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Volumn 38, Issue 20, 2008, Pages 3398-3405

Efficient one-pot synthesis of the GABAB positive allosteric modulator (R,S)-5,7-Di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2- one

Author keywords

(R,S) 5,7 Di tert butyl 3 hydroxy 3 trifluoromethyl 3H benzofuran 2 one; GABAB positive allosteric modulator; Gallium(III) chloride; One pot synthesis

Indexed keywords

2 (3,5 DI TERT BUTYL 2 HYDROXYPHENYL) 3,3,3 TRIFLUORO 2 HYDROXY PROPIONIC ACID; 4 AMINOBUTYRIC ACID; 5 (3,5 DI TERT BUTYL 2 HYDROXYPHENYL) 3 ( 1 NAPTHALEN 1 YLETHYL) 5 TRIFLUOROMETHYLOXAZOLIDINE 2,4 DIONE; 5,7 DI TERT BUTYL 3 HYDROXY 3 TRIFLUOROMETHYL 3H BENZOFURAN 2 ONE; BENZOFURAN DERIVATIVE; GALLIUM CHLORIDE; LACTONE; LEWIS ACID; LITHIUM SALT; PHENOL DERIVATIVE; PYRUVIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 53149100874     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801979403     Document Type: Article
Times cited : (9)

References (13)
  • 1
    • 53149123774 scopus 로고    scopus 로고
    • B receptor modulators for treating CNS disorders. U.S. Patent 2,007,027,204, 2007; Chem. Abstr. 2007, 146, 184345.
    • B receptor modulators for treating CNS disorders. U.S. Patent 2,007,027,204, 2007; Chem. Abstr. 2007, 146, 184345.
  • 3
    • 37049105948 scopus 로고
    • Unusual Friedel-Crafts reactions, part 7: Synthesis of a-(2-hydroxyphenyl)ethyl lactates and their reductive cyclization to 3-methyl-2,3-dihydrobenzofuran-2-ols
    • Casiraghi, G.; Sartori, G.; Casnati, G.; Bigi, F. Unusual Friedel-Crafts reactions, part 7: Synthesis of a-(2-hydroxyphenyl)ethyl lactates and their reductive cyclization to 3-methyl-2,3-dihydrobenzofuran-2-ols. J. Chem. Soc. Perkin Trans 1 1983, 1649-1651.
    • (1983) J. Chem. Soc. Perkin Trans 1 , pp. 1649-1651
    • Casiraghi, G.1    Sartori, G.2    Casnati, G.3    Bigi, F.4
  • 5
    • 0035830539 scopus 로고    scopus 로고
    • Catalytic, highly enantioselective Friedel-Crafts reactions of aromatic and heteroaromatic compounds to trifluoropyruvate: A simple approach for the formation of optically active aromatic and heteroaromatic hydroxy trifluoromethyl esters
    • Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jorgensen, K. A. Catalytic, highly enantioselective Friedel-Crafts reactions of aromatic and heteroaromatic compounds to trifluoropyruvate: A simple approach for the formation of optically active aromatic and heteroaromatic hydroxy trifluoromethyl esters. J. Org. Chem. 2001, 66, 1009-1013.
    • (2001) J. Org. Chem , vol.66 , pp. 1009-1013
    • Zhuang, W.1    Gathergood, N.2    Hazell, R.G.3    Jorgensen, K.A.4
  • 6
    • 0037232079 scopus 로고    scopus 로고
    • Superacid catalyzed hydroxyalkylation of aromatics with ethyl trifluoropyruvate: A new synthetic route to Mosher's acid analogs
    • Prakash, G. K. S.; Yan, P.; Torok, B.; Olah, G. A. Superacid catalyzed hydroxyalkylation of aromatics with ethyl trifluoropyruvate: A new synthetic route to Mosher's acid analogs. Synthesis 2003, 527-531.
    • (2003) Synthesis , pp. 527-531
    • Prakash, G.K.S.1    Yan, P.2    Torok, B.3    Olah, G.A.4
  • 7
    • 1442335538 scopus 로고    scopus 로고
