Application of Acrolein Imines to Organic Synthesis, Biofunctional Studies, and Clinical Practice

Abstract

N‐alkyl unsaturated imines derived from acrolein, a toxin produced during oxidative stress, and biogenic alkyl amines occur naturally and are considered biologically relevant compounds. However, despite the recent conceptual and technological advances in organic synthesis, research on the new reactivity of these compounds is lacking. This personal account discusses research on the reactivity that has been overlooked in acrolein imines, including the discovery of new methods to synthesize biologically active compounds, the determination of new functions of relevant imines and their precursors, i. e., aldehydes and amines, and the application of these methods for clinical diagnosis.

Donor–Acceptor Mixed-Naphthalene Diimide-Porphyrin MOF for Boosting Photocatalytic Oxidative Coupling of Amines

“…Imines, as an important class of versatile intermediates that bear the CN bond, have been widely utilized in the synthesis of quinolines, cucurbiturils, and oxaziridines, which are of significant importance in agricultural, pharmaceutical, and synthetic chemistry. − Traditionally, imines are commonly prepared via the condensation reactions of primary amines with aldehydes or ketones, generally requiring dehydrating agents (i.e., molecular sieves and strong acids), high temperature, as well as expensive catalysts (i.e., Sheppard amidation reagent) to push the reaction equilibrium for product formation. − Furthermore, these synthetic protocols usually not only lead to unsatisfactory selectivity and poor functional group tolerance but also need complex post-treatment purification processes to remove the byproducts, dehydrating agents, and catalyst residuals. Therefore, it is particularly desirable to develop mild, green, and sustainable methods for the synthesis of imines and promote their applications in pharmaceutical and biotechnological industries.…”