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Volumn 39, Issue 13, 2009, Pages 2288-2296

Iodine-catalyzed mild and efficient method for the synthesis of chalcones

Author keywords

Chalcone synthesis; Claisen Schmidt reaction; Iodine catalyst

Indexed keywords

1 (4 CHLOROPHENYL) 3 (2 METHOXYPHENYL)PROPENONE; 1 (4 CHLOROPHENYL) 3 (3 ETHOXY 4 HYDROXYPHENYL)PROPENONE; 1 (4 CHLOROPHENYL) 3 (4 ETHOXYPHENYL)PROPENONE; 3 (2 METHOXYPHENYL) 1 (4 METHOXYPHENYL)PROPENONE; 3 (2 METHOXYPHENYL) 1 4 TOLYLPROPENONE; 3 (2 METHOXYPHENYL) 1 PHENYLPROPENONE; 3 (3 ETHOXY 4 HYDROXYPHENYL) 1 (4 METHOXYPHENYL)PROPENONE; 3 (3 ETHOXY 4 HYDROXYPHENYL) 1 4 TOLYLPROPENONE; 3 (4 ETHOXYPHENYL) 1 (4 METHOXYPHENYL)PROPENONE; 3 (4 ETHOXYPHENYL) 1 4 TOLYLPROPENONE; 3 (4 ETHOXYPHENYL) 1 PHENYLPROPENONE; ACETOPHENONE DERIVATIVE; CHALCONE DERIVATIVE; IODINE; UNCLASSIFIED DRUG;

EID: 67650330824     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802654724     Document Type: Article
Times cited : (26)

References (33)
  • 1
    • 0032547898 scopus 로고    scopus 로고
    • Antileishmanial chalcones: Statistical design, synthesis, and threedimensional quantitative structure-activity relationship analysis
    • Nielsen, S. F.; Christensen, S. B.; Cruciani, G.; Kharazmi, A.; Liljefors, T. Antileishmanial chalcones: Statistical design, synthesis, and threedimensional quantitative structure-activity relationship analysis. J. Med. Chem. 1998, 41, 4819-4832.
    • (1998) J. Med. Chem , vol.41 , pp. 4819-4832
    • Nielsen, S.F.1    Christensen, S.B.2    Cruciani, G.3    Kharazmi, A.4    Liljefors, T.5
  • 3
    • 0030828189 scopus 로고    scopus 로고
    • A facile synthesis of 6-C-prenylflavanones
    • Bu, X.; Zhao, L.; Li, Y. A facile synthesis of 6-C-prenylflavanones. Synthesis 1997, 1246-1248.
    • (1997) Synthesis , pp. 1246-1248
    • Bu, X.1    Zhao, L.2    Li, Y.3
  • 4
    • 0029917360 scopus 로고    scopus 로고
    • Synthesis of exiguaflavanone K and (±)- leachianone
    • Bu, X.; Li, Y. G. Synthesis of exiguaflavanone K and (±)- leachianone. J. Nat. Prod. 1996, 59, 968-969.
    • (1996) J. Nat. Prod , vol.59 , pp. 968-969
    • Bu, X.1    Li, Y.G.2
  • 5
    • 0000965112 scopus 로고
    • Synthesis of 2'-hydroxychalcones and related compounds in interfacial solid-liquid conditions
    • Alcantara, A. R.; Marinas, J. M.; Sinisterra, J. V. Synthesis of 2'-hydroxychalcones and related compounds in interfacial solid-liquid conditions. Tetrahedron Lett. 1987, 28, 1515-1518.
    • (1987) Tetrahedron Lett , vol.28 , pp. 1515-1518
    • Alcantara, A.R.1    Marinas, J.M.2    Sinisterra, J.V.3
  • 6
    • 2542633525 scopus 로고
    • Base catalysis for fine chemicals production: Claisen-Schmidt condensation on zeolites and hydrotalcites for the production of chalcones and flavanones of pharmaceutical interest
    • Climent, M. J.; Corma, A.; Iborra, S.; Primo, J. Base catalysis for fine chemicals production: Claisen-Schmidt condensation on zeolites and hydrotalcites for the production of chalcones and flavanones of pharmaceutical interest. J. Catal. 1995, 15, 60-66.
