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Volumn , Issue 16, 2000, Pages 2915-2921

Silicon-assisted ethoxycarbonylmethylation of N-methylquinolinium and isoquinolinium iodides

Author keywords

Alkylations; ETSA; Nucleophilic additions; Quinolinium salts

Indexed keywords

ACETALDEHYDE; CESIUM; FLUORIDE; HETEROCYCLIC COMPOUND;

EID: 0033849656     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200008)2000:16<2915::AID-EJOC2915>3.0.CO;2-B     Document Type: Article
Times cited : (20)

References (38)
  • 1
    • 6744257232 scopus 로고    scopus 로고
    • U.S. US 5,939,435, 1999, American Home Product Corporation, USA
    • See as example: J. Babiak, H. M. Elokdah, C. P. Miller, T. S. Sulkowski, U.S. US 5,939,435, 1999, American Home Product Corporation, USA.
    • Babiak, J.1    Elokdah, H.M.2    Miller, C.P.3    Sulkowski, T.S.4
  • 5
    • 6744241750 scopus 로고
    • Ed. Paquette, John Wiley & Sons, Inc.: New York, and references therein
    • See as examples: D. J. Ager. In Encyclopaedia of Reagents for Organic Synthesis, Ed. Paquette, John Wiley & Sons, Inc.: New York, 1995, Vol. 4, pp 2523-2525 and references therein.
    • (1995) Encyclopaedia of Reagents for Organic Synthesis , vol.4 , pp. 2523-2525
    • Ager, D.J.1
  • 12
    • 0004064176 scopus 로고
    • Springer Verlag, Berlin
    • -1) is usually a highly exothermic process, which provides the driving force for a number of useful synthetic reactions. For reviews, see as examples: [8a] W. P. Weber in Silicon Reagents for Organic Synthesis, Springer Verlag, Berlin, 1983. [8b] E. W. Colvin, Silicon Organic Synthesis, Butterworths. London, 1981. [8c] G. G. Yakobson, N. E. Akhmetova, Synthesis 1983, 169-184. [8d] J. H. Clark, Chem. Rev. 1980, 80, 429-452.
    • (1983) Silicon Reagents for Organic Synthesis
    • Weber, W.P.1
  • 13
    • 0004095340 scopus 로고
    • Butterworths. London
    • -1) is usually a highly exothermic process, which provides the driving force for a number of useful synthetic reactions. For reviews, see as examples: [8a] W. P. Weber in Silicon Reagents for Organic Synthesis, Springer Verlag, Berlin, 1983. [8b] E. W. Colvin, Silicon Organic Synthesis, Butterworths. London, 1981. [8c] G. G. Yakobson, N. E. Akhmetova, Synthesis 1983, 169-184. [8d] J. H. Clark, Chem. Rev. 1980, 80, 429-452.
    • (1981) Silicon Organic Synthesis
    • Colvin, E.W.1
  • 14
    • 85082935857 scopus 로고
    • -1) is usually a highly exothermic process, which provides the driving force for a number of useful synthetic reactions. For reviews, see as examples: [8a] W. P. Weber in Silicon Reagents for Organic Synthesis, Springer Verlag, Berlin, 1983. [8b] E. W. Colvin, Silicon Organic Synthesis, Butterworths. London, 1981. [8c] G. G. Yakobson, N. E. Akhmetova, Synthesis 1983, 169-184. [8d] J. H. Clark, Chem. Rev. 1980, 80, 429-452.
    • (1983) Synthesis , pp. 169-184
    • Yakobson, G.G.1    Akhmetova, N.E.2
  • 15
    • 33847086648 scopus 로고
