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Volumn 53, Issue 6, 1997, Pages 2125-2136

Reactions of arylazosulfones with the conjugate bases of (tert-butoxycarbonyl)methyl and tosylmethyl isocyanide. Synthesis of substituted 1-arylimidazoles

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; ISONITRILE DERIVATIVE; SULFONE DERIVATIVE;

EID: 0031562111     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01108-8     Document Type: Article
Times cited : (14)

References (44)
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    • (1987) , vol.43 , pp. 4625
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    • (1983) rn1 Mechanism
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    • (1993) Tetrahedron , vol.49 , pp. 235
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    • 3 Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1992, 48, 325; Tetrahedron 1993, 49, 235; Tetrahedron 1994, 50, 11239.
    • (1994) Tetrahedron , vol.50 , pp. 11239
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    • Katritzky, A. R.; Rees, C. W.; Potts, K. T.; Eds., Pergamon Press: Oxford
    • 8 a) Grimmett, M. R. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W.; Potts, K. T.; Eds., Pergamon Press: Oxford, 1984; vol. 5, p. 435.
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    • Grimmett, M.R.1
  • 23
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    • Katritzky, A. R.; Rees, C. W.; Potts, K. T.; Eds., Pergamon Press: Oxford
    • 11 For general reviews upon imidazole synthesis and reactivity see: Grimmett, M. R. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W.; Potts, K. T.; Eds., Pergamon Press: Oxford, 1984; vol. 5, p. 457. Grimmett, M. R. in Adv. Heterocycl. Chem. 1980, 27, 241.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.5 , pp. 457
    • Grimmett, M.R.1
  • 24
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    • 11 For general reviews upon imidazole synthesis and reactivity see: Grimmett, M. R. in Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W.; Potts, K. T.; Eds., Pergamon Press: Oxford, 1984; vol. 5, p. 457. Grimmett, M. R. in Adv. Heterocycl. Chem. 1980, 27, 241.
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  • 25
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    • note
    • 12 Traces of p-toluenesulfonamide were found when the process leading to imidazole 5 was less efficient (entries 18, 25, 27).
  • 26
    • 0011390302 scopus 로고    scopus 로고
    • note
    • 13 Experiments in DMSO were also carried out but, after aqueous quenching of the reaction and extraction with ether (see experimental), the evaporation to dryness of the aqueous/DMSO phase presented some practical difficulties. DMF was thus preferred as reaction solvent because of an easier work-up of the aqueous/DMF phase.
  • 28
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    • note
    • 15 No attempt either to identify or to quantify cyanide anion was done.
  • 30
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    • 17 Hoppe, D. Angew. Chem., Int. Ed. Engl. 1974, 13, 789. Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1977, 16, 339. Van Leusen, A. M.; Schaart, F. J.; van Leusen, D. Recl. Trav. Chim. Pays-Bas 1979, 98, 258.
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  • 32
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    • 17 Hoppe, D. Angew. Chem., Int. Ed. Engl. 1974, 13, 789. Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1977, 16, 339. Van Leusen, A. M.; Schaart, F. J.; van Leusen, D. Recl. Trav. Chim. Pays-Bas 1979, 98, 258.
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    • note
    • 1H-NMR absorptions tentatively assigned to 4,5-imidazoline ring protons: δ 7.59 (1H, d, J 1.9 Hz, H-2), 4.87 (1H, d, J 6.9 Hz, H-5) and 4.74 (1H, dd, J 1.9 and 6.9 Hz, H-4).
  • 38
    • 0011443244 scopus 로고    scopus 로고
    • note
    • 21b but physical and spectroscopic data are not reported.


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