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Volumn 207, Issue , 2015, Pages 14-20

Oxalic acid dihydrate: Proline (LTTM) as a new generation solvent for synthesis of 3,3-diaryloxindole and chromone based bis(indolyl)alkanes: Green, chromatography free protocol

Author keywords

3 Formyl chromone; Group assistance purification (GAP); Indole; Isatin; Low transition temperature mixture (LTTM)

Indexed keywords

BIOACTIVITY; CARBONYL COMPOUNDS; CHROMATOGRAPHIC ANALYSIS; CONDENSATION REACTIONS; OXALIC ACID; POLYCYCLIC AROMATIC HYDROCARBONS; PURIFICATION; SYNTHESIS (CHEMICAL);

EID: 84925108802     PISSN: 01677322     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molliq.2015.02.036     Document Type: Article
Times cited : (21)

References (43)
  • 2
    • 0034098001 scopus 로고    scopus 로고
    • New bisindole alkaloids of the topsentin and hamacanthin classes from the Mediterranean Marine Sponge Rhaphisia lacazei
    • A. Casapullo, G. Bifulco, I. Bruno, and R. Riccio New bisindole alkaloids of the topsentin and hamacanthin classes from the Mediterranean Marine Sponge Rhaphisia lacazei J. Nat. Prod. 63 2000 447 451
    • (2000) J. Nat. Prod. , vol.63 , pp. 447-451
    • Casapullo, A.1    Bifulco, G.2    Bruno, I.3    Riccio, R.4
  • 3
    • 51549095960 scopus 로고    scopus 로고
    • Cancer chemotherapy with indole-3-carbinol, bis(3′-indolyl)methane and synthetic analogs
    • S. Safe, S. Papineni, and S. Chintharlapalli Cancer chemotherapy with indole-3-carbinol, bis(3′-indolyl)methane and synthetic analogs Cancer Lett. 269 2008 326 338
    • (2008) Cancer Lett. , vol.269 , pp. 326-338
    • Safe, S.1    Papineni, S.2    Chintharlapalli, S.3
  • 4
    • 0035881570 scopus 로고    scopus 로고
    • Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines
    • C. Bonnesen, I.M. Eggleston, and J.D. Hayes Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines Cancer Res. 61 2001 6120 6130
    • (2001) Cancer Res. , vol.61 , pp. 6120-6130
    • Bonnesen, C.1    Eggleston, I.M.2    Hayes, J.D.3
  • 5
    • 33645107038 scopus 로고    scopus 로고
    • 3,3′-Diindolylmethane is a novel topoisomerase IIα catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells
    • Y. Gong, G.L. Firestone, and L.F. Bjeldanes 3,3′-Diindolylmethane is a novel topoisomerase IIα catalytic inhibitor that induces S-phase retardation and mitotic delay in human hepatoma HepG2 cells Mol. Pharmacol. 69 2006 1320 1327
    • (2006) Mol. Pharmacol. , vol.69 , pp. 1320-1327
    • Gong, Y.1    Firestone, G.L.2    Bjeldanes, L.F.3
  • 6
    • 0028605225 scopus 로고
    • Vibrindole A, a metabolite of the marine bacterium, Vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish Ostracion cubicus
    • R. Bell, S. Carmeli, N. Sar, and N. Sar Vibrindole A, a metabolite of the marine bacterium, Vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish Ostracion cubicus J. Nat. Prod. 57 1994 1587 1590
    • (1994) J. Nat. Prod. , vol.57 , pp. 1587-1590
    • Bell, R.1    Carmeli, S.2    Sar, N.3    Sar, N.4
  • 7
    • 0028603513 scopus 로고
    • Marine natural products. XXXIV. Trisindoline, a new antibiotic indole trimer, produced by a bacterium of Vibrio sp. Separated from the marine sponge Hyrtios altum
    • M. Kobayashi, S. Aoki, K. Gato, K. Matsunami, M. Kurosu, and I. Kitagawa Marine natural products. XXXIV. Trisindoline, a new antibiotic indole trimer, produced by a bacterium of Vibrio sp. separated from the marine sponge Hyrtios altum Chem. Pharm. Bull. 42 1994 2449 2451
