메뉴 건너뛰기




Volumn 34, Issue 15, 2004, Pages 2719-2735

Friedel-crafts reaction of activated benzene rings with captodative and electron-deficient alkenes. A one-step synthesis of the natural product methyl 3-(2,4,5-trimethoxyphenyl)propionate

Author keywords

Captodative olefins; Friedel Crafts; Methyl 3 (2,4,5 trimethoxyphenyl) propionate

Indexed keywords

1 ACETYLVINYL 1,4 NITROBENZOATE; 1,2,4 TRIMETHOXYBENZENE; ACROLEIN; ACRYLIC ACID METHYL ESTER; ALKENE; ALKENE DERIVATIVE; ANTIFUNGAL AGENT; AROMATIC COMPOUND; BENZENE; BENZENE DERIVATIVE; KETONE DERIVATIVE; LARVICIDAL AGENT; LEWIS ACID; METHYL 3 (2,4,5 TRIMETHOXYPHENYL)PROPIONATE; METHYLVINYLKETONE; NITROBENZOIC ACID DERIVATIVE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 4444282581     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200026193     Document Type: Article
Times cited : (17)

References (69)
  • 1
    • 0037321888 scopus 로고    scopus 로고
    • The biosynthesis of shikimate metabolites
    • (a) Knaggs, A.R. The biosynthesis of shikimate metabolites. Nat. Prod. Rep. 2003, 20, 119-136;
    • (2003) Nat. Prod. Rep. , vol.20 , pp. 119-136
    • Knaggs, A.R.1
  • 2
    • 0242500948 scopus 로고    scopus 로고
    • Structure-antioxidant activity relationship of ferulic acid derivatives: Effect of carbon side chain characteristic groups
    • (b) Nenadis, N.; Zhang, H.-Y.; Tsimidou, M.Z.J. Structure-antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups. J. Agric. Food Chem. 2003, 51, 1874-1879.
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 1874-1879
    • Nenadis, N.1    Zhang, H.-Y.2    Tsimidou, M.Z.J.3
  • 4
    • 0032720664 scopus 로고    scopus 로고
    • Novel aspects of tannins - Renewed concepts and structure-activity relationships
    • (b) Okuda, T. Novel aspects of tannins - renewed concepts and structure-activity relationships. Curr. Org. Chem. 1999, 3, 609-622.
    • (1999) Curr. Org. Chem. , vol.3 , pp. 609-622
    • Okuda, T.1
  • 5
    • 0032739997 scopus 로고    scopus 로고
    • Isoferulic acid as active principle from the rhizoma of Cimicifuga dahurica to lower plasma glucose in diabetic rats
    • (a) Liu, I.-M.; Chi, T.-C.; Hsu, F.-L.; Chen, C.-F.; Cheng, J.-T. Isoferulic acid as active principle from the rhizoma of Cimicifuga dahurica to lower plasma glucose in diabetic rats. Planta Med. 1999, 65, 712-714;
    • (1999) Planta Med. , vol.65 , pp. 712-714
    • Liu, I.-M.1    Chi, T.-C.2    Hsu, F.-L.3    Chen, C.-F.4    Cheng, J.-T.5
  • 6
    • 0037048724 scopus 로고    scopus 로고
    • Peroxynitrite scavenging activity of sinapic acid (3,5-dimethoxy-4- hydroxycinnamic acid) isolated from Brassica juncea
    • (b) Zou, Y.; Kim, A.R.; Kim, J.E.; Choi, J.S.; Chung, H.Y. Peroxynitrite scavenging activity of sinapic acid (3,5-dimethoxy-4-hydroxycinnamic acid) isolated from Brassica juncea. J. Agric. Food Chem. 2002, 50, 5884-5890;
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 5884-5890
    • Zou, Y.1    Kim, A.R.2    Kim, J.E.3    Choi, J.S.4    Chung, H.Y.5
  • 7
    • 0037467073 scopus 로고    scopus 로고
    • Effects of phenolic acids on human phenol sulfotransferases in relation to their antioxidant activity
    • (c) Yeh, C.-T.; Yen, G.-C. Effects of phenolic acids on human phenol sulfotransferases in relation to their antioxidant activity. J. Agric. Food Chem. 2003, 51, 1474-1479.