    • (1995) J. Catal , vol.15 , pp. 60-66
    • Climent, M.J.1    Corma, A.2    Iborra, S.3    Primo, J.4
  • 7
    • 0033600699 scopus 로고    scopus 로고
    • Organolithium-mediated synthesis of prenylchalcones as potential inhibitors of chemoresistance
    • Daskiewicz, J. B.; Comte, G.; Barron, D.; Pietro, A. D.; Thomasson, F. Organolithium-mediated synthesis of prenylchalcones as potential inhibitors of chemoresistance. Tetrahedron Lett. 1999, 40, 7095-7098.
    • (1999) Tetrahedron Lett , vol.40 , pp. 7095-7098
    • Daskiewicz, J.B.1    Comte, G.2    Barron, D.3    Pietro, A.D.4    Thomasson, F.5
  • 8
    • 0035813417 scopus 로고    scopus 로고
    • Calcined sodium nitrate=natural phosphate: An extremely active catalyst for the easy synthesis of chalcones in heterogeneous media
    • Sebti, S.; Solhy, A.; Tahir, R.; Boulaajaj, S.; Mayoral, J. A.; Fraile, J. M.; Kossir, A.; Oumimoun, H. Calcined sodium nitrate=natural phosphate: An extremely active catalyst for the easy synthesis of chalcones in heterogeneous media. Tetrahedron Lett. 2001, 42, 7953-7955.
    • (2001) Tetrahedron Lett , vol.42 , pp. 7953-7955
    • Sebti, S.1    Solhy, A.2    Tahir, R.3    Boulaajaj, S.4    Mayoral, J.A.5    Fraile, J.M.6    Kossir, A.7    Oumimoun, H.8
  • 9
    • 1642338666 scopus 로고    scopus 로고
    • Dramatic activity enhancement of natural phosphate catalyst by lithium nitrate: An efficient synthesis of chalcones
    • Sebti, S.; Solhy, A.; Smahi, A.; Kossir, A.; Oumimoun, H. Dramatic activity enhancement of natural phosphate catalyst by lithium nitrate: An efficient synthesis of chalcones. Catal. Commun. 2002, 3, 335-339.
    • (2002) Catal. Commun , vol.3 , pp. 335-339
    • Sebti, S.1    Solhy, A.2    Smahi, A.3    Kossir, A.4    Oumimoun, H.5
  • 10
    • 0006376042 scopus 로고
    • Reactions in the presence of metallic halides, I: B-Unsaturated ketone formation as a side reaction in Friedel-Crafts acylations
    • Calloway, N. O.; Green, L. D. Reactions in the presence of metallic halides, I: b-Unsaturated ketone formation as a side reaction in Friedel-Crafts acylations. J. Am. Chem. Soc. 1937, 59, 809-811.
    • (1937) J. Am. Chem. Soc , vol.59 , pp. 809-811
    • Calloway, N.O.1    Green, L.D.2
  • 11
    • 31044441867 scopus 로고
    • New nitro chalcones
    • Sz'ell, T.; Sohalr, I. New nitro chalcones. Can. J. Chem. 1969, 47, 1254-1258.
    • (1969) Can. J. Chem , vol.47 , pp. 1254-1258
    • Sz'ell, T.1    Sohalr, I.2
  • 12
    • 0019015570 scopus 로고
    • Aldal condensations with metal(II) complex catalysts
    • Irie, K.; Watanabe, K. Aldal condensations with metal(II) complex catalysts. Bull. Chem. Soc. Jpn. 1980, 53, 1366-1371.
