메뉴 건너뛰기




Volumn 13, Issue 12, 2008, Pages 3246-3252

Dodecatungstophosphoric acid (H3PW12O40), samarium and ruthenium (III) chloride catalyzed synthesis of unsaturated 2-phenyl-5(4H)-oxazolone derivatives under solvent-free conditions

Author keywords

2 Phenyl 5(4H) oxazolone; Dodecatungstophosphoric acid; Microwave irradiation; Ruthenium(III) chloride; Samarium

Indexed keywords

2 PHENYL 5(4H) OXAZOLONE; 2-PHENYL-5(4H)-OXAZOLONE; DODECATUNGSTOPHOSPHORIC ACID; DRUG DERIVATIVE; OXAZOLONE; PHOSPHORIC ACID; RUTHENIUM CHLORIDE; RUTHENIUM DERIVATIVE; SAMARIUM; SOLVENT; TUNGSTEN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 58149234164     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13123246     Document Type: Article
Times cited : (32)

References (31)
  • 1
    • 0013772243 scopus 로고
    • Some 2-fluoroethylamines derived from hydrocinnamic acid, phenylpyruvic acid and DL-phenylalanine
    • Martinez, A.P.; Lee, W.W.; Goodman, L. Some 2-fluoroethylamines derived from hydrocinnamic acid, phenylpyruvic acid and DL-phenylalanine. Tetrahedron 1964, 20, 2763-2771.
    • (1964) Tetrahedron , vol.20 , pp. 2763-2771
    • Martinez, A.P.1    Lee, W.W.2    Goodman, L.3
  • 2
    • 0031550595 scopus 로고    scopus 로고
    • 5(4H)-Oxazolone, part X. acid and base effects on the translactonization reaction of 4-(2-oxa-alkylidene)-5(4H)- oxazolones: New synthesis of 5-alkylidene-3-benzoylamino-2(5H)-furanones
    • Gelmi, M.L.; Clerici, F.; Melis, A. 5(4H)-Oxazolone, part X. acid and base effects on the translactonization reaction of 4-(2-oxa-alkylidene)-5(4H)- oxazolones: new synthesis of 5-alkylidene-3-benzoylamino-2(5H)-furanones. Tetrahedron 1997, 53, 1843-1854.
    • (1997) Tetrahedron , vol.53 , pp. 1843-1854
    • Gelmi, M.L.1    Clerici, F.2    Melis, A.3
  • 4
    • 0030221295 scopus 로고    scopus 로고
    • Diels-Alder reaction of (E)-2-phenyl-4-[(s)-2,2-dimethyl-1,3-dioxolan 4-ylmethylen]-5(4H)-oxazolone with heterogeneous catalysts
    • Cativiela, C.; Fraile, J.M.; Garcia, J. I.; Lopez, M. P.; Mayoral, J. A.; Pires, E. Diels-Alder reaction of (E)-2-phenyl-4-[(s)-2,2-dimethyl-1,3-dioxolan 4-ylmethylen]-5(4H)-oxazolone with heterogeneous catalysts. Tetrahedron Asymmetry 1996, 7, 2391-2394.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 2391-2394
    • Cativiela, C.1    Fraile, J.M.2    Garcia, J.I.3    Lopez, M.P.4    Mayoral, J.A.5    Pires, E.6
  • 5
    • 0007069097 scopus 로고
    • Ring transformation of Michael adducts of Benzylidene-5-oxazolones and 2-amino-1,3,4-thiadiazoles to antifungal 6,7-dihydro-5(H)-thiadiazolo[3,2- a] pyrimidin-5-ones
    • Singh, H.; Yadav, L.D.S.; Shukla, K.N.; Dwivedi, R. Ring transformation of Michael adducts of Benzylidene-5-oxazolones and 2-amino-1,3,4-thiadiazoles to antifungal 6,7-dihydro-5(H)-thiadiazolo[3,2- a] pyrimidin-5-ones. J. Agric. Food Chem. 1990, 38, 1962-1964.
    • (1990) J. Agric. Food Chem , vol.38 , pp. 1962-1964
    • Singh, H.1    Yadav, L.D.S.2    Shukla, K.N.3    Dwivedi, R.4
  • 7
    • 33746031797 scopus 로고    scopus 로고
    • Oxazolones: New tyrosinase inhibitors; synthesis and their structure-activity relationships