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 1474-1479
    • Yeh, C.-T.1    Yen, G.-C.2
  • 8
    • 0032713589 scopus 로고    scopus 로고
    • Developmental changes in cell-wall ferulate and dehydrodiferulates in sugar beet
    • (a) Wende, G.; Waldron, K.W.; Smith, A.C.; Brett, C.T. Developmental changes in cell-wall ferulate and dehydrodiferulates in sugar beet. Phytochemistry 1999, 52, 819-827;
    • (1999) Phytochemistry , vol.52 , pp. 819-827
    • Wende, G.1    Waldron, K.W.2    Smith, A.C.3    Brett, C.T.4
  • 9
    • 0037063393 scopus 로고    scopus 로고
    • Antioxidant activities and phenolic composition of extracts from Greek oregano, Greek sage, and summer savory
    • (b) Exarchou, V.; Nenadis, N.; Tsimidou, M.; Gerothanassis, I.P.; Troganis, A.; Boskou, D. Antioxidant activities and phenolic composition of extracts from Greek oregano, Greek sage, and summer savory. J. Agric. Food Chem. 2002, 50, 5294-5299;
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 5294-5299
    • Exarchou, V.1    Nenadis, N.2    Tsimidou, M.3    Gerothanassis, I.P.4    Troganis, A.5    Boskou, D.6
  • 10
    • 0034850886 scopus 로고    scopus 로고
    • Antioxidant effects of phenolic rye (Secale cereale L.) extracts, monomeric hydroxycinnamates, and ferulic acid dehydrodimers on human low-density lipoproteins
    • (c) Andreasen, M.F.; Landbo, A.-K.; Christensen, L.P.; Hansen, A.; Meyer, A.S. Antioxidant effects of phenolic rye (Secale cereale L.) extracts, monomeric hydroxycinnamates, and ferulic acid dehydrodimers on human low-density lipoproteins. J. Agric. Food Chem. 2001, 49, 4090-4096;
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 4090-4096
    • Andreasen, M.F.1    Landbo, A.-K.2    Christensen, L.P.3    Hansen, A.4    Meyer, A.S.5
  • 11
    • 0037048762 scopus 로고    scopus 로고
    • Model studies of ferulate-coniferyl alcohol cross-product formation in primary maize walls: Implications for lignification in grasses
    • (d) Grabber, J.H.; Ralph, J.; Hatfield, R.D. Model studies of ferulate-coniferyl alcohol cross-product formation in primary maize walls: implications for lignification in grasses. J. Agric. Food Chem. 2002, 50, 6008-6016.
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 6008-6016
    • Grabber, J.H.1    Ralph, J.2    Hatfield, R.D.3
  • 12
    • 0036973247 scopus 로고    scopus 로고
    • Study on the multiple mechanisms underlying the reaction between hydroxyl radical and phenolic compounds by qualitative structure and activity relationship
    • (a) Cheng, Z.; Ren, J.; Li, Y.; Chang, W.; Chen, Z. Study on the multiple mechanisms underlying the reaction between hydroxyl radical and phenolic compounds by qualitative structure and activity relationship. Bioorg. Med. Chem. 2002, 10, 4067-4073;
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 4067-4073
    • Cheng, Z.1    Ren, J.2    Li, Y.3    Chang, W.4    Chen, Z.5
  • 14
    • 0037070326 scopus 로고    scopus 로고
    • Tyrosinase inhibitors of Pulsatilla cernva root-derived materials
    • and references cited therein
    • (c) Lee, H.-S. Tyrosinase inhibitors of Pulsatilla cernva root-derived materials. J. Agric. Food Chem. 2002, 50, 1400-1403, and references cited therein;
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 1400-1403
    • Lee, H.-S.1
  • 15
    • 0035192121 scopus 로고    scopus 로고
    • Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids
    • (d) Etzenhouser, B.; Hansch, C.; Kapur, S.; Selassie, C.D. Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids. Bioorg. Med. Chem. 2001, 9, 199-209;
