Reactions of Aminophenols

A range of reactions at the hydroxyl group, the amino group or through substitution in the ring are shown by aminophenols. Some of these transformations are described in this section. 

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Double oxidation reactions of aminophenols (127) to the corresponding quinone-imines (128) using PIDA and PIFA were utilized for total synthesis of an enediyne antibiotic, ( )-dynemicin A (6), by Danishefsky and co-workers... 

Figure 13. (a) Formation of mixed SAM on Au electrode, (b) immobilization of Fc-D, (c) immobilization of thiolated capture probe with bifunctional linker (succinimidyl 4-(/V-maleimidomethyl)cyclohexane-l-carboxylate (SMCC)), (d) hybridization with target, (e) hybridization with biotinylated detection probe, (f) association with avidin-alkaline phosphatase, (g) description of the process of the electrocatalytic reaction of />-aminophenol (p-AP) via electronic mediation of ferrocenyl dendrimer (Adapted from Ref. [160])... 

Specifically, the intermediate benzoxazole resin 32 was generated by treatment of aminophenol 33 with carbon disulfide and Merrifield resin 1 in the presence of triethy-lamine in acetonitrile, but the resin was obtained in very low yield under this condition. The inefficiency of this process is due to the rapid release of 2-mercaptobenzoxazole 34 from the intermediate 35 during the cyclization reaction (Scheme 10.6, path a). We attempted to circumvent this cleavage process by performing 2-mercaptobenzoxazole 34 however, reaction of aminophenol with carbon disulfide for 6h at 80 °C afforded 2-mercaptobenzoxazole 34 in a low yield (Scheme 10.6, path b). 

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