메뉴 건너뛰기




Volumn 68, Issue 4, 2014, Pages 575-578

Natural organic acids promoted Beckmann rearrangement: Green and expeditious synthesis of amides under solvent-free conditions

Author keywords

amides; Beckmann rearrangement; natural organic acids; oximes; solvent free

Indexed keywords


EID: 84891492451     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-013-0481-y     Document Type: Article
Times cited : (22)

References (23)
  • 1
    • 0034303529 scopus 로고    scopus 로고
    • Recent advances in the synthesis of heterocycles from oximes
    • 1:CAS:528:DC%2BD3cXnt1WhsLk%3D 10.3987/REV-00-536
    • Abele, E., & Lukevics, E. (2000). Recent advances in the synthesis of heterocycles from oximes. Heterocycles, 53, 2285-2336. DOI: 10.3987/rev-00-536.
    • (2000) Heterocycles , vol.53 , pp. 2285-2336
    • Abele, E.1    Lukevics, E.2
  • 3
    • 84869491346 scopus 로고    scopus 로고
    • 5/silica catalysts: A comparative study
    • 1:CAS:528:DC%2BC38XhtVCjsb3J 10.1016/j.cattod.2012.01.043
    • 5/silica catalysts: A comparative study. Catalysis Today, 198, 289-299. DOI: 10.1016/j.cattod.2012.01.043.
    • (2012) Catalysis Today , vol.198 , pp. 289-299
    • Anilkumar, M.1    Hoelderich, W.F.2
  • 4
    • 0041834589 scopus 로고    scopus 로고
    • Ketones to amides via a formal Beckmann rearrangement in 'one pot': A solvent-free reaction promoted by anhydrous oxalic acid. Possible analogy with the Schmidt reaction
    • DOI 10.1016/j.tetlet.2003.08.038
    • Chandrasekhar, S., & Gopalaiah, K. (2003). Ketones to amides via a formal Beckmann rearrangement in 'one pot': a solventfree reaction promoted by anhydrous oxalic acid. Possible analogy with the Schmidt reaction. Tetrahedron Letters, 44, 7437-7439. DOI: 10.1016/j.tetlet.2003.08.038. (Pubitemid 37102973)
    • (2003) Tetrahedron Letters , vol.44 , Issue.40 , pp. 7437-7439
    • Chandrasekhar, S.1    Gopalaiah, K.2
  • 5
    • 0037008481 scopus 로고    scopus 로고
    • Practical approaches to green solvents
    • DOI 10.1126/science.1069622
    • DeSimone, J. M. (2002). Practical approaches to green solvents. Science, 297, 799-803. DOI: 10.1126/science.1069622. (Pubitemid 34839622)
    • (2002) Science , vol.297 , Issue.5582 , pp. 799-803
    • DeSimone, J.M.1
  • 8
    • 79953655021 scopus 로고    scopus 로고
    • Surfactant-directed zeolite nanosheets: A high-performance catalyst for gas-phase Beckmann rearrangement
    • 1:CAS:528:DC%2BC3MXislahu7c%3D 10.1021/cs100160g
    • Kim, J., Park, W., & Ryoo, R. (2011). Surfactant-directed zeolite nanosheets: A high-performance catalyst for gas-phase Beckmann rearrangement. ACS Catalysis, 1, 337-341. DOI: 10.1021/cs100160g.
    • (2011) ACS Catalysis , vol.1 , pp. 337-341
    • Kim, J.1    Park, W.2    Ryoo, R.3
  • 9
    • 11144343677 scopus 로고    scopus 로고
    • Highly efficient Beckmann rearrangement and dehydration of oximes
    • DOI 10.1016/j.tetlet.2004.11.116, PII S0040403904026188
    • Li, D., Shi, F., Guo, S., & Deng, Y. (2005). Highly efficient Beckmann rearrangement and dehydration of oximes. Tetrahedron Letters, 46, 671-674. DOI: 10.1016/j.tetlet.2004.11.116. (Pubitemid 40037927)
    • (2005) Tetrahedron Letters , vol.46 , Issue.4 , pp. 671-674
    • Li, D.1    Shi, F.2    Guo, S.3    Deng, Y.4
  • 11
    • 84865521756 scopus 로고    scopus 로고
    • Titanium cation-exchanged montmorillonite as an active heterogeneous catalyst for the Beckmann rearrangement under mild reaction conditions
    • 1:CAS:528:DC%2BC38XhtF2hsLzK 10.1016/j.tetlet.2012.07.032