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 199-209
    • Etzenhouser, B.1    Hansch, C.2    Kapur, S.3    Selassie, C.D.4
  • 16
    • 0018875869 scopus 로고
    • Studies on antihyperlipidemic agents. II. Synthesis and biological activities of 2-chloro-3-arylpropionic acids
    • (e) Kawamatsu, Y.; Asakawa, H.; Saraie, T.; Imamiya, E.; Nishikawa, K.; Hamuro, Y. Studies on antihyperlipidemic agents. II. Synthesis and biological activities of 2-chloro-3-arylpropionic acids. Arzneim.-Forsch. 1980, 30, 585-589;
    • (1980) Arzneim.-Forsch. , vol.30 , pp. 585-589
    • Kawamatsu, Y.1    Asakawa, H.2    Saraie, T.3    Imamiya, E.4    Nishikawa, K.5    Hamuro, Y.6
  • 17
    • 0033619997 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit Tubulin polymerization
    • (f) Pieters, L.; Van Dyck, S.; Gao, M.; Bai, R.; Hamel, E.; Vlietinck, A.; Lemiére, G. Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit Tubulin polymerization. J. Med. Chem. 1999, 42, 5475-5481;
    • (1999) J. Med. Chem. , vol.42 , pp. 5475-5481
    • Pieters, L.1    Van Dyck, S.2    Gao, M.3    Bai, R.4    Hamel, E.5    Vlietinck, A.6    Lemiére, G.7
  • 19
    • 0034524722 scopus 로고    scopus 로고
    • Cross-linking of maize walls by ferulate dimerization and incorporation into lignin
    • (a) Grabber, J.H.; Ralph, J.; Hatfield, R.D. Cross-linking of maize walls by ferulate dimerization and incorporation into lignin. J. Agric. Food Chem. 2000, 48, 6106-6113;
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 6106-6113
    • Grabber, J.H.1    Ralph, J.2    Hatfield, R.D.3
  • 20
    • 0035200186 scopus 로고    scopus 로고
    • Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed
    • (b) Ford, J.D.; Huang, K.-S.; Wang, H.-B.; Davin, L.B.; Lewis, N.G. Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed. J. Nat. Prod. 2001, 64, 1388-1397;
    • (2001) J. Nat. Prod. , vol.64 , pp. 1388-1397
    • Ford, J.D.1    Huang, K.-S.2    Wang, H.-B.3    Davin, L.B.4    Lewis, N.G.5
  • 21
    • 0037181286 scopus 로고    scopus 로고
    • Effects of commercial processing on levels of antioxidants in oats (Avena sativa L.)
    • (c) Bryngelsson, S.; Dimberg, L.H.; Kamal-Eldin, A. Effects of commercial processing on levels of antioxidants in oats (Avena sativa L.). J. Agric. Food Chem. 2002, 50, 1890-1896;
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 1890-1896
    • Bryngelsson, S.1    Dimberg, L.H.2    Kamal-Eldin, A.3
  • 22
    • 0036271131 scopus 로고    scopus 로고
    • 4-induced toxicity: Action mechanism and structure-activity relationship
    • 4-induced toxicity: action mechanism and structure-activity relationship. Planta Med. 2002, 68, 407-411;
    • (2002) Planta Med. , vol.68 , pp. 407-411
    • Lee, E.J.1    Kim, S.R.2    Kim, J.3    Kim, Y.C.4
  • 23
    • 0032933519 scopus 로고    scopus 로고
    • C- and O-glycosyl-α-hydrodihydrochalcones from Eysenhardtia polistachya
    • (e) Alvarez, L.; Delgado, G. C- and O-glycosyl-α- hydrodihydrochalcones from Eysenhardtia polistachya. Phytochemistry 1999, 50, 681-687;
    • (1999) Phytochemistry , vol.50 , pp. 681-687
    • Alvarez, L.1    Delgado, G.2
  • 24
    • 0037433525 scopus 로고    scopus 로고
    • High-performance liquid chromatography determination of phenolic constituents in 17 varieties of cowpeas
    • (f) Cai, R.; Hettiarachchy, N.S.; Jalaluddin, M. High-performance liquid chromatography determination of phenolic constituents in 17 varieties of cowpeas. J. Agric. Food Chem. 2003, 51, 1623-1627.
