870-64-4Relevant articles and documents
Temperature controlled condensation of nitriles: Efficient and convenient synthesis of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines in one system
Li, Yinghua,Zhu, Yingzu,Xiang, Shiqun,Fan, Weibin,Jin, Jiang,Huang, Deguang
, p. 6576 - 6583 (2020/02/25)
A series of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines were synthesized by condensation of organonitriles in one system. A wide variety of compounds were obtained in good to excellent yields by simply controlling the reaction temperature. The base-induced transformation process is easy for production. The scope and versatility of the method have been successfully demonstrated with 72 examples. The flexible and diversified characteristics of nitriles were introduced based on electronic effect, steric effect, position of substituted groups and intermolecular hydrogen bonding. An updated reaction mechanism is proposed based on the study of the stoichiometric reaction conditions at variable temperature, and on the investigation of products with cis-trans configuration transformation.
Chemie der α-Aminonitrile. 1. Mitteilung. Einleitung und Wege zu Uroporphyrinogen-octanitrilen
Ksander, Gary,Bold, Guido,Lattmann, Rene,Lehmann, Christian,Frueh, Thomas,et al.
, p. 1115 - 1172 (2007/10/02)
Chemistry of α-Aminonitriles I: Introduction and Pathways to Uroporphyrinogen-octanitriles.An introduction to experimental studies on the chemistry of α-aminonitriles potentially relevant to the problems of prebiotic chemistry is presented.The framework of conditions wherein the investigations is chosen to be carried out implies both molecular oxygen and - whenever feasible - water to be excluded from reaction conditions.This study focusses on 2-amino-2-propenenitrile (3) (Scheme 6) as central starting material of reaction sequences which aim at the nitrile forms of proteinogenic amino acids as well as at the aza forms of building blocks of biological cofactor molecules as their targets (Scheme 5).Schemes 13, 16, 23 as well as 25, and 26 summarize reaction sequences by which 3 is tranformed within the definied framework of conditions into the thermodynamic (statistically controlled) mixture of the four isomeric uroporphyrinogen-octanitriles 57-60.HPLC's of such mixtures document the dominance of the least symmetrical isomer whose constitutional pattern of peripheral substituents happens to be the one present in all biological porphinoids.Preparative procedures for the synthesis of 3 (Scheme 9), the β,β-disubstututed pyrrol-nitriles 30, 53, and 54 (Scheme 19) as well as the porphyrinogen-octakis(propionitrile) and -octakis(acetonitrile) 65 and 66, respectively (Scheme 24) are given.