thioimides

Thioimides are organic compounds composed of a carbonimidic acid group (-C(NH)-) connected to a thiophosphorus group (SPR), where R is an organic residue. These derivatives are formed by the reaction of isocyanides with thioimidoyl chlorides or thioimidoyl halides.

Thioimides exhibit distinct chemical properties due to the presence of the thiophosphorus group. They are more stable and less reactive compared to related species such as isothiocyanates and amidic acid derivatives. The thiophosphorus group can undergo various transformations, including arylation, alkylation, and substitution reactions, offering routes to functionalized thioimides.

Structural characteristics of thioimides can influence their reactivity. The ability to exhibit anomeric-like behavior has been observed in certain thioimides, resulting from the connection of the thiophosphorus group to an alkene or alkyne. In these instances, thioimides may manifest reactivities similar to those seen with S-C-unsaturated systems, such as pericyclic reactions and rearrangements.

Research has highlighted the relevance of thioimides in synthetic and applied chemistry, encompassing fields such as medicinal chemistry and materials science. Specific attention has been directed towards the potential therapeutic applications of thioimides in areas including anticancer and antimicrobial development, as a result of their unique structures being selectively recognized by cellular or enzymatic machinery.