    • Khan, K.M.; Mughal, U.R.; Khan, M.T.H.; Ullah, Z.; Perveen, S.; Choudhary, M.I. Oxazolones: new tyrosinase inhibitors; synthesis and their structure-activity relationships. Bioorg. Med. Chem. 2006, 14, 6027-6033.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 6027-6033
    • Khan, K.M.1    Mughal, U.R.2    Khan, M.T.H.3    Ullah, Z.4    Perveen, S.5    Choudhary, M.I.6
  • 8
    • 0041330189 scopus 로고    scopus 로고
    • Synthesis and characterization of 4-ethoxymethylene-2-[1]-naphthyl- 5(4H)-oxazolone and its fluorescent amino acid derivatives
    • Koczan, G.; Csik, G.; Csampai, A.; Balog, E.; Bosze, S.; Sohar, P.; Hudecz, F. Synthesis and characterization of 4-ethoxymethylene-2-[1]-naphthyl- 5(4H)-oxazolone and its fluorescent amino acid derivatives. Tetrahedron 2001, 57, 4589-4598.
    • (2001) Tetrahedron , vol.57 , pp. 4589-4598
    • Koczan, G.1    Csik, G.2    Csampai, A.3    Balog, E.4    Bosze, S.5    Sohar, P.6    Hudecz, F.7
  • 9
    • 0034066185 scopus 로고    scopus 로고
    • Synthesis of conformationally constrained hydroxyl-α-amino acids by intramolecular conjucate addition
    • Avenoza, A.; Busto, J.H.; Cativiela, C.; Peregrina, J.M. Synthesis of conformationally constrained hydroxyl-α-amino acids by intramolecular conjucate addition. Aminoacids 2000, 18, 117-137.
    • (2000) Aminoacids , vol.18 , pp. 117-137
    • Avenoza, A.1    Busto, J.H.2    Cativiela, C.3    Peregrina, J.M.4
  • 10
    • 4644324049 scopus 로고    scopus 로고
    • Krasnov ,V.P.; Zhdanova, E.A.; Solieva, N.Z.; Sadretdinova, L.Sh.; Bukrina, I.M.; Demin, A.M.; Levit, G.L.; Ezhikova, M.A.; Kodess, M.I. Study of the effect of the nature of the side chain in esters of α-amino acids on the diastereoselectivity of condensation with 5(4H)-oxazolone in the synthesis of dipeptides with N-terminal N-acetylphenylalanine. Russ. Chem. Bull., Int. Ed. 2004, 53, 1331-1334.
    • Krasnov ,V.P.; Zhdanova, E.A.; Solieva, N.Z.; Sadretdinova, L.Sh.; Bukrina, I.M.; Demin, A.M.; Levit, G.L.; Ezhikova, M.A.; Kodess, M.I. Study of the effect of the nature of the side chain in esters of α-amino acids on the diastereoselectivity of condensation with 5(4H)-oxazolone in the synthesis of dipeptides with N-terminal N-acetylphenylalanine. Russ. Chem. Bull., Int. Ed. 2004, 53, 1331-1334.
  • 11
    • 0040844737 scopus 로고
    • Ring transformation of Michael adducts of Benzylidene-5-oxazolones and 3-mercapto-s-triazoles to 2,3-dihydro-4H-s-triazolo[3,4-b][1,3] thiazin-4-ones with some antifungal activity
    • Yadav, L.D.S.; Misra, A.R.; Singh, H. Ring transformation of Michael adducts of Benzylidene-5-oxazolones and 3-mercapto-s-triazoles to 2,3-dihydro-4H-s-triazolo[3,4-b][1,3] thiazin-4-ones with some antifungal activity. J. Agric. Food Chem. 1988, 36, 633-636.
    • (1988) J. Agric. Food Chem , vol.36 , pp. 633-636
    • Yadav, L.D.S.1    Misra, A.R.2    Singh, H.3
  • 12
    • 84987240577 scopus 로고
    • A fast synthesis of 2-acylamino-2-alkenoic acids
    • Tripathy, P.K.; Mukerjee, A.K. A fast synthesis of 2-acylamino-2-alkenoic acids. Synthesis 1984, 418- 422.
    • (1984) Synthesis , pp. 418-422
    • Tripathy, P.K.1    Mukerjee, A.K.2
  • 13
    • 37049048904 scopus 로고
    • The Erlenmeyer reaction with aliphatic aldehydes 2-phenyloxazol-5 one being used instead of hippuric acid
