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Volumn 34, Issue 3, 1997, Pages 709-716

Nucleophilic Addition to Substituted 1H-4,5-Dihydroimidazolium Salts

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EID: 0001150531     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340302     Document Type: Article
Times cited : (32)

References (42)
  • 2
    • 0004155147 scopus 로고
    • John Wiley and Sons, New York
    • R. L. Blakey and S. J. Benkovic, eds. Folates and Pteridines, Vol 1, Wiley, New York, 1984; Vol 2, John Wiley and Sons, New York, 1985.
    • (1985) Folates and Pteridines , vol.2
  • 3
    • 1542761125 scopus 로고
    • E. Haslam, ed. Chapter 24.3, Pergamon, Oxford
    • H. C. S. Wood, Comprehensive Organic Chemistry, Vol 5, E. Haslam, ed. Chapter 24.3, Pergamon, Oxford, 1979.
    • (1979) Comprehensive Organic Chemistry , vol.5
    • Wood, H.C.S.1
  • 23
    • 1542446301 scopus 로고    scopus 로고
    • note
    • Classically D. Beke considers for analogous compounds that the ionic and covalent structures make up a tautomeric equilibrium, more specifically a case of anionotropy [23].
  • 25
    • 1542446298 scopus 로고    scopus 로고
    • note
    • -1). This is not exceptional as it has been demonstrated that such signal intensity decreases markedly, even failing to appear in certain cases, when there is low electron density in the carbon to which the group is bonded [25].
  • 27
    • 1542761121 scopus 로고    scopus 로고
    • note
    • In contrast, compounds 1a-d undergo thermal decomposition prior to electron impact which originates the corresponding 1H-4,5-dihydroimidazoles and methyl iodide [27].
  • 29
    • 1542655960 scopus 로고    scopus 로고
    • note
    • In the hydrolysis of 5b that leads to N-benzoyl-N-methyl-N'-pheoylethylenediamine (6b) as the final product, two compounds of low Rf were detected, presumably the N-benzoyl-N'-methyl-N-phenyletheyl- enediamine and the intermediate carbinolamine A (Nu=OH) detected in the hydrolysis of 1b [17].
  • 30
    • 1542655962 scopus 로고    scopus 로고
    • note
    • The behavior of compounds 5 with these reagents is similar to that of α-aminonitriles derived from ternary iminium salts [30] that lead mainly to substitution products, as there are no reduction products of the cyano group following treatment with lithium aluminum hydride. Neither are there any addition or other alternative reacting modes when treated with Grignard reagents.
  • 32
    • 1542446303 scopus 로고    scopus 로고
    • note
    • Data concerning these triamino derivatives indicate that as a rule they are unstable [11], unless substituted by three electron-acceptor groups [32,33]. On the other hand, recalling the reported behavior in acid medium of orthoamides obtained from formamidinium salts [34-36], it would be expected that such treatment should regenerate the dihydroimidazolium salt However, the obtained product remains unchanged after treatment with hydrochloric acid solution.
  • 38
    • 1542446304 scopus 로고    scopus 로고
    • note
    • Preliminary unpublished kinetic studies related to the migration of acyl groups in alkaline medium in N-acyl-N-aryl-N'-methyl-alkylenediamines indicate that the rate of rearrangement increases on raising the difference in pKa of the involved nitrogen atoms.
  • 40
    • 1542550923 scopus 로고    scopus 로고
    • note
    • 1,2-Diaryl-1H-4,5-dihydroimidazoles used as reference compounds were the synthetic precursors of compounds 1. The N-aryl-N'-methylethylenediamines 3 were synthesized from N-(2-bromoethyl)-methylamine and the corresponding arylamine [40].


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