ActivitiesAssociate Professor Nishikata has succeeded in controlling the reactivity of oxygen and nitrogen in amide groups – The achievement of the free and separate creation of lactam and iminolactone! - 2016.11.24
Amide groups are important functional groups for synthesizing heterocyclic molecules that form pharmaceutical products and agricultural chemicals. In fact, there have to date been many reported examples of papers that have used amide reactivity. However, there has been no example in which the reaction sites of the nitrogen and oxygen in an amide functional group have successfully been freely controlled by means of differences in reaction conditions. If these reactivities can be controlled, it will make it possible to synthesize lactam and iminolactone from the same starting material. Therefore, development of an amide reactivity control method has been sought for many years.
This time, Associate Professor (tenure track) Takashi Nishikata and colleagues at the Graduate School of Sciences and Technology for Innovation (Applied Chemistry Field) have found that when an α-bromoimide compound is made to react with an acrylic acid derivative in the presence of a copper catalyst, only the nitrogen’s reactivity is expressed under strong base conditions, and the corresponding iminolactone is produced. On the other hand, when the reaction is carried out under weak base conditions, this time only the oxygen in the amide reacts, and the conversion is to the corresponding iminolactone.
These research results ACS Catalysis were published in
As a methodology for chemically precise control of the reactivity of an amide functional group, future applications are anticipated in the field of heterocyclic chemistry.