    • -1) is usually a highly exothermic process, which provides the driving force for a number of useful synthetic reactions. For reviews, see as examples: [8a] W. P. Weber in Silicon Reagents for Organic Synthesis, Springer Verlag, Berlin, 1983. [8b] E. W. Colvin, Silicon Organic Synthesis, Butterworths. London, 1981. [8c] G. G. Yakobson, N. E. Akhmetova, Synthesis 1983, 169-184. [8d] J. H. Clark, Chem. Rev. 1980, 80, 429-452.
    • (1980) Chem. Rev. , vol.80 , pp. 429-452
    • Clark, J.H.1
  • 16
    • 0000338523 scopus 로고
    • and references therein
    • The larger dielectric constant of acetonitrile (ε = 35.94) allows for the formation of a solvent-separated ion pair, while THF (ε = 7.58) or dichloromethane (ε = 8.93) should hinder the dissociation. A. Loupy, B. Tchoubar, D. Astruc, Chem. Rev. 1992, 1141-1165 and references therein.
    • (1992) Chem. Rev. , pp. 1141-1165
    • Loupy, A.1    Tchoubar, B.2    Astruc, D.3
  • 19
    • 6744265009 scopus 로고
    • Melting point as well as spectroscopic data are identical to literature: La Coste, W. Ber. 1882, 15, 186. M. Grignon-Dubois, A. Meola, Synth. Commun. 1995, 25 (19), 2999-3006.
    • (1882) Ber. , vol.15 , pp. 186
    • La Coste, W.1
  • 20
    • 0029166416 scopus 로고
    • Melting point as well as spectroscopic data are identical to literature: La Coste, W. Ber. 1882, 15, 186. M. Grignon-Dubois, A. Meola, Synth. Commun. 1995, 25 (19), 2999-3006.
    • (1995) Synth. Commun. , vol.25 , Issue.19 , pp. 2999-3006
    • Grignon-Dubois, M.1    Meola, A.2
  • 21
    • 6744251722 scopus 로고    scopus 로고
    • note
    • -1), using an RHF Hamiltonian. In the case of the C-2 adducts, the AM1 method was also used.
  • 22
    • 6744267781 scopus 로고    scopus 로고
    • note
    • [12b] These kinds of derivatives appear to be unknown in the literature.
  • 29
    • 0343335220 scopus 로고
    • Wiley, New York
    • For reviews, see: [16a] N. Y. Sidgewick, F. R. S. Sidgewick, The Organic Chemistry of Nitrogen; Clarendon Press, Oxford, 1966, p 718. [16b] J. Gurnos, Quinolines, Wiley, New York, 1982.
    • (1982) Quinolines
    • Gurnos, J.1
  • 30
    • 0342900146 scopus 로고
    • See, for example: [17a] J. Metzger, H. Larivé, E.-J. Vincent, R. Dennilauler, R. Baralle, C. Gaurat, Bull. Soc. Chim. Fr. 1967, 30-40. [17b] G. T. Pilyugin, B. M. Gutsulyak, Usp. Khim. 1963, 32 (4), 389-432 (Chem. Abstr. 1963, 59, 3889b). [17c] J. W. Bunting, W. G. Meathrel, Tetrahedron Lett. 1971, 133-136. [17d] S. Fukuzumi, S. Noura, J. Chem. Soc., Chem. Commun. 1994, 287-288. [17e] M. Maeda, Chem. Pharm. Bull. 1990, 38, 2577-2580.
    • (1967) Bull. Soc. Chim. Fr. , pp. 30-40
    • Metzger, J.1    Larivé, H.2    Vincent, E.-J.3    Dennilauler, R.4    Baralle, R.5    Gaurat, C.6
  • 31
    • 0001483375 scopus 로고
    • See, for example: [17a] J. Metzger, H. Larivé, E.-J. Vincent, R. Dennilauler, R. Baralle, C. Gaurat, Bull. Soc. Chim. Fr. 1967, 30-40. [17b] G. T. Pilyugin, B. M. Gutsulyak, Usp. Khim. 1963, 32 (4), 389-432 (Chem. Abstr. 1963, 59, 3889b). [17c] J. W. Bunting, W. G. Meathrel, Tetrahedron Lett. 1971, 133-136. [17d] S. Fukuzumi, S. Noura, J. Chem. Soc., Chem. Commun. 1994, 287-288. [17e] M. Maeda, Chem. Pharm. Bull. 1990, 38, 2577-2580.