    • Mitsudome, T., Matsuno, T., Sueoka, S., Mizugaki, T., Jitsukawa, K., & Kaneda, K. (2012). Titanium cation-exchanged montmorillonite as an active heterogeneous catalyst for the Beckmann rearrangement under mild reaction conditions. Tetrahedron Letters, 53, 5211-5214. DOI: 10.1016/j.tetlet.2012.07. 032.
    • (2012) Tetrahedron Letters , vol.53 , pp. 5211-5214
    • Mitsudome, T.1    Matsuno, T.2    Sueoka, S.3    Mizugaki, T.4    Jitsukawa, K.5    Kaneda, K.6
  • 12
    • 0000326760 scopus 로고
    • Beckmann rearrangement catalyzed by the combined use of tetrabutylammonium perrhenate(VII) and trifluoromethanesulfonic acid
    • 10.1246/cl.1993.489
    • Narasaka, K., Kusama, H., Yamashita, Y., & Sato, H. (1993). Beckmann rearrangement catalyzed by the combined use of tetrabutylammonium perrhenate(VII) and trifluoromethanesulfonic acid. Chemistry Letters, 22, 489-492. DOI: 10.1246/cl.1993.489.
    • (1993) Chemistry Letters , vol.22 , pp. 489-492
    • Narasaka, K.1    Kusama, H.2    Yamashita, Y.3    Sato, H.4
  • 13
    • 0006077638 scopus 로고    scopus 로고
    • Synthesis of medium-sized ring lactams
    • 1:CAS:528:DC%2BD3MXnsVCnsrc%3D 10.1007/3-540-44726-1-4
    • Nubbemeyer, U. (2001). Synthesis of medium-sized ring lactams. Topics in Current Chemistry, 216, 125-196. DOI: 10.1007/3-540-44726-1 4.
    • (2001) Topics in Current Chemistry , vol.216 , pp. 125-196
    • Nubbemeyer, U.1
  • 14
    • 84873726755 scopus 로고    scopus 로고
    • The effect of substrate size in the Beckmann rearrangement: MOFs vs
    • 1:CAS:528:DC%2BC38XhsFGjtrbO 10.1016/j.cattod.2012.09.008
    • Opanasenko, M., Shamzhy, M., Lamač, M., & Čejka, J. (2013). The effect of substrate size in the Beckmann rearrangement: MOFs vs. zeolites. Catalysis Today, 204, 94-100. DOI: 10.1016/j.cattod.2012.09.008.
    • (2013) Zeolites. Catalysis Today , vol.204 , pp. 94-100
    • Opanasenko, M.1    Shamzhy, M.2    Lamač, M.3    Čejka, J.4
  • 15
    • 0035921948 scopus 로고    scopus 로고
    • A principled stance
    • DOI 10.1038/35095133
    • Poliakoff, M., & Anastas, P. (2001). A principled stance. Nature, 413, 257. DOI: 10.1038/35095133. (Pubitemid 32905831)
    • (2001) Nature , vol.413 , Issue.6853 , pp. 257
    • Poliakoff, M.1    Anastas, P.2
  • 16
    • 84879780447 scopus 로고    scopus 로고
    • Extra-large-pore zeolites with UTL topology: Control of the catalytic activity by variation in the nature of the active sites
    • 1:CAS:528:DC%2BC3sXnvFSgsL4%3D 10.1002/cctc.201200925
    • Shamzhy, M. V., Shvets, O. V., Opanasenko, M. V., Kurfiř tová, L., Kubička, D., & Čejka, J. (2013). Extra-large-pore zeolites with UTL topology: Control of the catalytic activity by variation in the nature of the active sites. ChemCatChem, 5, 1891-1898. DOI: 10.1002/cctc.201200925.
    • (2013) ChemCatChem , vol.5 , pp. 1891-1898
    • Shamzhy, M.V.1    Shvets, O.V.2    Opanasenko, M.V.3    Kurfiřtová, L.4    Kubička, D.5    Čejka, J.6
  • 17
    • 67649252850 scopus 로고    scopus 로고
    • Cs exchanged phosphotungstic acid as an efficient catalyst for liquid-phase Beckmann rearrangement of oximes
    • 1:CAS:528:DC%2BD1MXnsFCjuro%3D 10.1016/j.apcatb.2009.04.016
    • Shiju, N. R., Williams, H. M., & Brown, D. R. (2009). Cs exchanged phosphotungstic acid as an efficient catalyst for liquid-phase Beckmann rearrangement of oximes. Applied Catalysis B: Environmental, 90, 451-457. DOI: 10.1016/j.apcatb.2009.04.016.
    • (2009) Applied Catalysis B: Environmental , vol.90 , pp. 451-457
    • Shiju, N.R.1    Williams, H.M.2    Brown, D.R.3
  • 18
    • 77951744157 scopus 로고    scopus 로고
    • Multicomponent eco-friendly synthesis of 3,4-dihydropyrimidine-2-(1H)- ones using an organocatalyst lactic acid