    • Crawford, M.; Little, W.T. The Erlenmeyer reaction with aliphatic aldehydes 2-phenyloxazol-5 one being used instead of hippuric acid. J. Chem. Soc. 1959, 729-731.
    • (1959) J. Chem. Soc , pp. 729-731
    • Crawford, M.1    Little, W.T.2
  • 14
    • 0000785501 scopus 로고
    • A new stereospecific synthesis of the E Isomers of 2-phenyl-4-arylmethylene-2-oxazoline-5-ones
    • Rao, Y.S. A new stereospecific synthesis of the E Isomers of 2-phenyl-4-arylmethylene-2-oxazoline-5-ones. J. Org. Chem. 1976, 722-724.
    • (1976) J. Org. Chem , pp. 722-724
    • Rao, Y.S.1
  • 15
    • 84987366742 scopus 로고
    • Condensation of 2-substituted 5-oxo-4,5dihydro-1,3-oxazoles with imines and their corresponding carbonyl compounds
    • Kumar, P. Mishra, H.D.; Mukerjee, A.K. Condensation of 2-substituted 5-oxo-4,5dihydro-1,3-oxazoles with imines and their corresponding carbonyl compounds. Synthesis 1980, 836-839.
    • (1980) Synthesis , pp. 836-839
    • Kumar, P.1    Mishra, H.D.2    Mukerjee, A.K.3
  • 16
    • 0033555849 scopus 로고    scopus 로고
    • Beccalli, E.M.; Clerici, F.; Gelmi, M.L. 5(4H)-Oxazolone. Part XIII. A new synthesis of 4-arylidene-5(4H)-oxazolones by the stille reaction. Tetrahedron 1999, 55, 781-786.
    • Beccalli, E.M.; Clerici, F.; Gelmi, M.L. 5(4H)-Oxazolone. Part XIII. A new synthesis of 4-arylidene-5(4H)-oxazolones by the stille reaction. Tetrahedron 1999, 55, 781-786.
  • 17
    • 33646085776 scopus 로고    scopus 로고
    • Novel Synthesis of unsaturated 5(4H)-oxazolone derivatives with using palladium(II) acetate as a catalyst and microwave irradiation in solvent-free condition
    • Hamidian, H.; Momeni, A. Novel Synthesis of unsaturated 5(4H)-oxazolone derivatives with using palladium(II) acetate as a catalyst and microwave irradiation in solvent-free condition. Hetrocycl. Commun. 2006, 12, 29-34.
    • (2006) Hetrocycl. Commun , vol.12 , pp. 29-34
    • Hamidian, H.1    Momeni, A.2
  • 18
    • 0347627365 scopus 로고    scopus 로고
    • Calcium acetate catalyzed synthesis of 4-arylidene-2-phenyl- 5(4H)-oxazolones under solvent-free conditions
    • Paul, S.; Nanda, P.; Gupta, R.; Loupy, A. Calcium acetate catalyzed synthesis of 4-arylidene-2-phenyl- 5(4H)-oxazolones under solvent-free conditions. Tetrahedron Lett. 2004, 45, 425-427.
    • (2004) Tetrahedron Lett , vol.45 , pp. 425-427
    • Paul, S.1    Nanda, P.2    Gupta, R.3    Loupy, A.4
  • 19
    • 33845902542 scopus 로고    scopus 로고
    • Erlenmeyer azlactone synthesis with aliphatic aldehydes under solvent-free microwave conditions
    • Chandrasekhar, S.; Karri, P. Erlenmeyer azlactone synthesis with aliphatic aldehydes under solvent-free microwave conditions. Tetrahedron Lett. 2007, 48, 785-786.
    • (2007) Tetrahedron Lett , vol.48 , pp. 785-786
    • Chandrasekhar, S.1    Karri, P.2
  • 21
    • 0035742306 scopus 로고    scopus 로고
    • Dry media reactions
    • Kidwai, M. Dry media reactions. Pure Appl. Chem. 2001, 73, 147-151.
    • (2001) Pure Appl. Chem , vol.73 , pp. 147-151
    • Kidwai, M.1
  • 22
    • 36549081284 scopus 로고    scopus 로고
    • 40) as a highly efficient catalyst for the amidation of alcohols and protected alcohols with nitriles in water: A modified Ritter reaction