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 2449-2451
    • Kobayashi, M.1    Aoki, S.2    Gato, K.3    Matsunami, K.4    Kurosu, M.5    Kitagawa, I.6
  • 8
    • 33750893617 scopus 로고    scopus 로고
    • Synthesis and anti-microbial activity of pyrazolylbisindoles - Promising anti-fungal compounds
    • G. Sivaprasad, P.T. Perumal, V.R. Prabavathy, and N. Mathivanan Synthesis and anti-microbial activity of pyrazolylbisindoles - promising anti-fungal compounds Bioorg. Med. Chem. Lett. 16 2006 6302 6305
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 6302-6305
    • Sivaprasad, G.1    Perumal, P.T.2    Prabavathy, V.R.3    Mathivanan, N.4
  • 10
    • 78449295900 scopus 로고    scopus 로고
    • Synthesis, antimicrobial and antioxidant evaluation of quinolines and bis(indolyl)methanes
    • C. Praveen, D. Muralidharan, and P.T. Perumal Synthesis, antimicrobial and antioxidant evaluation of quinolines and bis(indolyl)methanes Bioorg. Med. Chem. Lett. 20 2010 7292 7296
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 7292-7296
    • Praveen, C.1    Muralidharan, D.2    Perumal, P.T.3
  • 11
    • 0019209247 scopus 로고
    • Studies of potential organo-fluorine antibacterial agents. Part 5: Synthesis and antibacterial activity of some new fluorine-containing indole-2,3-dione derivatives
    • K.C. Joshi, V.N. Pathak, and S.K. Jain Studies of potential organo-fluorine antibacterial agents. Part 5: synthesis and antibacterial activity of some new fluorine-containing indole-2,3-dione derivatives Pharmazie 35 1980 677 679
    • (1980) Pharmazie , vol.35 , pp. 677-679
    • Joshi, K.C.1    Pathak, V.N.2    Jain, S.K.3
  • 12
    • 0020686579 scopus 로고
    • Potential anticonvulsants VI: Condensation of isatins with cyclohexanone and other cyclic ketones
    • H. Pajouhesh, R. Parsons, and F.D. Popp Potential anticonvulsants VI: condensation of isatins with cyclohexanone and other cyclic ketones J. Pharm. Sci. 72 1983 318 321
    • (1983) J. Pharm. Sci. , vol.72 , pp. 318-321
    • Pajouhesh, H.1    Parsons, R.2    Popp, F.D.3
  • 13
    • 0021744762 scopus 로고
    • Potential anticonvulsants. IX. Some isatin hydrazones and related compounds
    • F.D. Pope Potential anticonvulsants. IX. Some isatin hydrazones and related compounds J. Heterocycl. Chem. 21 1984 1641 1645
    • (1984) J. Heterocycl. Chem. , vol.21 , pp. 1641-1645
    • Pope, F.D.1
  • 14
    • 0037366605 scopus 로고    scopus 로고
    • The combinatorial synthesis of bicyclic privileged structures or privileged substructures
    • D.A. Horton, G.T. Bourne, and M.L. Smythe The combinatorial synthesis of bicyclic privileged structures or privileged substructures Chem. Rev. 103 2003 893 930
    • (2003) Chem. Rev. , vol.103 , pp. 893-930
    • Horton, D.A.1    Bourne, G.T.2    Smythe, M.L.3
  • 15
    • 33748572906 scopus 로고    scopus 로고
    • Silica sulfuric acid a novel and heterogeneous catalyst for the synthesis of some new oxindole derivatives
    • J. Azizian, A.A. Mohammadi, N. Karimi, M.R. Mohammadizadeh, and A.R. Karimi Silica sulfuric acid a novel and heterogeneous catalyst for the synthesis of some new oxindole derivatives Catal. Commun. 7 2006 752 755
    • (2006) Catal. Commun. , vol.7 , pp. 752-755
    • Azizian, J.1    Mohammadi, A.A.2    Karimi, N.3    Mohammadizadeh, M.R.4    Karimi, A.R.5