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 1623-1627
    • Cai, R.1    Hettiarachchy, N.S.2    Jalaluddin, M.3
  • 26
    • 0034847017 scopus 로고    scopus 로고
    • Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity
    • (b) Baderschneider, B.; Winterhalter, P. Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity. J. Agric. Food Chem. 2001, 49, 2788-2798;
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 2788-2798
    • Baderschneider, B.1    Winterhalter, P.2
  • 27
    • 0034838413 scopus 로고    scopus 로고
    • Effects of phenolic propyl esters on the oxidative stability of refined sunflower oil
    • (c) Silva, F.A.M.; Borges, F.; Ferreira, M.A. Effects of phenolic propyl esters on the oxidative stability of refined sunflower oil. J. Agric. Food Chem. 2001, 49, 3936-3941.
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 3936-3941
    • Silva, F.A.M.1    Borges, F.2    Ferreira, M.A.3
  • 28
    • 0034117969 scopus 로고    scopus 로고
    • Antifungal and larvicidal compounds from the root bark of Cordia alliodora
    • Ioset, J.-R.; Marston, A.; Gupta, M.P.; Hostettmann, K. Antifungal and larvicidal compounds from the root bark of Cordia alliodora. J. Nat. Prod. 2000, 63, 424-426.
    • (2000) J. Nat. Prod. , vol.63 , pp. 424-426
    • Ioset, J.-R.1    Marston, A.2    Gupta, M.P.3    Hostettmann, K.4
  • 29
    • 0000248247 scopus 로고
    • The Knoevenagel condensation
    • (a) Jones, G. The Knoevenagel condensation. Org. React. 1967, 15, 204-599;
    • (1967) Org. React. , vol.15 , pp. 204-599
    • Jones, G.1
  • 30
    • 10644268419 scopus 로고
    • Electronic effects in homogeneous indenylzirconium Ziegler-Natta catalysts
    • (b) Piccolrovazzi, N.; Pino, P.; Consiglio, G.; Sironi, A.; Moret, M. Electronic effects in homogeneous indenylzirconium Ziegler-Natta catalysts. Organometallics 1990, 9, 3098-3105;
    • (1990) Organometallics , vol.9 , pp. 3098-3105
    • Piccolrovazzi, N.1    Pino, P.2    Consiglio, G.3    Sironi, A.4    Moret, M.5
  • 31
    • 0028848088 scopus 로고
    • Knoevenagel condensation catalyzed by a Mexican bentonite using infrared irradiation
    • (c) Delgado, F.; Tamariz, J.; Zepeda, G.; Landa, M.; Miranda, R.; García, J. Knoevenagel condensation catalyzed by a Mexican bentonite using infrared irradiation. Synth. Commun. 1995, 25, 753-759;
    • (1995) Synth. Commun. , vol.25 , pp. 753-759
    • Delgado, F.1    Tamariz, J.2    Zepeda, G.3    Landa, M.4    Miranda, R.5    García, J.6
  • 32
    • 0037220240 scopus 로고    scopus 로고
    • An improved synthesis of (E)-cinnamic acid derivatives via the Claisen-Schmidt condensation
    • (d) Hatsuda, M.; Kuroda, T.; Seki, M. An improved synthesis of (E)-cinnamic acid derivatives via the Claisen-Schmidt condensation. Synth. Commun. 2003, 33, 427-434.
