Strecker reaction and α-amino nitriles: Recent advances in their chemistry, synthesis, and biological properties

alpha-Amino nitrile compounds have a profound impact on bio-chemical sciences, as they have been prepared from inexpensive starting materials and have become valuable intermediates in the chemical synthesis of vitally important heterocyclic and carbocyclic molecules, which serve as suitable models in pharmacological and biological research. The alpha-amino nitrile moiety has been found in the structure of different alkaloids, while the alpha-amidoacetonitrile group is an essential fragment of new anti hyperglycemic drugs and promising pharmacological and agrochemical agents. Due to their synthetic, biological and practical importance, this review highlights the recent information about the preparation of alpha-amino nitriles through the Strecker-type and alpha-cyanation reactions, their chemical and biological properties, as well as their synthetic application, paying attention on the wonderful capacity for generating novel molecular diversity for pharmacological, biological and agrochemical researches, which ends with the total synthesis of complex alkaloids, preparation of new N-heterocycles and alpha-amino-nitrile-containing drugs. Analyzing modern synthetic protocols for the Strecker-type reactions and cyanation reactions based on cross-dehydrogenative coupling (CDD) process, the advantages and disadvantages of new catalysts and green reaction conditions are also discussed. In addition, remarkable biological properties of alpha-amidoacetonitrile derivatives as potent and selective protease inhibitors as well as promising pesticidal agents were briefly reviewed. The bibliography includes 461 references. (C) 2018 Elsevier Ltd. All rights reserved.