    • (1980) Bull. Chem. Soc. Jpn , vol.53 , pp. 1366-1371
    • Irie, K.1    Watanabe, K.2
  • 13
    • 85027618103 scopus 로고
    • An improved synthesis of 1,3 dibenzyl-2-buten-1- ones (b-methyl chalcones)
    • Mazza, L.; Guaram, A. An improved synthesis of 1,3 dibenzyl-2-buten-1- ones (b-methyl chalcones). Synthesis 1980, 41-44.
    • (1980) Synthesis , pp. 41-44
    • Mazza, L.1    Guaram, A.2
  • 14
    • 0000524247 scopus 로고
    • Cross-condensation reactions of cycloalkanones with aldehydes and primary alcohols under the influence of zirconocene complexes
    • Nakano, T.; Irifune, S.; Umano, S.; Inada, A.; Ishii, Y.; Ogawa, M. Cross-condensation reactions of cycloalkanones with aldehydes and primary alcohols under the influence of zirconocene complexes. J. Org. Chem. 1987, 52, 2239-2244.
    • (1987) J. Org. Chem , vol.52 , pp. 2239-2244
    • Nakano, T.1    Irifune, S.2    Umano, S.3    Inada, A.4    Ishii, Y.5    Ogawa, M.6
  • 15
    • 0032490931 scopus 로고    scopus 로고
    • 3 catalyses aldol condensations of aldehydes and ketones
    • 3 catalyses aldol condensations of aldehydes and ketones. Tetrahedron 1998, 54, 9475-9480.
    • (1998) Tetrahedron , vol.54 , pp. 9475-9480
    • Iranpoor, N.1    Kazemi, F.2
  • 16
    • 34047174521 scopus 로고    scopus 로고
    • A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride-etherate
    • Narender, T.; Papi Reddy, K. A simple and highly efficient method for the synthesis of chalcones by using borontrifluoride-etherate. Tetrahedron Lett. 2007, 48, 3177-3180.
    • (2007) Tetrahedron Lett , vol.48 , pp. 3177-3180
    • Narender, T.1    Papi Reddy, K.2
  • 17
    • 0038582672 scopus 로고    scopus 로고
    • A new solvent-free synthesis of α,α'-dibenzylidene cycloalkanones from acetals with cycloalkanones under microwave irradiation
    • Huang, D. F.; Wang, J. X.; Hu, Y. L. A new solvent-free synthesis of α,α'-dibenzylidene cycloalkanones from acetals with cycloalkanones under microwave irradiation. Chin. Chem. Lett. 2003, 14, 333-334.
    • (2003) Chin. Chem. Lett , vol.14 , pp. 333-334
    • Huang, D.F.1    Wang, J.X.2    Hu, Y.L.3
  • 18
    • 36248939221 scopus 로고    scopus 로고
    • 2=EtOH: Catalytic system for synthesis of chalcones
    • 2=EtOH: Catalytic system for synthesis of chalcones. Catal. Commun. 2008, 9, 315-316.
    • (2008) Catal. Commun , vol.9 , pp. 315-316
    • Petrov, O.1    Ianova, Y.2    Gerova, M.3
  • 19
    • 38149139219 scopus 로고    scopus 로고
    • Brønsted acidic ionic liquids as dual catalyst and solvent for environmentally friendly synthesis of chalcone
    • Shen, J.; Wang, H.; Lia, H.; Sun, Y.; Liu, Z. Brønsted acidic ionic liquids as dual catalyst and solvent for environmentally friendly synthesis of chalcone. J. Mol. Catal. A: Chem. 2008, 280, 24-28.
    • (2008) J. Mol. Catal. A: Chem , vol.280 , pp. 24-28
    • Shen, J.1    Wang, H.2    Lia, H.3    Sun, Y.4    Liu, Z.5
  • 20
    • 33748699338 scopus 로고    scopus 로고
    • Synthetic use of molecular iodine for organic sI'ntesis
    • Togo, H.; Iida, S. Synthetic use of molecular iodine for organic sI'ntesis. Synlett 2006, 2159-2175.