    • (1963) Usp. Khim. , vol.32 , Issue.4 , pp. 389-432
    • Pilyugin, G.T.1    Gutsulyak, B.M.2
  • 32
    • 6744220929 scopus 로고
    • See, for example: [17a] J. Metzger, H. Larivé, E.-J. Vincent, R. Dennilauler, R. Baralle, C. Gaurat, Bull. Soc. Chim. Fr. 1967, 30-40. [17b] G. T. Pilyugin, B. M. Gutsulyak, Usp. Khim. 1963, 32 (4), 389-432 (Chem. Abstr. 1963, 59, 3889b). [17c] J. W. Bunting, W. G. Meathrel, Tetrahedron Lett. 1971, 133-136. [17d] S. Fukuzumi, S. Noura, J. Chem. Soc., Chem. Commun. 1994, 287-288. [17e] M. Maeda, Chem. Pharm. Bull. 1990, 38, 2577-2580.
    • (1963) Chem. Abstr. , vol.59
  • 33
    • 0011998461 scopus 로고
    • See, for example: [17a] J. Metzger, H. Larivé, E.-J. Vincent, R. Dennilauler, R. Baralle, C. Gaurat, Bull. Soc. Chim. Fr. 1967, 30-40. [17b] G. T. Pilyugin, B. M. Gutsulyak, Usp. Khim. 1963, 32 (4), 389-432 (Chem. Abstr. 1963, 59, 3889b). [17c] J. W. Bunting, W. G. Meathrel, Tetrahedron Lett. 1971, 133-136. [17d] S. Fukuzumi, S. Noura, J. Chem. Soc., Chem. Commun. 1994, 287-288. [17e] M. Maeda, Chem. Pharm. Bull. 1990, 38, 2577-2580.
    • (1971) Tetrahedron Lett. , pp. 133-136
    • Bunting, J.W.1    Meathrel, W.G.2
  • 34
    • 37049072085 scopus 로고
    • See, for example: [17a] J. Metzger, H. Larivé, E.-J. Vincent, R. Dennilauler, R. Baralle, C. Gaurat, Bull. Soc. Chim. Fr. 1967, 30-40. [17b] G. T. Pilyugin, B. M. Gutsulyak, Usp. Khim. 1963, 32 (4), 389-432 (Chem. Abstr. 1963, 59, 3889b). [17c] J. W. Bunting, W. G. Meathrel, Tetrahedron Lett. 1971, 133-136. [17d] S. Fukuzumi, S. Noura, J. Chem. Soc., Chem. Commun. 1994, 287-288. [17e] M. Maeda, Chem. Pharm. Bull. 1990, 38, 2577-2580.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 287-288
    • Fukuzumi, S.1    Noura, S.2
  • 35
    • 0025184299 scopus 로고
    • See, for example: [17a] J. Metzger, H. Larivé, E.-J. Vincent, R. Dennilauler, R. Baralle, C. Gaurat, Bull. Soc. Chim. Fr. 1967, 30-40. [17b] G. T. Pilyugin, B. M. Gutsulyak, Usp. Khim. 1963, 32 (4), 389-432 (Chem. Abstr. 1963, 59, 3889b). [17c] J. W. Bunting, W. G. Meathrel, Tetrahedron Lett. 1971, 133-136. [17d] S. Fukuzumi, S. Noura, J. Chem. Soc., Chem. Commun. 1994, 287-288. [17e] M. Maeda, Chem. Pharm. Bull. 1990, 38, 2577-2580.
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 2577-2580
    • Maeda, M.1
  • 36
    • 6744257230 scopus 로고    scopus 로고
    • note
    • Heats of formation for the pair of regioisomers were calculated on a 486 PC-compatible running the programs PCMODEL, version 4.1 and GMMX, version 1.0 (from Serena Software, P.O. Box 3076, Bloomington, IN 47402-3076). Both use the features of Allinger's MMX force-field, including pi-valence electron self consistent field calculations.


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