    • (2003) Synth. Commun. , vol.33 , pp. 427-434
    • Hatsuda, M.1    Kuroda, T.2    Seki, M.3
  • 33
    • 0034894889 scopus 로고    scopus 로고
    • A comparative study of some Pd-catalysed Heck reactions in polar- and aqueous biphasic media
    • (a) Williams, D.B.G.; Lombard, H.; Holzapfel, C.W. A comparative study of some Pd-catalysed Heck reactions in polar- and aqueous biphasic media. Synth. Commun. 2001, 31, 2077-2081;
    • (2001) Synth. Commun. , vol.31 , pp. 2077-2081
    • Williams, D.B.G.1    Lombard, H.2    Holzapfel, C.W.3
  • 34
    • 0032760634 scopus 로고    scopus 로고
    • A practical and cost-effective synthesis of 6,7-dimethoxy-2-tetralone
    • (b) Qandil, A.M.; Miller, D.W.; Nichols, D.E. A practical and cost-effective synthesis of 6,7-dimethoxy-2-tetralone. Synthesis 1999, 2033-2035;
    • (1999) Synthesis , pp. 2033-2035
    • Qandil, A.M.1    Miller, D.W.2    Nichols, D.E.3
  • 35
    • 0037162759 scopus 로고    scopus 로고
    • High-speed Heck reactions in ionic liquid with controlled microwave heating
    • (c) Vallin, K.S.A.; Emilsson, P.; Larhed, M.; Hallberg, A. High-speed Heck reactions in ionic liquid with controlled microwave heating. J. Org. Chem. 2002, 67, 6243-6246;
    • (2002) J. Org. Chem. , vol.67 , pp. 6243-6246
    • Vallin, K.S.A.1    Emilsson, P.2    Larhed, M.3    Hallberg, A.4
  • 36
    • 0000702671 scopus 로고
    • Palladium-catalyzed vinylation of organic halides
    • (d) Heck, R.F. Palladium-catalyzed vinylation of organic halides. Org. React. 1982, 27, 345-390.
    • (1982) Org. React. , vol.27 , pp. 345-390
    • Heck, R.F.1
  • 39
    • 0000220284 scopus 로고
    • Organocopper reagents: Substitution, conjugate addition, carbo/metallocupration, and other reactions
    • (c) Lipshutz, B.H.; Sengupta, S. Organocopper reagents: substitution, conjugate addition, carbo/metallocupration, and other reactions. Org. React. 1992, 41, 135-631.
    • (1992) Org. React. , vol.41 , pp. 135-631
    • Lipshutz, B.H.1    Sengupta, S.2
  • 40
    • 0001586671 scopus 로고
    • Friedel-Crafts alkylations
    • Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford
    • (a) Olah, G.A.; Krishnamurti, R.; Prakash, G.K.S. Friedel-Crafts alkylations. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, 293-339;
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 293-339
    • Olah, G.A.1    Krishnamurti, R.2    Prakash, G.K.S.3
  • 41
    • 0001759458 scopus 로고    scopus 로고
    • Detailed characterization of p-toluenesulfonic acid monohydrate as a convenient, recoverable, safe, and selective catalyst for alkylation of the aromatic nucleus
    • (b) Mahindaratne, M.P.D.; Wimalasena, K. Detailed characterization of p-toluenesulfonic acid monohydrate as a convenient, recoverable, safe, and selective catalyst for alkylation of the aromatic nucleus. J. Org. Chem. 1998, 63, 2858-2866.
    • (1998) J. Org. Chem. , vol.63 , pp. 2858-2866
    • Mahindaratne, M.P.D.1    Wimalasena, K.2
  • 42
    • 0001123875 scopus 로고
    • The first Friedel-Crafts reaction of nitrobenzene
    • (a) Shen, Y.-s.S.; Liu, H.-x.; Chen, Y.-q. The first Friedel-Crafts reaction of nitrobenzene. J. Org. Chem. 1990, 55, 3961-3962;
    • (1990) J. Org. Chem. , vol.55 , pp. 3961-3962
    • Shen, Y.-S.S.1    Liu, H.-X.2    Chen, Y.-Q.3
  • 43
    • 4444223132 scopus 로고
    • Amberlyst-15 catalyzed addition of phenols to α,β-unsaturated ketones
    • (b) Bunce, R.A.; Reeves, H.D. Amberlyst-15 catalyzed addition of phenols to α,β-unsaturated ketones. Synth. Commun. 1989, 19, 1109-1117;
    • (1989) Synth. Commun. , vol.19 , pp. 1109-1117
    • Bunce, R.A.1    Reeves, H.D.2
  • 45
    • 0035825178 scopus 로고    scopus 로고
    • Catalytic asymmetric Friedel-Crafts alkylation of β,γ- unsaturated α-ketoesters: Enantioselective addition of aromatic C-H bonds to alkenes
    • (d) Jensen, K.B.; Thorhauge, J.; Hazell, R.G.; Jørgensen, K.A. Catalytic asymmetric Friedel-Crafts alkylation of β,γ-unsaturated α-ketoesters: enantioselective addition of aromatic C-H bonds to alkenes. Angew. Chem., Int. Ed. 2001, 40, 160-163;
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 160-163
    • Jensen, K.B.1    Thorhauge, J.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 46
    • 0000432095 scopus 로고
    • Cation-exchanged montmorillonite-catalyzed facile Friedel-Crafts alkylation of hydroxy and methoxy aromatics with 4-hydroxybutan-2-ones to produce rasberry ketone and some pharmaceutically active compounds
    • (e) Tateiwa, J.-I.; Horiuchi, H.; Hashimoto, K.; Yamauchi, T.; Uemura, S. Cation-exchanged montmorillonite-catalyzed facile Friedel-Crafts alkylation of hydroxy and methoxy aromatics with 4-hydroxybutan-2-ones to produce rasberry ketone and some pharmaceutically active compounds. J. Org. Chem. 1994, 59, 5901-5904.
