroxypiperidine. Journal of Natural Products, 51, 1188–1197. DOI: 10.1021/np50060a023. http://dx.doi.org/10.1021/np50060a02310.1021/np50060a023Search in Google Scholar PubMed

[13] Eliel, E. L., Manoharan, M., Hodgson, D. J., Eggleston, D. S., & Jeyaraman, R. (1982). Conformational analysis. 43. A boat-shaped piperidine ring in 3-thia-7-aza-6,8-diphenylbicyclo[3.3.1]nonan-9-ol. The Journal of Organic Chemistry, 47, 4353–4356. DOI: 10.1021/jo00143a041. http://dx.doi.org/10.1021/jo00143a04110.1021/jo00143a041Search in Google Scholar

[14] Ganellin, C. R., & Spickett, R. G. W. (1965). Compounds affecting the central nervous system. I. 4-Piperidones and related compounds. Journal of Medicinal Chemistry, 8, 619–625. DOI: 10.1021/jm00329a015. http://dx.doi.org/10.1021/jm00329a01510.1021/jm00329a015Search in Google Scholar PubMed

[15] Gu, H., Zheng, R., Zhang, X., & Xu, B. (2004). Facile onepot synthesis of bifunctional heterodimers of nanoparticles: A conjugate of quantum dot and magnetic nanoparticles. Journal of the American Chemical Society, 126, 5664–5665. DOI: 10.1021/ja0496423. http://dx.doi.org/10.1021/ja049642310.1021/ja0496423Search in Google Scholar PubMed

[16] Jeyaraman, R., Senthilkumar, U. P., & Bigler, P. (1995). Chemistry of N-nitroso compounds. 7. Conformational preferences of hexahydro-N1,N4-dinitroso-r-2,c-7-diphenyl-1H-1,4-diazepines: Use of modified 1D HOHAHA and NOE techniques. The Journal of Organic Chemistry, 60, 7461–7470. DOI: 10.1021/jo00128a018. http://dx.doi.org/10.1021/jo00128a01810.1021/jo00128a018Search in Google Scholar

[17] Juang, S.-S., Chang, M., Wang, L. F., Han, J. L., & Ong, C. W. (2005). One pot synthesis of fused [1,2-a]pyrrole from 1,6-dioxo-2,4-diene and haloalkyl primary amine. Tetrahedron, 61, 1693–1697. DOI: 10.1016/j.tet.2004.12.051. http://dx.doi.org/10.1016/j.tet.2004.12.05110.1016/j.tet.2004.12.051Search in Google Scholar

[18] Katritzky, A. R., & Fan, W. (1990). The chemistry of benzotriazole. A novel and versatile synthesis of 1-alkyl-, 1-aryl-, 1-(alkylamino)-, or 1-amido-substituted and of 1,2,6-trisubstituted piperidines from glutaraldehyde and primary amines or monosubstituted hydrazines. The Journal of Organic Chemistry, 55, 3205–3209. DOI: 10.1021/jo00297a041. http://dx.doi.org/10.1021/jo00297a04110.1021/jo00297a041Search in Google Scholar

[19] Ma, Y., Qian, C., Wang, L., & Yang, M. (2000). Lanthanide triflate catalyzed Biginelli reaction. One-pot synthesis of dihydropyrimidinones under solvent-free conditions. The Journal of Organic Chemistry, 65, 3864–3868. DOI: 10.1021/jo9919052. http://dx.doi.org/10.1021/jo991905210.1021/jo9919052Search in Google Scholar PubMed

[20] Menche, D., Arikan, F., Li, J., Rudolph, S., & Sasse, F. (2007). Efficient one-pot synthesis of biologically active polysubstituted aromatic amines. Bioorganic & Medicinal Chemistry, 15, 7311–7317. DOI: 10.1016/j.bmc.2007.08.048. http://dx.doi.org/10.1016/j.bmc.2007.08.04810.1016/j.bmc.2007.08.048Search in Google Scholar PubMed

[21] Mobio, I. G., Soldatenkov, A. T., Fedorov, V. O., Ageev, E. A., Sergeeva, N. D., Lin, S., Stashenko, E. E., Prostakov, N. S., Andreyeva, E. I., Minayev, L. I., Koltsova, S. S., Denisov, E. N., Kapitonenko, T. A., & Ovodenko, L. A. (1989). Synthesis and physiological activity of 2,3,6-triaryl-4-oxo (hydroxy, oximino, amino) piperidine. Khimiko Farmatsevticheskii Zhurnal, 23, 421–427. Search in Google Scholar

[22] Nikalje, M. D., Phukan, P., & Sudalai, A. (2000). Recent advances in clay-catalyzed organic transformations. Organic Preparations and Procedures International: The New Journal for Organic Synthesis, 32, 1–40. DOI: 10.1080/00304940009356743. http://dx.doi.org/10.1080/0030494000935674310.1080/00304940009356743Search in Google Scholar

