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Volumn 35, Issue 9, 2005, Pages 1239-1251

Synthesis of α-substituted N-aryl acrylamide derivatives through Baylis-Hillman reaction

Author keywords

Aromatic aldehyde; Baylis Hillman reaction; N aryl acrylamide

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; ACRYLAMIDE DERIVATIVE; ALDEHYDE DERIVATIVE; N (2 PYRIDYL) 3 HYDROXY 2 METHYLENE 3(2 NITROPHENYL)PROPIONAMIDE; N (2 PYRIDYL) 3 HYDROXY 2 METHYLENE 3(2 PYRIDYL)PROPIONAMIDE; N (2 PYRIDYL) 3 HYDROXY 2 METHYLENE 3(3 NITROPHENYL)PROPIONAMIDE; N (2 PYRIDYL) 3 HYDROXY 2 METHYLENE 3(3 PYRIDYL)PROPIONAMIDE; N (2 PYRIDYL) 3 HYDROXY 2 METHYLENE 3(4 NITROPHENYL)PROPIONAMIDE; N (2 PYRIDYL) 3 HYDROXY 2 METHYLENE 3(4 PYRIDYL)PROPIONAMIDE; N (4 CHLOROPHENYL) 3 HYDROXY 2 METHYLENE 3(3 NITROPHENYL)PROPIONAMIDE; N (4 CHLOROPHENYL) 3 HYDROXY 2 METHYLENE 3(PYRIDIN 2 YL)PROPIONAMIDE; N (4 CHLOROPHENYL) 3 HYDROXY 2 METHYLENE 3(PYRIDIN 3 YL)PROPIONAMIDE; N (4 CHLOROPHENYL) 3 HYDROXY 2 METHYLENE 3(PYRIDIN 4 YL)PROPIONAMIDE; N (4 METHOXYPHENYL) 3 HYDROXY 2 METHYLENE 3(3 NITROPHENYL)PROPIONAMIDE; N (4 METHYLPHENYL) 3 HYDROXY 2 METHYLENE 3(2 NITROPHENYL)PROPIONAMIDE; N (4 METHYLPHENYL) 3 HYDROXY 2 METHYLENE 3(3 NITROPHENYL)PROPIONAMIDE; N (4 NITROPHENYL) 3 HYDROXY 2 METHYLENE 3(2 NITROPHENYL)PROPIONAMIDE; N (4 NITROPHENYL) 3 HYDROXY 2 METHYLENE 3(3 NITROPHENYL)PROPIONAMIDE; N (4 NITROPHENYL) 3 HYDROXY 2 METHYLENE 3(PYRIDIN 2 YL)PROPIONAMIDE; N (4 NITROPHENYL) 3 HYDROXY 2 METHYLENE 3(PYRIDIN 3 YL)PROPIONAMIDE; N (4 NITROPHENYL) 3 HYDROXY 2 METHYLENE 3(PYRIDIN 4 YL)PROPIONAMIDE; N ALKYL ACRYLAMIDE; N ALPHA NAPTHYL 3 HYDROXY 2 METHYLENE 3(3 NITROPHENYL)PROPIONAMIDE; N ARYL ACRYLAMIDE; N BETA NAPTHYL 3 HYDROXY 2 METHYLENE 3(3 NITROPHENYL)PROPIONAMIDE; PROPIONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 18744414203     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200054850     Document Type: Article
Times cited : (23)