    • (1994) J. Org. Chem. , vol.59 , pp. 5901-5904
    • Tateiwa, J.-I.1    Horiuchi, H.2    Hashimoto, K.3    Yamauchi, T.4    Uemura, S.5
  • 47
    • 0025343348 scopus 로고
    • Highly selective Diels-Alder cycloadditions of captodative dienophiles 1-acetylvinyl arenecarboxylates to unsymmetrically substituted butadienes
    • (a) Reyes, A.; Aguilar, R.; Muñoz, A.H.; Zwick, J.-C.; Rubio, M.; Escobar, J.-L.; Soriano, M.; Toscano, R.; Tamariz, J. Highly selective Diels-Alder cycloadditions of captodative dienophiles 1-acetylvinyl arenecarboxylates to unsymmetrically substituted butadienes. J. Org. Chem. 1990, 55, 1024-1034;
    • (1990) J. Org. Chem. , vol.55 , pp. 1024-1034
    • Reyes, A.1    Aguilar, R.2    Muñoz, A.H.3    Zwick, J.-C.4    Rubio, M.5    Escobar, J.-L.6    Soriano, M.7    Toscano, R.8    Tamariz, J.9
  • 48
    • 0028964197 scopus 로고
    • Stereoselective synthesis, NMR conformational study and Diels-Alder reaction of β-functionalized 1-acetylvinyl arenecarboxylates
    • (b) Peralta, J.; Bullock, J.P.; Bates, R.W.; Bott, S.; Zepeda, G.; Tamariz, J. Stereoselective synthesis, NMR conformational study and Diels-Alder reaction of β-functionalized 1-acetylvinyl arenecarboxylates. Tetrahedron 1995, 51, 3979-3996;
    • (1995) Tetrahedron , vol.51 , pp. 3979-3996
    • Peralta, J.1    Bullock, J.P.2    Bates, R.W.3    Bott, S.4    Zepeda, G.5    Tamariz, J.6
  • 49
    • 0033579632 scopus 로고    scopus 로고
    • Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one as a Diels-Alder ketene equivalent for the synthesis of γ-hydroxycyclohexenones
    • (c) Ochoa, M.E.; Arias, A.S.; Aguilar, R.; Delgado, F.; Tamariz, J. Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one as a Diels-Alder ketene equivalent for the synthesis of γ-hydroxycyclohexenones. Tetrahedron 1999, 55, 14535-14546;
    • (1999) Tetrahedron , vol.55 , pp. 14535-14546
    • Ochoa, M.E.1    Arias, A.S.2    Aguilar, R.3    Delgado, F.4    Tamariz, J.5
  • 50
    • 0035936770 scopus 로고    scopus 로고
    • Regio-and stereoselectivity of captodative olefins in 1,3-dipolar cycloadditions. A DFT/HSAB theory rationale for the observed regiochemistry of nitrones
    • (d) Herrera, R.; Nagarajan, A.; Morales, M.A.; Méndez, F.; Jiménez-Vázquez, H.A.; Zepeda, G.; Tamariz, J. Regio-and stereoselectivity of captodative olefins in 1,3-dipolar cycloadditions. A DFT/HSAB theory rationale for the observed regiochemistry of nitrones. J. Org. Chem. 2001, 66, 1252-1263.