    • (2006) Synlett , pp. 2159-2175
    • Togo, H.1    Iida, S.2
  • 21
    • 33646767134 scopus 로고    scopus 로고
    • Lin, X.-F.; Cui, S.-L.; Wang, Y.-G. A highly efficient synthesis of 1,2,3,4- tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers. Tetrahedron Lett. 2006, 47, 4509-4512.
    • Lin, X.-F.; Cui, S.-L.; Wang, Y.-G. A highly efficient synthesis of 1,2,3,4- tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers. Tetrahedron Lett. 2006, 47, 4509-4512.
  • 22
    • 19944401847 scopus 로고    scopus 로고
    • Molecular iodine-catalyzed one-pot synthesis of 1,5-benzodiazepine derivatives under solvent-free conditions
    • Chen, W.-Y.; Lu, J. Molecular iodine-catalyzed one-pot synthesis of 1,5-benzodiazepine derivatives under solvent-free conditions. Synlett 2005, 1337-1339.
    • (2005) Synlett , pp. 1337-1339
    • Chen, W.-Y.1    Lu, J.2
  • 23
    • 20344382252 scopus 로고    scopus 로고
    • Iodine as a novel and efficient reagent for the synthesis of a-aminonitriles by a three-component condensation of carbonyl compounds, amines, and trimethylsilyl cyanide
    • Royer, L.; De, S. K.; Gibbs, R. A. Iodine as a novel and efficient reagent for the synthesis of a-aminonitriles by a three-component condensation of carbonyl compounds, amines, and trimethylsilyl cyanide. Tetrahedron Lett. 2005, 46, 4595-4597.
    • (2005) Tetrahedron Lett , vol.46 , pp. 4595-4597
    • Royer, L.1    De, S.K.2    Gibbs, R.A.3
  • 24
    • 17744376784 scopus 로고    scopus 로고
    • Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition
    • Banik, B. K.; Fernandez, M.; Alvarez, C. Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition. Tetrahedron Lett. 2005, 46, 2479-2482.
    • (2005) Tetrahedron Lett , vol.46 , pp. 2479-2482
    • Banik, B.K.1    Fernandez, M.2    Alvarez, C.3
  • 25
    • 22544457892 scopus 로고    scopus 로고
    • Molecular iodine-catalyzed onepot synthesis of 4-substituted-1,4-dihydropyridine derivatives via Hantzsch reaction
    • Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C.-F. Molecular iodine-catalyzed onepot synthesis of 4-substituted-1,4-dihydropyridine derivatives via Hantzsch reaction. Tetrahedron Lett. 2005, 46, 5771-5774.
    • (2005) Tetrahedron Lett , vol.46 , pp. 5771-5774
    • Ko, S.1    Sastry, M.N.V.2    Lin, C.3    Yao, C.-F.4
  • 26
    • 9644287844 scopus 로고    scopus 로고
    • Molecular iodine
    • Wang, S.-Y. Molecular iodine. Synlett. 2004, 2642-2643.
    • (2004) Synlett , pp. 2642-2643
    • Wang, S.-Y.1
  • 27
    • 33847063493 scopus 로고    scopus 로고
    • Iodine as a versatile reagent for the Prins-cyclization: An expeditious synthesis of 4-iodotetrahydropyran derivatives
    • Yadav, J. S.; Reddy, B. V. S.; Narayana Kumar, G. G. K. S.; Swamy, T. Iodine as a versatile reagent for the Prins-cyclization: An expeditious synthesis of 4-iodotetrahydropyran derivatives. Tetrahedron Lett. 2007, 48, 2205-2208.
    • (2007) Tetrahedron Lett , vol.48 , pp. 2205-2208
    • Yadav, J.S.1    Reddy, B.V.S.2    Narayana Kumar, G.G.K.S.3    Swamy, T.4
  • 28
    • 15244360267 scopus 로고    scopus 로고
    • First example of the activation of polymethylhydrosiloxane with molecular iodine: A facile synthesis of 3,6-dihydropyran derivatives
    • Yadav, J. S.; Reddy, B. V. S.; Premalatha, K.; Swamy, T. First example of the activation of polymethylhydrosiloxane with molecular iodine: A facile synthesis of 3,6-dihydropyran derivatives. Tetrahedron Lett. 2005, 46, 2687-2690.