References (23)
  • 1
    • 0037366617 scopus 로고    scopus 로고
    • Recent advances in the Baylis-Hillman reaction and applications
    • Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Recent advances in the Baylis-Hillman reaction and applications. Chem. Rev. 2003, 103, 811.
    • (2003) Chem. Rev. , vol.103 , pp. 811
    • Basavaiah, D.1    Rao, A.J.2    Satyanarayana, T.3
  • 2
    • 0000737917 scopus 로고
    • Functionalisation of the α-position of acrylate systems by the addition of carbonyl compounds: Highly pressure-dependent reactions
    • Hill, J. S.; Isaacs, N. S. Functionalisation of the α-position of acrylate systems by the addition of carbonyl compounds: Highly pressure-dependent reactions. Tetrahedron Lett. 1986, 27, 5007.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 5007
    • Hill, J.S.1    Isaacs, N.S.2
  • 3
    • 84980400317 scopus 로고
    • Microwave mediated extensive rate enhancement of the Baylis-Hillman reaction
    • Kundu, M. K.; Mukherjee, S. B.; Balu, N.; Padmakumar, R.; Bhat, S. V. Microwave mediated extensive rate enhancement of the Baylis-Hillman reaction. Synlett 1994, 6, 444.
    • (1994) Synlett , vol.6 , pp. 444
    • Kundu, M.K.1    Mukherjee, S.B.2    Balu, N.3    Padmakumar, R.4    Bhat, S.V.5
  • 4
    • 0037432359 scopus 로고    scopus 로고
    • Conditions for facile, controlled RAFT polymerization of acrylamide in water
    • Thomas, D. B.; Sumerlin, B. S.; Lowe, A. B.; McCormick, C. L. Conditions for facile, controlled RAFT polymerization of acrylamide in water. Macromolecules 2003, 36, 1436.
    • (2003) Macromolecules , vol.36 , pp. 1436
    • Thomas, D.B.1    Sumerlin, B.S.2    Lowe, A.B.3    McCormick, C.L.4
  • 5
    • 0034827510 scopus 로고    scopus 로고
    • Efficient Lewis acid-catalyzed stereocontrolled radical polymerization of acrylamides
    • Isobe, Y.; Fujioka, D.; Habaue, S.; Okamoto, Y. Efficient Lewis acid-catalyzed stereocontrolled radical polymerization of acrylamides. J. Am. Chem. Soc. 2001, 123, 7180.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7180
    • Isobe, Y.1    Fujioka, D.2    Habaue, S.3    Okamoto, Y.4
  • 6
    • 0037042302 scopus 로고    scopus 로고
    • Hydrogen bonding and the conformations of poly(alkyl acrylamides)
    • Duffy, D. M.; Rodger, P. M. Hydrogen bonding and the conformations of poly(alkyl acrylamides). J. Am. Chem. Soc. 2002, 124, 5206.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 5206
    • Duffy, D.M.1    Rodger, P.M.2
  • 7
    • 0042921620 scopus 로고    scopus 로고
    • Fluorine substitution can block CYP3A4 metabolism-dependent inhibition: Identification of (S)-N-[1-(4-fluoro-3-morpholin-4-yl phenyl)ethyl]-3-(4- fluorophenyl)acrylamide as an orally bioavailable KCNQ2 opener devoid of CYP3A4 metabolism-dependent inhibition
    • Wu, Y.; Davis, C. D.; Dworetzky, S.; Fitzpatrick, W. C.; Harden, D.; He, H.; Knox, R. J.; Newton, A. E.; Philip, T.; Polson, C.; Sivarao, D. V.; Sun, L.; Tertyshnikova, S.; Weaver, D.; Yeola, S.; Zoeckler, M.; Sinz, M. W. Fluorine substitution can block CYP3A4 metabolism-dependent inhibition: Identification of (S)-N-[1-(4-fluoro-3-morpholin-4-yl phenyl)ethyl]-3-(4-fluorophenyl)acrylamide as an orally bioavailable KCNQ2 opener devoid of CYP3A4 metabolism-dependent inhibition. J. Med. Chem. 2003, 46, 3778.
    • (2003) J. Med. Chem. , vol.46 , pp. 3778
    • Wu, Y.1    Davis, C.D.2    Dworetzky, S.3    Fitzpatrick, W.C.4    Harden, D.5    He, H.6    Knox, R.J.7    Newton, A.E.8    Philip, T.9    Polson, C.10    Sivarao, D.V.11    Sun, L.12    Tertyshnikova, S.13    Weaver, D.14    Yeola, S.15    Zoeckler, M.16    Sinz, M.W.17
  • 8
    • 0344550397 scopus 로고    scopus 로고
    • A method for designing conformationally restricted analogues based on allylic strain: Synthesis of a novel class of noncompetitive NMDA receptor antagonists having the acrylamide structure
    • Ohmori, Y.; Yamashita, A.; Tsujita, R.; Yamamoto, T.; Taniuchi, K.; Matsuda, A.; Shuto, S. A method for designing conformationally restricted analogues based on allylic strain: Synthesis of a novel class of noncompetitive NMDA receptor antagonists having the acrylamide structure. J. Med. Chem. 2003, 46, 5326.
    • (2003) J. Med. Chem. , vol.46 , pp. 5326
    • Ohmori, Y.1    Yamashita, A.2    Tsujita, R.3    Yamamoto, T.4    Taniuchi, K.5    Matsuda, A.6    Shuto, S.7
  • 10
    • 0000892247 scopus 로고    scopus 로고
    • The catalyzed α-hydroxyalkylation and α-aminoalkylation of activated olefins (the Morita-Baylis-Hillman reaction)
    • Ciganek, E. The catalyzed α-hydroxyalkylation and α-aminoalkylation of activated olefins (the Morita-Baylis-Hillman reaction). Org. React. 1997, 51, 201.