  • 16
    • 77349115131 scopus 로고    scopus 로고
    • Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids
    • K. Rad-Moghadam, M. Sharifi-Kiasaraie, and H. Taheri-Amlashi Synthesis of symmetrical and unsymmetrical 3,3-di(indolyl)indolin-2-ones under controlled catalysis of ionic liquids Tetrahedron 66 2010 2316 2321
    • (2010) Tetrahedron , vol.66 , pp. 2316-2321
    • Rad-Moghadam, K.1    Sharifi-Kiasaraie, M.2    Taheri-Amlashi, H.3
  • 18
    • 30744466643 scopus 로고    scopus 로고
    • Facile synthesis of 3,3-di(heteroaryl)indolin-2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation
    • S.J. Ji, and S.Y. Wang Facile synthesis of 3,3-di(heteroaryl)indolin-2-one derivatives catalyzed by ceric ammonium nitrate (CAN) under ultrasound irradiation Tetrahedron 62 2006 1527 1535
    • (2006) Tetrahedron , vol.62 , pp. 1527-1535
    • Ji, S.J.1    Wang, S.Y.2
  • 19
    • 50649095921 scopus 로고    scopus 로고
    • Efficient synthesis of bis- and tris-indolylalkanes catalyzed by a Brønsted acid-surfactant catalyst in water
    • H. Parasa, D.S. Saikat, and K. Dilip Efficient synthesis of bis- and tris-indolylalkanes catalyzed by a Brønsted acid-surfactant catalyst in water Synth. Commun. 38 2008 2870 2880
    • (2008) Synth. Commun. , vol.38 , pp. 2870-2880
    • Parasa, H.1    Saikat, D.S.2    Dilip, K.3
  • 20
    • 84956908078 scopus 로고    scopus 로고
    • 2: An efficient and reusable catalyst for the synthesis of oxindole derivatives
    • 2: an efficient and reusable catalyst for the synthesis of oxindole derivatives J. Saudi Chem. Soc. 2014 10.1016/j.jscs.2014.09.002
    • (2014) J. Saudi Chem. Soc.
    • Haghighi, M.1    Nikoofar, K.2
  • 24
    • 84858705973 scopus 로고    scopus 로고
    • Iodine-catalyzed condensation of isatin with indoles: A facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity
    • B.V.S. Reddy, N. Rajeswari, M. Sarangapani, Y. Prashanthi, R.J. Ganji, and A. Addlagatta Iodine-catalyzed condensation of isatin with indoles: a facile synthesis of di(indolyl)indolin-2-ones and evaluation of their cytotoxicity Bioorg. Med. Chem. Lett. 22 2012 2460 2463
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 2460-2463
    • Reddy, B.V.S.1    Rajeswari, N.2    Sarangapani, M.3    Prashanthi, Y.4    Ganji, R.J.5    Addlagatta, A.6
  • 26
    • 84902978283 scopus 로고    scopus 로고
    • Rapid and efficient synthesis of 3,3-Di(1H-indol-3-yl)indolin-2-ones and 2,2-Di(1H-indol-3-yl)-2H-acenaphthen-1-ones catalyzed by p-TSA
    • J. Yu, T. Shen, Y. Lin, Y. Zhou, and Q. Song Rapid and efficient synthesis of 3,3-Di(1H-indol-3-yl)indolin-2-ones and 2,2-Di(1H-indol-3-yl)-2H-acenaphthen-1-ones catalyzed by p-TSA Synth. Commun. 44 2014 2029 2036
    • (2014) Synth. Commun. , vol.44 , pp. 2029-2036
    • Yu, J.1    Shen, T.2    Lin, Y.3    Zhou, Y.4    Song, Q.5
  • 27
    • 84880262548 scopus 로고    scopus 로고
    • Triphenylphosphine-m-sulfonate/carbon tetrabromide as an efficient and easily recoverable catalyst system for Friedel-Crafts alkylation of indoles with carbonyl compounds or acetals
    • C. Huo, C. Sun, C. Wang, X. Jia, and W. Chang Triphenylphosphine-m-sulfonate/carbon tetrabromide as an efficient and easily recoverable catalyst system for Friedel-Crafts alkylation of indoles with carbonyl compounds or acetals ACS Sustainable Chem. Eng. 1 2013 549 553
    • (2013) ACS Sustainable Chem. Eng. , vol.1 , pp. 549-553
