Highly chemoselective acylation of substituted aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione

Article abstract of DOI:10.1016/0040-4020(95)00783-5

A general procedure for chemoselective acylation of substituted aminophenols has been developed. The N-acetylated products 7 and 10a-h were prepared by treating the aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione (1) in refluxing THF in 70-100% yield. The esters 8 and 13d,b,j of 3- and 4-amino phenols could be obtained in 70-94% yield by treating with NaH and 1.