    • (1997) Org. React. , vol.51 , pp. 201
    • Ciganek, E.1
  • 11
    • 0037059441 scopus 로고    scopus 로고
    • Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes
    • Yu, C.; Hu, L. Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes. J. Org. Chem. 2002, 67, 219.
    • (2002) J. Org. Chem. , vol.67 , pp. 219
    • Yu, C.1    Hu, L.2
  • 12
    • 4644231912 scopus 로고    scopus 로고
    • Acrylamide in the Baylis-Hillman reaction: Expanded reaction scope and the unexpected superiority of DABCO over more basic tertiary amine catalysts
    • Faltin, C.; Fleming, E. M.; Connon, S. J. Acrylamide in the Baylis-Hillman reaction: Expanded reaction scope and the unexpected superiority of DABCO over more basic tertiary amine catalysts. J. Org. Chem. 2004, 69, 6496.
    • (2004) J. Org. Chem. , vol.69 , pp. 6496
    • Faltin, C.1    Fleming, E.M.2    Connon, S.J.3
  • 13
    • 0035823312 scopus 로고    scopus 로고
    • A remarkable rate acceleration of the Baylis-Hillman reaction
    • Lee, W.; Yang, K.; Chen, K. A remarkable rate acceleration of the Baylis-Hillman reaction. Chem. Commun. 2001, 1612.
    • (2001) Chem. Commun. , pp. 1612
    • Lee, W.1    Yang, K.2    Chen, K.3
  • 15
    • 0035822774 scopus 로고    scopus 로고
    • The formyl C-H⋯O hydrogen bond as a critical factor in enantioselective Lewis acid-catalyzed reactions of aldehydes
    • Corey, E. J.; Lee, T. W. The formyl C-H⋯O hydrogen bond as a critical factor in enantioselective Lewis acid-catalyzed reactions of aldehydes. Chem. Commun. 2001, 1321.
    • (2001) Chem. Commun. , pp. 1321
    • Corey, E.J.1    Lee, T.W.2
  • 16
    • 0034622107 scopus 로고    scopus 로고
    • Effect of C=O⋯H-Ar interaction on endo/exo selectivity in the Diels-Alder reaction of phenyl-substituted cyclopentadienones
    • Yoshitake, Y.; Nakagawa, H.; Eto, M.; Harano, K. Effect of C=O⋯H-Ar interaction on endo/exo selectivity in the Diels-Alder reaction of phenyl-substituted cyclopentadienones. Tetrahedron Lett. 2000, 41, 4395.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4395
    • Yoshitake, Y.1    Nakagawa, H.2    Eto, M.3    Harano, K.4
  • 19
    • 0141563670 scopus 로고    scopus 로고
    • Attachment of unreactive amines to the solid support: Synthesis of phenyl-substituted anilines, 2-aminopyridines, and 2-aminopyrimidines
    • Zhu, S.; Shi, S.; Gerritz, S. W.; Sofia, M. J. Attachment of unreactive amines to the solid support: Synthesis of phenyl-substituted anilines, 2-aminopyridines, and 2-aminopyrimidines. J. Comb. Chem. 2003, 5, 205.
    • (2003) J. Comb. Chem. , vol.5 , pp. 205
    • Zhu, S.1    Shi, S.2    Gerritz, S.W.3    Sofia, M.J.4
  • 20
    • 0037026456 scopus 로고    scopus 로고
    • A mild method for the formation and in situ reaction of imidoyl chlorides: Conversion of pyridine-1-oxides to 2-aminopyridine amides
    • Manley, P. J.; Bilodeau, M. T. A mild method for the formation and in situ reaction of imidoyl chlorides: Conversion of pyridine-1-oxides to 2-aminopyridine amides. Org. Lett. 2002, 4, 3127.
    • (2002) Org. Lett. , vol.4 , pp. 3127
    • Manley, P.J.1    Bilodeau, M.T.2
  • 21
    • 0001111464 scopus 로고    scopus 로고
    • N-Azinylpyridinium N-aminides: Intermediates for the regioselective synthesis of 3-fluoro-2-aminopyridine derivatives
    • Viedma, A. G.; Martinez-Barrasa, V.; Burgos, C.; Izquierdo, M. L.; Alvarez-Builla, J. N-Azinylpyridinium N-aminides: Intermediates for the regioselective synthesis of 3-fluoro-2-aminopyridine derivatives. J. Org. Chem. 1999, 64, 1007.
    • (1999) J. Org. Chem. , vol.64 , pp. 1007
    • Viedma, A.G.1    Martinez-Barrasa, V.2    Burgos, C.3    Izquierdo, M.L.4    Alvarez-Builla, J.5
  • 22
    • 0030844722 scopus 로고    scopus 로고
    • 5-Substituted 2-aminopyridine C-nucleosides as protonated cytidine equivalents: Increasing efficiency and selectivity in DNA triple-helix formation
    • Hildbrand, S.; Blaser, A.; Parel, S. P.; Leumann, C. J. 5-Substituted 2-aminopyridine C-nucleosides as protonated cytidine equivalents: increasing efficiency and selectivity in DNA triple-helix formation. J. Am. Soc. Chem. 1997, 119, 5499.
    • (1997) J. Am. Soc. Chem. , vol.119 , pp. 5499
    • Hildbrand, S.1    Blaser, A.2    Parel, S.P.3    Leumann, C.J.4
  • 23
    • 0005786141 scopus 로고
    • Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles
    • Vijn, R. J.; Arts, H. J.; Mass, P. J.; Castelijns, A. M. Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles. J. Org. Chem. 1993, 58, 887.
    • (1993) J. Org. Chem. , vol.58 , pp. 887
    • Vijn, R.J.1    Arts, H.J.2    Mass, P.J.3    Castelijns, A.M.4


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