The behavior of 2-thioxo-4-thiazolidinones toward organophosphorus reagents

Abstract

The reaction of 2-thioxo-4-thiazolidinone (1a) with phosphorus ylides 2a and 2b afforded compounds 5 and 6. On the other hand, formylmethylenetriphenylphosphorane (2c) reacts with 1a and its N-methyl derivative 1b to give the new complicated phosphonium ylides 7a,b, respectively. Reactions of 1b with ylides 2a and 2d gave rise to the olefinic compound 8 and the new phosphorane product 9. Moreover, dialkyl phosphites 3a,b and trialkyl phosphites 4a-c react with 1a to give both the alkylated products 10a-c and the dimeric compounds 11,12. A mechanism is proposed to explain the formation of the new products. © 1999 John Wiley & Sons, Inc.