    • (2001) J. Org. Chem. , vol.66 , pp. 1252-1263
    • Herrera, R.1    Nagarajan, A.2    Morales, M.A.3    Méndez, F.4    Jiménez-Vázquez, H.A.5    Zepeda, G.6    Tamariz, J.7
  • 54
    • 33947465158 scopus 로고
    • Cyanoethylation of phenol; isolation of an ortho-addition product
    • Johnston, H.W.; Gross, F.J. Cyanoethylation of phenol; isolation of an ortho-addition product. J. Org. Chem. 1957, 22, 1264-1265.
    • (1957) J. Org. Chem. , vol.22 , pp. 1264-1265
    • Johnston, H.W.1    Gross, F.J.2
  • 55
    • 4444280029 scopus 로고
    • Carbon-carbon cyanoethylation of anisole and its derivatives
    • Chatterjee, A.; Hazra, B.G. Carbon-carbon cyanoethylation of anisole and its derivatives. Tetrahedron 1977, 33, 1983-1987.
    • (1977) Tetrahedron , vol.33 , pp. 1983-1987
    • Chatterjee, A.1    Hazra, B.G.2
  • 56
    • 0029163368 scopus 로고
    • Titanium tetrachloride-mediated carbon-carbon chlorocyanoethylation of anisole: Synthesis of tyrosine derivatives
    • Hazra, B.G.; Pore, V.S.; Basu, S. Titanium tetrachloride-mediated carbon-carbon chlorocyanoethylation of anisole: synthesis of tyrosine derivatives. Synthetic Commun. 1995, 25, 2847-2855.
    • (1995) Synthetic Commun. , vol.25 , pp. 2847-2855
    • Hazra, B.G.1    Pore, V.S.2    Basu, S.3
  • 57
    • 33947454726 scopus 로고
    • Vinylidene cyanide. V. The aluminum chloride catalyzed reaction of vinylidene cyanide and aromatic compounds
    • Westfahl, L.; Gresham, T.L. Vinylidene cyanide. V. The aluminum chloride catalyzed reaction of vinylidene cyanide and aromatic compounds. J. Am. Chem. Soc. 1954, 76, 1076-1080.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 1076-1080
    • Westfahl, L.1    Gresham, T.L.2
  • 58
    • 0342656158 scopus 로고    scopus 로고
    • Regioselective synthesis of N-substituted 4-methylene-2-oxazolidinones and 4-oxazolin-2-ones. Study of reactivity in thermal Michael conjugate additions
    • Martínez, R.; Jiménez-Vázquez, H.A.; Tamariz, J. Regioselective synthesis of N-substituted 4-methylene-2-oxazolidinones and 4-oxazolin-2-ones. Study of reactivity in thermal Michael conjugate additions. Tetrahedron 2000, 56, 3857-3866.
    • (2000) Tetrahedron , vol.56 , pp. 3857-3866
    • Martínez, R.1    Jiménez-Vázquez, H.A.2    Tamariz, J.3
  • 59
    • 4444240444 scopus 로고
    • Phosphorus acids in organic systems. III. Specific pyrophosphoric acid catalysis in the conversion of resorcinol dimethyl ether to coumarins
    • Narayana, M.; Dash, J.F.; Gardner, P.D. Phosphorus acids in organic systems. III. Specific pyrophosphoric acid catalysis in the conversion of resorcinol dimethyl ether to coumarins. J. Org. Chem. 1962, 27, 4704-4705.
