C. Dell'erba, M. Novi, G. Petrillo
Feb 10, 1997
Citations
0
Influential Citations
12
Citations
Journal
Tetrahedron
Abstract
Abstract The reactions of arylazosulfones 1 (ArNNSO2Ar1) with the potassium salts of (tert-butoxycarbonyl)methyl 2 and tosylmethyl isocyanide 3 in DMSO afford 4,5-bis(tert-butoxycarbonyl)- 4 and 4-tosyl-1-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 nucleophiles with nitrosobenzene in analogous experimental conditions provides useful mechanistic indications on the transformation of 1 to 4 or 5.