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Volumn 7, Issue 4, 2005, Pages 609-611

Synthesis of trisubstituted imidazoles by palladium-catalyzed cyclization of O-pentafluorobenzoylamidoximes: Application to amino acid mimetics with a C-terminal imidazole

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BENZENE DERIVATIVE; FLUORINE DERIVATIVE; IMIDAZOLE DERIVATIVE; PALLADIUM COMPLEX; TRIETHYLAMINE;

EID: 14844351354     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047628p     Document Type: Article
Times cited : (126)

References (25)
  • 2
    • 1442358592 scopus 로고    scopus 로고
    • Omotowa, B. A.; Shreeve, J. M. Organometallics 2004, 23, 783. Liu, J.; Zhao, Y.; Zhou, Y.; Li, L.; Zhang, T. Y.; Zhang, H. Org. Biomol. Chem. 2003, 1, 3227.
    • (2004) Organometallics , vol.23 , pp. 783
    • Omotowa, B.A.1    Shreeve, J.M.2
  • 4
    • 0002397515 scopus 로고    scopus 로고
    • Katritzky, A. R.; Ress, C. W.; Scriven. E. F. V., Eds.; Pergamon Press: Oxford
    • Grimmett, M. R. In Comprehensive Heterocyclic Chemistry II: Katritzky, A. R.; Ress, C. W.; Scriven. E. F. V., Eds.; Pergamon Press: Oxford, 1996: Vol. 3, pp 77-220.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.3 , pp. 77-220
    • Grimmett, M.R.1
  • 7
    • 0031584889 scopus 로고    scopus 로고
    • Von Geldern, T. W.; Kester, J. A.; Bal, R.: Wu-Wong, J. R.; Chiou, W.; Dixon, D. B.; Opgenorth, T. J. J. Med. Chem. 1996, 39, 968. Predgen, L. N.; Mokhallalati, M. K.; Mcguire, M. A. Tetrahedron Lett. 1997, 38, 1275.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1275
    • Predgen, L.N.1    Mokhallalati, M.K.2    Mcguire, M.A.3
  • 10
    • 0035945749 scopus 로고    scopus 로고
    • Hlasta, D. J. Org. Lett. 2001, 3, 157. Deng, Y.; Hlasta, D. J. Tetrahedron Lett. 2002, 43, 189.
    • (2001) Org. Lett. , vol.3 , pp. 157
    • Hlasta, D.J.1
  • 12
    • 0038322529 scopus 로고    scopus 로고
    • Kitamura, M.; Narasaka, K. Chem. Record 2002, 2, 268. Kitamura, M.; Chiba, S.; Saku, O.; Narasaka, K. Chem. Lett. 2002, 606. Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. Tsutsui, H.; Narasaka, K. Chem. Lett. 2001, 526.
    • (2002) Chem. Record , vol.2 , pp. 268
    • Kitamura, M.1    Narasaka, K.2
  • 13
    • 0036335247 scopus 로고    scopus 로고
    • Kitamura, M.; Narasaka, K. Chem. Record 2002, 2, 268. Kitamura, M.; Chiba, S.; Saku, O.; Narasaka, K. Chem. Lett. 2002, 606. Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. Tsutsui, H.; Narasaka, K. Chem. Lett. 2001, 526.
    • (2002) Chem. Lett. , pp. 606
    • Kitamura, M.1    Chiba, S.2    Saku, O.3    Narasaka, K.4
  • 14
    • 0033472776 scopus 로고    scopus 로고
    • Kitamura, M.; Narasaka, K. Chem. Record 2002, 2, 268. Kitamura, M.; Chiba, S.; Saku, O.; Narasaka, K. Chem. Lett. 2002, 606. Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. Tsutsui, H.; Narasaka, K. Chem. Lett. 2001, 526.
    • (1999) Chem. Lett. , pp. 45
    • Tsutsui, H.1    Narasaka, K.2
  • 15
    • 0035533933 scopus 로고    scopus 로고
    • Kitamura, M.; Narasaka, K. Chem. Record 2002, 2, 268. Kitamura, M.; Chiba, S.; Saku, O.; Narasaka, K. Chem. Lett. 2002, 606. Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45. Tsutsui, H.; Narasaka, K. Chem. Lett. 2001, 526.
    • (2001) Chem. Lett. , pp. 526
    • Tsutsui, H.1    Narasaka, K.2
  • 20
    • 33847798303 scopus 로고
    • It has been noted that O-alkyl hydroxamoyl chlorides isomerize to the thermodynamically stable (E)-isomer and that these react stereospecifically to give an (E)-amidoxime (Johnson, J. E.; Nalley, E. A.; Kunz, Y. K.; Springfield, J. R. J. Org. Chem. 1976, 41, 252. Johnson, J. E.; Todd, S. L.; Dutson, S. M.; Ghafouripour, A.; Alderman, R. M.; Hotema. M. R. J. Org. Chem. 1992, 57, 4648). Note that the substituent priorities of 2 and 3/4 are different such that the respective (E)-isomers have opposite relative configurations.
    • (1976) J. Org. Chem. , vol.41 , pp. 252
    • Johnson, J.E.1    Nalley, E.A.2    Kunz, Y.K.3    Springfield, J.R.4
  • 21
    • 0343227985 scopus 로고
    • It has been noted that O-alkyl hydroxamoyl chlorides isomerize to the thermodynamically stable (E)-isomer and that these react stereospecifically to give an (E)-amidoxime (Johnson, J. E.; Nalley, E. A.; Kunz, Y. K.; Springfield, J. R. J. Org. Chem. 1976, 41, 252. Johnson, J. E.; Todd, S. L.; Dutson, S. M.; Ghafouripour, A.; Alderman, R. M.; Hotema. M. R. J. Org. Chem. 1992, 57, 4648). Note that the substituent priorities of 2 and 3/4 are different such that the respective (E)-isomers have opposite relative configurations.
    • (1992) J. Org. Chem. , vol.57 , pp. 4648
    • Johnson, J.E.1    Todd, S.L.2    Dutson, S.M.3    Ghafouripour, A.4    Alderman, R.M.5    Hotema, M.R.6
  • 25
    • 0022412803 scopus 로고
    • Assignment of isomers is ambiguous and, in any event, unimportant since both react in the subsequent amino Heck reactions. However, the literature suggests that for the amidoximes, the (Z)-isomer would be major (Sauve, G.; Rao, V. S.; Lajoie, G.; Belleau, B. Can. J. Chem. 1985, 63, 3089).
    • (1985) Can. J. Chem. , vol.63 , pp. 3089
    • Sauve, G.1    Rao, V.S.2    Lajoie, G.3    Belleau, B.4


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