New synthesis of N-sulfinyl compound and its application for organic synthesis

Abstract

N-Sulfinyl compounds have been widely studied and known to be very important heterocumulenes having a sulfur-centered structure of great synthetic utility. A new facile synthesis of N-sulfinyl compounds using N,N``-sulfinylbisimidazole(NSI) and N-(chlorosulfinyl) imidazole(NCI) was studied. Treatment of amine and its derivatives such as amines, amides, and sulfonamides with NSI and NCI, respectively, gives the corresponding N-sulfinyl compounds in quantitative yields under the mild conditions. NCI is a better reagent for the preparation of N-sulfinyl compounds. A new reaction of $\alpha$-hydroxy acids with N-sulfinylanilines has been studied. N-Sulfinylanilines react with $\alpha$-hydroxy acids to give $\alpha$-hydroxy anilides in quantitative yields under the mild conditions. The amidation reaction appears to involve intermolecular catalysis by the carboxyl group and intramolecular catalysis by the hydroxyl group.