Adamovskyi M. Expanding of the scope of Castagnoli–Cushman reaction

Thesis for a scientific degree of Doctor of Philosophy in specialty 102 – Chemistry (10 – Natural sciences). – Taras Shevchenko National University of Kyiv. – Taras Shevchenko National University of Kyiv, Kyiv, 2021. The thesis is connected with expanding of the scope of Castagnoli–Cushman reaction (CCR). This reaction is the interaction of cyclic anhydrides of dicarboxylic acids with imines. Lactams with the same cycle size that was in the anhydride are formed as a result of the reaction. The reaction products also contain a free carboxyl function suitable for further functionalization. The literature review, that contains 114 references, describes the importance of the Castagnoli-Cushman reaction among other multicomponent reactions. Products of the reaction are well-compatible with the concept of lead-like chemical space and are of interest to medical chemistry. In recent years there has been a significant increase in the number of publications on the topic, however the state of research is far from complete. The literature review includes references to classical research, but is mostly based on the latest developments of recent years. The first part of the literature review presents the possible mechanisms of this reaction, which were proposed. The types of anhydrides used in the reaction are described in the literature review next. Then possible types of imines and their analogues are described. A separate part of the literature review presents a stereoselective synthesis, including modern versions of catalytic asymmetric synthesis.