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Volumn 53, Issue 20, 1997, Pages 6937-6958

Ambident heterocyclic reactivity: Intramolecular alkylations of 2,4-disubstituted benzimidazoles

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE DERIVATIVE;

EID: 0030929363     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00394-3     Document Type: Article
Times cited : (13)

References (49)
  • 4
    • 0342830707 scopus 로고    scopus 로고
    • note
    • The standard nomenclature of tautomeric 4(7)-substituted benzimidazoles (and their related N-alkyl) systems, as exemplified by 4-methyl-1H-benzimidazole ⇆ 7-methyl-1H-benzimidazole is awkward to use when describing competitive nitrogen alkylation reactions. Rather than using the pyrrolic nitrogen (>N-R) as the numeric origin, we give the benzenoid ring substituent a fixed (lower) number and use this to assign the N1 and N3 sites (see Fig. 1); this leads to a more convenient description of the isomeric products.
  • 14
    • 0342830699 scopus 로고    scopus 로고
    • note
    • The selectivity factor is the differential free energy for reaction at the competitive N1-and N3-sites of the benzimidazole anion under consideration, s = ΔΔG‡ = -RT ln(N1% / N3%) kJ/mol.
  • 19
    • 0344361923 scopus 로고
    • Baldwin, J.E. J.C.S., Chem. Commun. 1976, 734-736. The Baldwin cyclization rules are inherently based on conformational access to transition state geometries incorporating preferred approach vectors for SN2 substitutions and addition reactions to multiple bonds.
    • (1976) J.C.S., Chem. Commun. , pp. 734-736
    • Baldwin, J.E.1
  • 28
    • 0343265567 scopus 로고
    • See DeSelms, R.C. J. Org. Chem. 1962, 27, 2165-2167, for a related synthetic route to 2-(ω-bromoalkyl)benzimidazoles and their base induced cyclizations to tricyclic fused ring systems.
    • (1962) J. Org. Chem. , vol.27 , pp. 2165-2167
    • DeSelms, R.C.1
  • 30
    • 0342830685 scopus 로고
    • Preston, P.N. Ed.; Interscience: New York, Pt II, Chpt. 6,7
    • Tennant, G. in Chemistry of Heterocyclic Compounds, Preston, P.N. Ed.; Interscience: New York, Vol. 40, Pt II, 1980, Chpt. 6,7.
    • (1980) Chemistry of Heterocyclic Compounds , vol.40 , Issue.PART II
    • Tennant, G.1
  • 32
    • 0342395896 scopus 로고    scopus 로고
    • Polygen Corp., 200 Fifth Ave, Waltham, MA 02154 USA
    • a) Polygen Corp., 200 Fifth Ave, Waltham, MA 02154 USA.
  • 40
    • 33847086890 scopus 로고    scopus 로고
    • c) Arnett, E.M.; Reich, R. J. Am. Chem. Soc. 1980, 102, 5892-5902, but see Kevill, D.N. J.C.S., Chem. Comm. 1981, 421-422 for a critical reappraisal.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5892-5902
    • Arnett, E.M.1    Reich, R.2
  • 41
    • 33847086890 scopus 로고    scopus 로고
    • c) Arnett, E.M.; Reich, R. J. Am. Chem. Soc. 1980, 102, 5892-5902, but see Kevill, D.N. J.C.S., Chem. Comm. 1981, 421-422 for a critical reappraisal.
    • J.C.S., Chem. Comm. , vol.1981 , pp. 421-422
    • Kevill, D.N.1
  • 46
    • 0004105856 scopus 로고
    • Longman Scientific & Technical: UK
    • b) Isaacs, N.S. Physical Organic Chemistry, Longman Scientific & Technical: UK, 1987; pp. 608-613.
    • (1987) Physical Organic Chemistry , pp. 608-613
    • Isaacs, N.S.1
  • 48
    • 0003480898 scopus 로고
    • Baldwin, J.E., Ed.; Pergamon Press: Oxford
    • Derome, A.E. Modern NMR Techniques for Chemistry Research, Baldwin, J.E., Ed.; Pergamon Press: Oxford, Vol. 6, 1987; p. 168. Rabenstein, D.L.;Keire, D.A. in Practical Spectroscopy Series, Vol. II : Modern NMR Techniques and Their Application to Chemistry, Popov, A.I.; Hallinga, K. Eds; Marcel Dekker: New York, 1991; Chpt. 5.
    • (1987) Modern NMR Techniques for Chemistry Research , vol.6 , pp. 168
    • Derome, A.E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.