    • (1962) J. Org. Chem. , vol.27 , pp. 4704-4705
    • Narayana, M.1    Dash, J.F.2    Gardner, P.D.3
  • 60
    • 0027749566 scopus 로고
    • Farmacología y toxicología de Guatteria gaumeri y α-asarona
    • and references cited therein
    • (a) Chamorro, G.; Salazar, M.; Salazar, S.; Mendoza, T. Farmacología y toxicología de Guatteria gaumeri y α-asarona. Rev. Inv. Clin. 1993, 45, 597-604, and references cited therein;
    • (1993) Rev. Inv. Clin. , vol.45 , pp. 597-604
    • Chamorro, G.1    Salazar, M.2    Salazar, S.3    Mendoza, T.4
  • 61
    • 0020576244 scopus 로고
    • Mutagenicity testing of β-asarone and commercial calamus drugs with Salmonella typhimurium
    • (b) Göggelmann, W.; Schimmer, O. Mutagenicity testing of β-asarone and commercial calamus drugs with Salmonella typhimurium. Mutation Res. 1983, 121, 191-194;
    • (1983) Mutation Res. , vol.121 , pp. 191-194
    • Göggelmann, W.1    Schimmer, O.2
  • 62
    • 0023359755 scopus 로고
    • Chromosomenschädigende wirkung von β-asaron in menschlichen lymphocyten
    • (c) Abel, G. Chromosomenschädigende wirkung von β-asaron in menschlichen lymphocyten. Planta Med. 1987, 53, 251-253.
    • (1987) Planta Med. , vol.53 , pp. 251-253
    • Abel, G.1
  • 63
    • 0036225660 scopus 로고    scopus 로고
    • A concise conversion of β-asarone to 1-(2-carbomethoxyethyl)-2,4,5- trimethoxybenzene occurring in Cordia alliodora
    • Section B
    • (a) Sinha, A.K.; Dogra, R.; Joshi, B.P. A concise conversion of β-asarone to 1-(2-carbomethoxyethyl)-2,4,5-trimethoxybenzene occurring in Cordia alliodora. Ind. J. Chem. 2002, 41B, 635-638; Section B;
    • (2002) Ind. J. Chem. , vol.41 B , pp. 635-638
    • Sinha, A.K.1    Dogra, R.2    Joshi, B.P.3
  • 64
    • 0036320254 scopus 로고    scopus 로고
    • Synthesis of methyl 3-(2,4,5-trimethoxyphenyl)propionate, an antifungal and larvicidal constituent of Cordia alliodora
    • (b) Vanisree, M.; Kavitha, J.; Subbaraju, G.V. Synthesis of methyl 3-(2,4,5-trimethoxyphenyl)propionate, an antifungal and larvicidal constituent of Cordia alliodora. Asian J. Chem. 2002, 14, 534-536.
    • (2002) Asian J. Chem. , vol.14 , pp. 534-536
    • Vanisree, M.1    Kavitha, J.2    Subbaraju, G.V.3
  • 66
    • 0031355495 scopus 로고    scopus 로고
    • Structural, spectroscopic, and theoretical study of 1-acetylvinyl p-nitrobenzoate, a highly reactive and selective captodative olefin in cycloaddition reactions
    • (a) Jiménez-Vázquez, H.A.; Ochoa, M.E.; Zepeda, G.; Modelli, A.; Jones, D.; Mendoza, J.A.; Tamariz, J. Structural, spectroscopic, and theoretical study of 1-acetylvinyl p-nitrobenzoate, a highly reactive and selective captodative olefin in cycloaddition reactions. J. Phys. Chem. A 1997, 101, 10082-10089;
    • (1997) J. Phys. Chem. A , vol.101 , pp. 10082-10089
    • Jiménez-Vázquez, H.A.1    Ochoa, M.E.2    Zepeda, G.3    Modelli, A.4    Jones, D.5    Mendoza, J.A.6    Tamariz, J.7
  • 67
    • 0035667957 scopus 로고    scopus 로고
    • Synthesis of new captodative alkenes: Alkyl 2-aroyloxy acrylates - Structure, and reactivity in Diels-Alder cycloadditions
    • (b) Herrera, R.; Jiménez-Vázquez, H.A.; Modelli, A.; Jones, D.; Söderberg, B.C.; Tamariz, J. Synthesis of new captodative alkenes: alkyl 2-aroyloxy acrylates - structure, and reactivity in Diels-Alder cycloadditions. Eur. J. Org. Chem. 2001, 4657-4669.
    • (2001) Eur. J. Org. Chem. , pp. 4657-4669
    • Herrera, R.1    Jiménez-Vázquez, H.A.2    Modelli, A.3    Jones, D.4    Söderberg, B.C.5    Tamariz, J.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.