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

โœ Scribed by Carlo Dell'Erba; Marino Novi; Giovanni Petrillo; Cinzia Tavani


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
766 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis


Tile reactions of atylazosulfones 1 (ArN=NSO2Ar ') with tile potassium sails of (tertbutox'ycarbonyl)methyl 2 and losyllnethyl isocyanide 3 in DMSO afford 4.5-bis(tert-butoxycarbonyl)-4 and 4-tosyl-l-arylimidazoles 5, respectively. Yields of imidazoles 4 and 5 vary from moderate to excellent depending on the nature both of Ar in 1 and of the nucleophile (2 or 3) employed A comparison of the results obtained with those relevant to the reactions of the same uucleophiles with nitrosobenzene in aualogous experimental conditions provides usefid mechalustic indications on the transformation of I 1o 4 or 5.


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