    • In(OTf)3-catalyzed Friedel-Crafts reaction of aromatic compounds with methyl trifluoropyruvate in water
    • Ding, R.; Zhang, H. B.; Chen, Y. J.; Liu, L.; Wang, D.; Li, C. J. In(OTf)3-catalyzed Friedel-Crafts reaction of aromatic compounds with methyl trifluoropyruvate in water. Synthesis 2004, 555-557.
    • (2004) Synthesis , pp. 555-557
    • Ding, R.1    Zhang, H.B.2    Chen, Y.J.3    Liu, L.4    Wang, D.5    Li, C.J.6
  • 8
    • 9944228606 scopus 로고    scopus 로고
    • Enantioselective catalysis of carbonyl-ene and Friedel-Crafts reactions with trifluoropyruvate by 'naked' palladium(II) complexes with SEGPHOS ligands
    • Mikami, K.; Aikawa, K.; Kainuma, S.; Kawakami, Y.; Saito, T.; Sayo, N.; Kumobayashi, H. Enantioselective catalysis of carbonyl-ene and Friedel-Crafts reactions with trifluoropyruvate by 'naked' palladium(II) complexes with SEGPHOS ligands. Tetrahedron: Asymmetry. 2004,15, 3885-3889.
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 3885-3889
    • Mikami, K.1    Aikawa, K.2    Kainuma, S.3    Kawakami, Y.4    Saito, T.5    Sayo, N.6    Kumobayashi, H.7
  • 9
    • 0028001232 scopus 로고
    • In situ NMR spectroscopic studies of aniline ortho acylation ("Sugasawa reaction"): The nature of reaction intermediates and Lewis acid influence on yield
    • Douglas, A. W.; Abramson, N. L.; Houpis, I. N.; Karady, S.; Molina, A.; Xavier, L. C.; Yasuda, N. In situ NMR spectroscopic studies of aniline ortho acylation ("Sugasawa reaction"): The nature of reaction intermediates and Lewis acid influence on yield. Tetrahedron Lett. 1994, 35, 6807-6810.
    • (1994) Tetrahedron Lett , vol.35 , pp. 6807-6810
    • Douglas, A.W.1    Abramson, N.L.2    Houpis, I.N.3    Karady, S.4    Molina, A.5    Xavier, L.C.6    Yasuda, N.7
  • 11
    • 84988116315 scopus 로고
    • Titanium tetrachloride induced Fries rearrangement: A new route to disubstituted 2′-hydroxypropiophenones
    • Martin, R.; Demerseman, P. Titanium tetrachloride induced Fries rearrangement: A new route to disubstituted 2′-hydroxypropiophenones. Synthesis 1989, 25-28.
    • (1989) Synthesis , pp. 25-28
    • Martin, R.1    Demerseman, P.2
  • 12
    • 53149151189 scopus 로고
    • Preparation of anhydrous organic acid salts
    • U.S. Patent 4723016, 189841
    • Chenard, B. L.; Laganis, E. D. Preparation of anhydrous organic acid salts. U.S. Patent 4723016, 1988; Chem. Abstr. 1988, 109, 189841.
    • (1988) Chem. Abstr , vol.109
    • Chenard, B.L.1    Laganis, E.D.2
  • 13
    • 2342634439 scopus 로고    scopus 로고
    • Thorpe-Ingold effects in cyclizations to five-membered and six-membered rings containing planar segments: The rearrangement of N(1)-alkyl-substituted dihydroorotic acids to hydantoinacetic acids in base
    • Kaneti, J.; Kirby, A. J.; Koedjikov, A. H.; Pojarlieff, I. G. Thorpe-Ingold effects in cyclizations to five-membered and six-membered rings containing planar segments: The rearrangement of N(1)-alkyl-substituted dihydroorotic acids to hydantoinacetic acids in base. Org. Biomol. Chem. 2004, 2, 1098-1103.
    • (2004) Org. Biomol. Chem , vol.2 , pp. 1098-1103
    • Kaneti, J.1    Kirby, A.J.2    Koedjikov, A.H.3    Pojarlieff, I.G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.