Stable thioaldehydes: Synthesis, structure assignment, and stability of 6-amino-5-thioformyluracils

Article abstract of DOI:10.1016/0040-4020(96)00533-9

Stable 6-amino-5-thioformyluracils 3a-e were synthesized starting from 6-amino-1,3-disubstituted uracils 1a-e in 23-98% yields. According to the X-ray crystal structure, although the thioaldehyde 3c possesses reasonable double-bond character of the C=S bond, the length of C=S bond of the thioaldehyde 3c is longer than those of the kinetically stabilized thioaldehydes due to the mesomeric effect of the 6-amino group.