    • 40) as a highly efficient catalyst for the amidation of alcohols and protected alcohols with nitriles in water: a modified Ritter reaction. Catal. Commun. 2008, 9, 529-531.
    • (2008) Catal. Commun , vol.9 , pp. 529-531
    • Firouzabadi, H.1    Iranpoor, N.2    Khoshnood, A.3
  • 25
    • 33747584626 scopus 로고    scopus 로고
    • An eco-friendly catalytic route for synthesis of 4-amino-pyrazolo[3,4-d] pyrimidine derivatives by Keggin heteropolyacids under classical heating and microwave irradiation
    • Heravi, M.; Rajabzadeh, G.; Bamoharram, F.; Seifi, N. An eco-friendly catalytic route for synthesis of 4-amino-pyrazolo[3,4-d] pyrimidine derivatives by Keggin heteropolyacids under classical heating and microwave irradiation. J. Mol. Catal. Chem. A. 2006, 256, 238-241.
    • (2006) J. Mol. Catal. Chem. A , vol.256 , pp. 238-241
    • Heravi, M.1    Rajabzadeh, G.2    Bamoharram, F.3    Seifi, N.4
  • 26
    • 0037019987 scopus 로고    scopus 로고
    • Dehydration of alcohols
    • Khenkin, A.M.; Neumann, R. Dehydration of alcohols. J. Org. Chem. 2002, 67, 7075-7079.
    • (2002) J. Org. Chem , vol.67 , pp. 7075-7079
    • Khenkin, A.M.1    Neumann, R.2
  • 27
    • 33646468149 scopus 로고    scopus 로고
    • 40. J. Mol. Catal. Chem. A. 2006, 249, 1-3.
    • 40. J. Mol. Catal. Chem. A. 2006, 249, 1-3.
  • 28
    • 0037450491 scopus 로고    scopus 로고
    • A new strategy for the synthesis of α, β-diaroylpropionates promoted by samarium metal in DMF
    • Liu, Y.J.; Liu X.; Zhang, Y.M. A new strategy for the synthesis of α, β-diaroylpropionates promoted by samarium metal in DMF. Tetrahedron Lett. 2003, 44, 1667-1670.
    • (2003) Tetrahedron Lett , vol.44 , pp. 1667-1670
    • Liu, Y.J.1    Liu, X.2    Zhang, Y.M.3
  • 29
    • 0742322002 scopus 로고    scopus 로고
    • Stereo- and regiospecific four-molecule reaction of aroyl chlorides with iso- pentylene: Direct formation of (E)-β, γ-unsaturated carbonyl compounds promoted by samarium metal in DMF
    • Liu Y.J.; Zhang, Y.M. Stereo- and regiospecific four-molecule reaction of aroyl chlorides with iso- pentylene: direct formation of (E)-β, γ-unsaturated carbonyl compounds promoted by samarium metal in DMF. Tetrahedron Lett. 2004, 45, 1295-1298.
    • (2004) Tetrahedron Lett , vol.45 , pp. 1295-1298
    • Liu, Y.J.1    Zhang, Y.M.2
  • 30
    • 4544220805 scopus 로고    scopus 로고
    • A convenient and highly efficient method for the protection of aldehydes using very low loading hydrous ruthenium trichloride as catalyst
    • Qi, J.Y.; Ji, J.X.; Yueng, C.H.; Kwong, H.L.; Chen, A.S.C. A convenient and highly efficient method for the protection of aldehydes using very low loading hydrous ruthenium trichloride as catalyst. Tetrahedron Lett. 2004, 45, 7719-7721.
    • (2004) Tetrahedron Lett , vol.45 , pp. 7719-7721
    • Qi, J.Y.1    Ji, J.X.2    Yueng, C.H.3    Kwong, H.L.4    Chen, A.S.C.5
  • 31
    • 0344413547 scopus 로고    scopus 로고
    • RuCl3- Promoted amide formation from azides and thioacids
    • Fabio, F.; Wong, C.H. RuCl3- Promoted amide formation from azides and thioacids. Tetrahedron Lett. 2003, 44, 9083-9085.
    • (2003) Tetrahedron Lett , vol.44 , pp. 9083-9085
    • Fabio, F.1    Wong, C.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.