    • Huo, C.1    Sun, C.2    Wang, C.3    Jia, X.4    Chang, W.5
  • 28
    • 45449087045 scopus 로고    scopus 로고
    • Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: Synthesis and some reactions of (chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones
    • V.Y. Sosnovskikh, R.A. Irgashev, and A.A. Levchenko Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: synthesis and some reactions of (chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones Tetrahedron 64 2008 6607 6614
    • (2008) Tetrahedron , vol.64 , pp. 6607-6614
    • Sosnovskikh, V.Y.1    Irgashev, R.A.2    Levchenko, A.A.3
  • 29
    • 34548691864 scopus 로고    scopus 로고
    • Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: Synthesis of (chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones under solvent-free conditions
    • V.Y. Sosnovskikh, and R.A. Irgashev Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: synthesis of (chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones under solvent-free conditions Tetrahedron Lett. 48 2007 7436 7439
    • (2007) Tetrahedron Lett. , vol.48 , pp. 7436-7439
    • Sosnovskikh, V.Y.1    Irgashev, R.A.2
  • 30
    • 34447101448 scopus 로고    scopus 로고
    • Design of sustainable chemical products, the example of ionic liquids
    • J. Ranke, S. Stolte, R. Stormann, J. Arning, and B. Jastorff Design of sustainable chemical products, the example of ionic liquids Chem. Rev. 107 2007 2183 2206
    • (2007) Chem. Rev. , vol.107 , pp. 2183-2206
    • Ranke, J.1    Stolte, S.2    Stormann, R.3    Arning, J.4    Jastorff, B.5
  • 31
    • 38349047179 scopus 로고    scopus 로고
    • Applications of ionic liquids in the chemical industry
    • N.V. Plechkova, and K.R. Seddon Applications of ionic liquids in the chemical industry Chem. Soc. Rev. 37 2008 123 150
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 123-150
    • Plechkova, N.V.1    Seddon, K.R.2
  • 32
    • 38749084957 scopus 로고    scopus 로고
    • Protic ionic liquids: Properties and applications
    • T.L. Greaves, and C.J. Drummond Protic Ionic Liquids: Properties and Applications Chem. Rev. 108 2008 206 237
    • (2008) Chem. Rev. , vol.108 , pp. 206-237
    • Greaves, T.L.1    Drummond, C.J.2
  • 33
    • 84874901900 scopus 로고    scopus 로고
    • Low-transitionerature mixtures (LTTMs): A new generation of designer solvents
    • M. Francisco, A. van den Bruinhorst, and M.C. Kroon Low-transitionerature mixtures (LTTMs): a new generation of designer solvents Angew. Chem. Int. Ed. 52 2013 3074 3085
    • (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 3074-3085
    • Francisco, M.1    Van Den Bruinhorst, A.2    Kroon, M.C.3
  • 34
    • 84879492207 scopus 로고    scopus 로고
    • Efficient deep eutectic solvents catalyzed synthesis of pyran and benzopyran derivatives
    • N. Azizi, S. Dezfooli, M. Khajeh, and M.M. Hashemi Efficient deep eutectic solvents catalyzed synthesis of pyran and benzopyran derivatives J. Mol. Liq. 186 2013 76 80
    • (2013) J. Mol. Liq. , vol.186 , pp. 76-80
    • Azizi, N.1    Dezfooli, S.2    Khajeh, M.3    Hashemi, M.M.4
  • 35
    • 84868691266 scopus 로고    scopus 로고
    • Highly efficient deep eutectic solvent catalyzed ring opening of epoxides
    • N. Azizi, and E. Batebi Highly efficient deep eutectic solvent catalyzed ring opening of epoxides Catal. Sci. Technol. 2 2012 2445 2448
    • (2012) Catal. Sci. Technol. , vol.2 , pp. 2445-2448
