Synthesis Of 1-Mono-and 1,1-Disubstituted Taurines From Nitroolefins

Taurine is an essential sulfur-containing amino acid due to its various physiological functions.It has been widely used in clinical and food additives. Some substituted taurines also show importantly physiological activity. Thus, it is desired to develop the efficient and practical synthetic methods for substituted taurines.Although several methods have been documented for the synthesis of 1-mono-and 1,1-disubstituted taurines, all of them are not versatile for aliphatic and aromatic 1-mono-and 1,1-disubstituted taurines.A versatile and practical synthesis of 1-mono-and 1,1-disubstituted taurines has been developed in this dissertation.A series of nitroolefins were prepared from aldehydes,ketones,or olefins by some convenient methods.They underwent the nucleophilic addition reaction with sodium ethylxanthan to give rise to nitroalkyl xanthates in satisfactory to good yields.After the oxidation with performic acid and subsequent reduction with hydrogen in the presence of Pd/C, the nitroalkyl xanthates were converted to 1-mono and 1,1-disubstituted taurines in moderate overall yields.The current method can be used to synthesize both aliphatic and aromatic 1-mono-and 1,1-disubstituted taurines. The method is indeed a versatile and practical route to the synthesis of 1-mono-and 1,1-disubstitued taurines because of readily available starting materials, good overall yields, short synthetic steps, and salt-free process.