    • (2005) Tetrahedron Lett , vol.46 , pp. 2687-2690
    • Yadav, J.S.1    Reddy, B.V.S.2    Premalatha, K.3    Swamy, T.4
  • 29
    • 0034816362 scopus 로고    scopus 로고
    • Iodinecatalyzed stereo selective synthesis of allyl glycosides, glycosyl cyanides, and glycosyl azides
    • Yadav, J. S.; Reddy, B. V. S.; Rao, C. V.; Chand, P. K.; Prasad, A. R. Iodinecatalyzed stereo selective synthesis of allyl glycosides, glycosyl cyanides, and glycosyl azides. Synlett 2001, 1638-1640.
    • (2001) Synlett , pp. 1638-1640
    • Yadav, J.S.1    Reddy, B.V.S.2    Rao, C.V.3    Chand, P.K.4    Prasad, A.R.5
  • 30
    • 0033248532 scopus 로고    scopus 로고
    • Iodine-catalyzed mild and efficient tetrahydropyranylation=depyranylation of alcohols
    • Kumar, H. M. S.; Reddy, B. V. S.; Reddy, E. J.; Yadav, J. S. Iodine-catalyzed mild and efficient tetrahydropyranylation=depyranylation of alcohols. Chem. Lett. 1999, 9, 857-858.
    • (1999) Chem. Lett , vol.9 , pp. 857-858
    • Kumar, H.M.S.1    Reddy, B.V.S.2    Reddy, E.J.3    Yadav, J.S.4
  • 31
    • 35748964126 scopus 로고    scopus 로고
    • Iodine-catalyzed coupling of 4-hydroxyl proline with isatins: An expeditious synthesis of 3-pyrrolyl indolin-2-ones
    • Yadav, J. S.; Reddy, B. V. S.; Ruchi, J.; Reddy, U. V. S. Iodine-catalyzed coupling of 4-hydroxyl proline with isatins: An expeditious synthesis of 3-pyrrolyl indolin-2-ones. J. Mol. Catal. A: Chem. 2007, 278, 38-41.
    • (2007) J. Mol. Catal. A: Chem , vol.278 , pp. 38-41
    • Yadav, J.S.1    Reddy, B.V.S.2    Ruchi, J.3    Reddy, U.V.S.4
  • 32
    • 34548202217 scopus 로고    scopus 로고
    • Synthesis of α,α'- bis(arylmethylidene) cycloalkanones catalyzed by molecular iodine: An improved procedure for the Claisen-Schmidt condensation
    • Pasha, M. A.; Jayashankara, V. P. Synthesis of α,α'- bis(arylmethylidene) cycloalkanones catalyzed by molecular iodine: An improved procedure for the Claisen-Schmidt condensation. Indian J. Chem. 2007, 46B, 1025-1027.
    • (2007) Indian J. Chem , vol.46 B , pp. 1025-1027
    • Pasha, M.A.1    Jayashankara, V.P.2
  • 33
    • 33644601223 scopus 로고    scopus 로고
    • Convenient and facile cross-aldol condensation catalyzed by molecular iodine: An efficient synthesis of a,a'-bis(substituted-benzylidene) cycloalkanones
    • Das, B.; Thirupathi, P.; Mahender, I.; Ravinder Reddy, K. Convenient and facile cross-aldol condensation catalyzed by molecular iodine: An efficient synthesis of a,a'-bis(substituted-benzylidene) cycloalkanones. J. Mol. Catal. A: Chem. 2006, 247, 182-185.
    • (2006) J. Mol. Catal. A: Chem , vol.247 , pp. 182-185
    • Das, B.1    Thirupathi, P.2    Mahender, I.3    Ravinder Reddy, K.4


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