. -The direct iodination of a representative range of aromatic amines and phenols is performed both under solution-phase and solvent-free conditions by grinding the reactants in a mortar with a pestle. The solvent-free oxyiodination with a combination of KI and tBu-O-OH is a mild method for the regioselective introduction of an iodo substituent in activated and deactivated aromatic compounds under neutral conditions. The solvent-free protocol affords satisfactory yields of the generally obtained monoiodinated products. -(VENKATESHWARLU, G.; PREMALATHA, A.; CHAKRADHAR, A.; RAJANNA, K. C.; PRAKASH*, P. K. S.; Helv. Chim. Acta 93 (2010) 2, 345-349; Dep. Chem., Osmania Univ., Hyderabad 500 007, India; Eng.) -H. Hoennerscheid 26-042
Iodination of certain aromatic amines and phenols are triggered by the oxidation of KI by peroxy compounds such as tert‐butyl hydroperoxide (tBuOOH) under liquid‐phase and solvent‐free conditions by grinding the reactants in a mortar with a pestle. The reactions afforded corresponding iodo derivatives in good yield with high regioselectivity (Table 1).
In this investigation 4-(benzo[d]thiazol-2-yl)benzenamine was reacted with aryl isothiocyanates to give 1-(4-(benzo[d]thiazol-2-yl)phenyl)-3-aryl thioureas 2, which were cyclized with acid to afford 3-(4-(benzo[d]thiazol-2-yl)phenyl)-5-aryl-1,3,5-oxadiazinane-4-thiones 3. On the other hand, 1-(4-(benzo[d]thiazol-2-yl)phenyl)-5-methyl-3-aryl-1,3,5-triazinane-2-thiones 4 were obtained when compounds 2 were treated with amines.
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