Synthesis of N-(Tosylmethyl)carbodiimides and Their Application in the Synthesis of 2-Amino-1,3-oxazoles from Aldehydes

Article abstract of DOI:10.1021/jo00323a018

A series of N-(tosylmethyl)carbodiimides (TosCH2N=C=NR¹, 3) have been prepared from the corresponding thioureas.Carbodiimides 3 with R¹ = triphenylmethyl or tert-butyl are useful synthons in a new one-step synthesis of 2-(alkylamino)-1,3-oxazoles 10 from aromatic aldehydes.Acid-induced removal of the triphenylmethyl group from 10 gives 2-amino-1,3-oxazoles (11).