    • Azizi, N.1    Batebi, E.2
  • 36
    • 77949408165 scopus 로고    scopus 로고
    • Halogenation reactions in biodegradable solvent: Efficient bromination of substituted 1-aminoanthra-9, 10-quinone in deep eutectic solvent (choline chloride/:/urea)
    • S.B. Phadtare, and G.S. Shankarling Halogenation reactions in biodegradable solvent: efficient bromination of substituted 1-aminoanthra-9, 10-quinone in deep eutectic solvent (choline chloride/:/urea) Green Chem. 12 2010 458 462
    • (2010) Green Chem. , vol.12 , pp. 458-462
    • Phadtare, S.B.1    Shankarling, G.S.2
  • 37
    • 84893437841 scopus 로고    scopus 로고
    • Greener synthesis of spirooxindole in deep eutectic solvent
    • N. Azizi, S. Dezfooli, and M.M. Hashemi Greener synthesis of spirooxindole in deep eutectic solvent J. Mol. Liq. 194 2014 62 67
    • (2014) J. Mol. Liq. , vol.194 , pp. 62-67
    • Azizi, N.1    Dezfooli, S.2    Hashemi, M.M.3
  • 38
    • 84870055322 scopus 로고    scopus 로고
    • Lipase and deep eutectic mixture catalyzed efficient synthesis of thiazoles in water at room temperature
    • H.R. Lobo, B.S. Singh, and G.S. Shankarling Lipase and deep eutectic mixture catalyzed efficient synthesis of thiazoles in water at room temperature Catal. Lett. 142 2012 1369 1375
    • (2012) Catal. Lett. , vol.142 , pp. 1369-1375
    • Lobo, H.R.1    Singh, B.S.2    Shankarling, G.S.3
  • 39
    • 84872101094 scopus 로고    scopus 로고
    • Proficient synthesis of quinoxaline and phthalazinetrione derivatives using [C8dabco]Br ionic liquid as catalyst in aqueous media
    • A. Mulik, D. Chandam, P. Patil, D. Patil, S. Jagdale, and M. Deshmukh Proficient synthesis of quinoxaline and phthalazinetrione derivatives using [C8dabco]Br ionic liquid as catalyst in aqueous media J. Mol. Liq. 179 2013 104 109
    • (2013) J. Mol. Liq. , vol.179 , pp. 104-109
    • Mulik, A.1    Chandam, D.2    Patil, P.3    Patil, D.4    Jagdale, S.5    Deshmukh, M.6
  • 40
    • 84901845365 scopus 로고    scopus 로고
    • Novel Brønsted acidic ionic liquid ([CMIM][CF3COO]) prompted multicomponent hantzsch reaction for the eco-friendly synthesis of acridinediones: An efficient and recyclable catalyst
    • D.R. Patil, D.R. Chandam, A.G. Mulik, P.P. Patil, S.D. Jagdale, R. Kant, V. Gupta, and M.B. Deshmukh Novel Brønsted acidic ionic liquid ([CMIM][CF3COO]) prompted multicomponent hantzsch reaction for the eco-friendly synthesis of acridinediones: an efficient and recyclable catalyst Catal. Lett. 144 2014 949 958
    • (2014) Catal. Lett. , vol.144 , pp. 949-958
    • Patil, D.R.1    Chandam, D.R.2    Mulik, A.G.3    Patil, P.P.4    Jagdale, S.D.5    Kant, R.6    Gupta, V.7    Deshmukh, M.B.8
  • 41
    • 84921068182 scopus 로고    scopus 로고
    • (±)-Camphor-10-sulfonic acid catalyzed atom efficient and green synthesis of triazolo[1,2-a]indazole-triones and spiro triazolo[1,2-a]indazole-tetraones
    • D.R. Chandam, A.G. Mulik, P.P. Patil, S.D. Jagdale, D.R. Patil, and M.B. Deshmukh (±)-Camphor-10-sulfonic acid catalyzed atom efficient and green synthesis of triazolo[1,2-a]indazole-triones and spiro triazolo[1,2-a]indazole-tetraones Res. Chem. Intermed. 41 2015 761 771
    • (2015) Res. Chem. Intermed. , vol.41 , pp. 761-771
    • Chandam, D.R.1    Mulik, A.G.2    Patil, P.P.3    Jagdale, S.D.4    Patil, D.R.5    Deshmukh, M.B.6


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