    • 10.1080/17518250902973833
    • Suresh, Saini, A., Kumar, D., & Sandhu, J. S. (2009). Multicomponent eco-friendly synthesis of 3,4-dihydropyrimidine-2-(1H)-ones using an organocatalyst lactic acid. Green Chemistry Letters and Reviews, 2, 29-33. DOI: 10.1080/17518250902973833.
    • (2009) Green Chemistry Letters and Reviews , vol.2 , pp. 29-33
    • Suresh1    Saini, A.2    Kumar, D.3    Sandhu, J.S.4
  • 19
    • 79956354556 scopus 로고    scopus 로고
    • Citric acid catalysed Beckmann rearrangement, under solvent free conditions
    • 1:CAS:528:DC%2BC3MXislaiu7k%3D 10.3184/174751911X557296
    • Thopate, S. R., Kote, S. R., Rohokale, S. V., & Thorat, N. M. (2011). Citric acid catalysed Beckmann rearrangement, under solvent free conditions. Journal of Chemical Research, 35, 124-125. DOI: 10.3184/174751911x557296.
    • (2011) Journal of Chemical Research , vol.35 , pp. 124-125
    • Thopate, S.R.1    Kote, S.R.2    Rohokale, S.V.3    Thorat, N.M.4
  • 20
    • 1842788776 scopus 로고    scopus 로고
    • Sulfamic acid as a cost-effective and recyclable catalyst for liquid Beckmann rearrangement, a green process to produce amides from ketoximes without waste
    • DOI 10.1016/j.tetlet.2004.03.017, PII S0040403904005234
    • Wang, B., Gu, Y., Luo, C., Yang, T., Yang, L., & Suo, J. (2004). Sulfamic acid as a cost-effective and recyclable catalyst for liquid Beckmann rearrangement, a green process to produce amides from ketoximes without waste. Tetrahedron Letters, 45, 3369-3372. DOI: 10.1016/j.tetlet.2004.03.017. (Pubitemid 38471613)
    • (2004) Tetrahedron Letters , vol.45 , Issue.17 , pp. 3369-3372
    • Wang, B.1    Gu, Y.2    Luo, C.3    Yang, T.4    Yang, L.5    Suo, J.6
  • 21
    • 34548396734 scopus 로고    scopus 로고
    • P-Toluenesulfonic acid mediated zinc chloride: Highly effective catalyst for the Beckmann rearrangement
    • DOI 10.1016/j.tetlet.2007.07.171, PII S0040403907015018
    • Xiao, L. F, Xia, C. G., & Chen, J. (2007). p-Toluenesulfonic acid mediated zinc chloride: highly effective catalyst for the Beckmann rearrangement. Tetrahedron Letters, 48, 7218-7221. DOI: 10.1016/j.tetlet.2007. 07.171. (Pubitemid 47361262)
    • (2007) Tetrahedron Letters , vol.48 , Issue.40 , pp. 7218-7221
    • Xiao, L.-f.1    Xia, C.-g.2    Chen, J.3
  • 22
    • 39249084585 scopus 로고    scopus 로고
    • Beckmann rearrangement of cyclohexanone oxime to É"- caprolactam catalyzed by sulfonic acid resin in DMSO
    • 1:CAS:528:DC%2BD1cXisVeqs7c%3D 10.1016/j.catcom.2008.01.011
    • You, K., Mao, L., Yin, D., Liu, P., & Luo, H. (2008). Beckmann rearrangement of cyclohexanone oxime to É"-caprolactam catalyzed by sulfonic acid resin in DMSO. Catalysis Communications, 9, 1521-1526. DOI: 10.1016/j.catcom.2008.01.011.
    • (2008) Catalysis Communications , vol.9 , pp. 1521-1526
    • You, K.1    Mao, L.2    Yin, D.3    Liu, P.4    Luo, H.5
  • 23
    • 40049100329 scopus 로고    scopus 로고
    • Sulfonic acid functionalised SBA-15 as catalysts for Beckmann rearrangement and esterification reaction
    • DOI 10.1007/s10934-007-9115-5, Advances in Porous Materials for Petrochemical Processing - China Perspective
    • Zhao, W., Salame, P., Launay, F., Gédéon, A., & Hao, Z. (2008). Sulfonic acid functionalised SBA-15 as catalysts for Beckmann rearrangement and esterification reaction. Journal of Porous Materials, 15, 139-143. DOI: 10.1007/s10934-007-9115-5. (Pubitemid 351322839)
    • (2008) Journal of Porous Materials , vol.15 , Issue.2 , pp. 139-143
    • Zhao, W.1    Salame, P.2    Launay, F.3    Gedeon, A.4    Hao, Z.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.