[23] Nithya, P., Hathwar, V. R., Maiyalagan, T., Kazak, C., & Nawaz Khan, F. (2009). 1,3-Dimethyl-2,6-diphenylpiperidin-4-one. Acta Crystallographica Section E, E65, o439. DOI: 10.1107/S1600536809003419. http://dx.doi.org/10.1107/S160053680900341910.1107/S1600536809003419Search in Google Scholar PubMed PubMed Central

[24] Noller, C. R., & Baliah, V. (1948). The preparation of some piperidine derivatives by the Mannich reaction. Journal of the American Chemical Society, 70, 3853–3855. DOI: 10.1021/ja01191a092. http://dx.doi.org/10.1021/ja01191a09210.1021/ja01191a092Search in Google Scholar PubMed

[25] Pati, H. N., Das, U., Das, S., Bandy, B., De Clercq, E., Balzarini, J., Kawase, M., Sakagami, H., Quail, J. W., Stables, J. P., & Dimmock, J. R. (2009). The cytotoxic properties and preferential toxicity to tumour cells displayed by some 2,4-bis(benzylidene)-8-methyl-8-azabicyclo[3.2.1]octan-3-ones and 3,5-bis(benzylidene)-1-methyl-4-piperidones. European Journal of Medicinal Chemistry, 44, 54–62. DOI: 10.1016/j.ejmech.2008.03.015. http://dx.doi.org/10.1016/j.ejmech.2008.03.01510.1016/j.ejmech.2008.03.015Search in Google Scholar

[26] Polshettiwar, V., & Varma, R. S. (2008). Microwave-assisted organic synthesis and transformations using benign reaction media. Accounts of Chemical Research, 41, 629–639. DOI: 10.1021/ar700238s. http://dx.doi.org/10.1021/ar700238s10.1021/ar700238sSearch in Google Scholar

[27] Rameshkumar, N., Veena, A., Ilavarasan, R., Adiraj, M., Shanmugapandiyan, P., & Sridhar, S. K. (2003). Synthesis and biological activities of 2,6-diaryl-3-methyl-4-piperidone derivatives. Biological & Pharmaceutical Bulletin, 26, 188–193. DOI: 10.1248/bpb.26.188. http://dx.doi.org/10.1248/bpb.26.18810.1248/bpb.26.188Search in Google Scholar

[28] Roopan, S. M., & Nawaz Khan, F. R. (2010). ZnO nanorods catalyzed N-alkylation of piperidin-4-one, 4(3H)-pyrimidone, and ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenylquinoline-3-carboxylate. Chemical Papers, 64, 678–682. DOI: 10.2478/s11696-010-0045-3. http://dx.doi.org/10.2478/s11696-010-0045-310.2478/s11696-010-0045-3Search in Google Scholar

[29] Srinivasan, M., Perumal, S., & Selvaraj, S. (2006). Synthesis, stereochemistry, and antimicrobial activity of 2,6-diaryl-3-(arylthio)piperidin-4-ones. Chemical & Pharmaceutical Bulletin, 54, 795–801. DOI: 10.1248/cpb.54.795. http://dx.doi.org/10.1248/cpb.54.79510.1248/cpb.54.795Search in Google Scholar

[30] Srinivasan, M., Perumal, S., & Selvaraj, S. (2005). (L)-Proline catalysed efficient synthesis of 3-substituted 2,6-diarylpiperidin-4-ones. ARKIVOC, 2005(xi), 201–208. 10.3998/ark.5550190.0006.b17Search in Google Scholar

[31] Varma, R. S. (2002). Clay and clay-supported reagents in organic synthesis. Tetrahedron, 58, 1235–1255. DOI: 10.1016/S0040-4020(01)01216-9. http://dx.doi.org/10.1016/S0040-4020(01)01216-910.1016/S0040-4020(01)01216-9Search in Google Scholar

[32] Venkatesa Perumal, R., Adiraj, M., & Shanmuga Pandiyan, P. (2001). Synthesis, analgesic and anti inflammatory evaluation of substituted 4-piperidones. Indian Drugs, 38, 156–159. Search in Google Scholar

[33] Vijayalakshmi, R., Muthukumar, M., Ponnuswamy, S., & Jeyaraman, R. (2006). Competing A1,3 strain and Ph:Ph diaxial repulsion in oximes and semicarbazones of N-nitroso-r-2,c-6-diphenylpiperidin-4-ones. Indian Journal of Chemistry Section B, 45B, 2720–2735. Search in Google Scholar

[34] Weintraub, P. M., Sabol, J. S., Kane, J. M., & Borcherding, D. R. (2003). Recent advances in the synthesis of piperidones and piperidines. Tetrahedron, 59, 2953–2989. DOI: 10.1016/S0040-4020(03)00295-3. http://dx.doi.org/10.1016/S0040-4020(03)00295-310.1016/S0040-4020(03)00295-3Search in Google Scholar

[35] Zeng, H., Li, H., & Shao, H. (2009). One-pot three-component Mannich-type reactions using sulfamic acid catalyst under ultrasound irradiation. Ultrasonics Sonochemistry, 16, 758–762. DOI: 10.1016/j.ultsonch.2009.03.008. http://dx.doi.org/10.1016/j.ultsonch.2009.03.00810.1016/j.ultsonch.2009.03.008Search in Google Scholar PubMed