Search results for "Cyanohydrin"
showing 5 items of 5 documents
Two-Step Synthesis of 2-Aminoindolizines from 2-Alkylpyridines
2014
An efficient method for the synthesis of 2-aminoindolizines by the 5-exo-dig cyclization of 2-alkyl-1-(1-cyanoalkyl)pyridinium salts has been developed. These substrates were prepared by N-alkylation of 2-alkylpyridines with readily available cyanohydrin triflates. The method allows the introduction of various substituents at the 1-, 3-, 6-, 7-, and 8-positions and leaves no undesired acceptor groups in the products.
Preparation of 9a-Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities
2010
19 pages, figures, and tables statistics.
A Modular Synthesis of Polysubstituted Indolizines
2012
The N-alkylation of pyridines with cyanohydrin triflates or α-halonitriles furnishes 1-(1-cyanoalkyl)pyridinium salts that can react with nitroolefins under basic conditions to furnish polysubstituted indolizines. Overall, the indolizine core can be constructed from a pyridine, two aldehydes, and a nitroalkane, and no undesired functional groups remain in the products. When bromoacetonitrile was used for the N-alkylation, indolizine-3-carbonitriles were obtained instead. The pyridine component may be replaced by other azines, giving rise to related heterocyclic systems.
Synthesis of α-aminonitriles using aliphatic nitriles, α-amino acids, and hexacyanoferrate as universally applicable non-toxic cyanide sources
2018
In cyanation reactions, the cyanide source is often directly added to the reaction mixture, which restricts the choice of conditions. The spatial separation of cyanide release and consumption offers higher flexibility instead. Such a setting was used for the cyanation of iminium ions with a variety of different easy-to-handle HCN sources such as hexacyanoferrate, acetonitrile or α-amino acids. The latter substrates were first converted to their corresponding nitriles through oxidative decarboxylation. While glycine directly furnishes HCN in the oxidation step, the aliphatic nitriles derived from α-substituted amino acids can be further converted into the corresponding cyanohydrins in an oxi…
Programmed Formation of HCN Oligomers through Organosulfur Catalysis
2021
An efficient, inexpensive, and reliable synthesis of diaminomaleonitrile (DAMN, 1) is described starting from readily available acetone cyanohydrin as the source of hydrogen cyanide (HCN). Diaminomaleonitrile (DAMN) is known to be an important intermediate in heterocyclic and medicinal chemistry as well as being a possible precursor for the origin of life's hypothesis within prebiotic chemistry. The mechanism of its formation through organosulfur catalysis has been investigated by electrospray ionization mass spectrometry (ESI-MS) using two newly synthesized cationic "marker" molecules as a tool that allows for sensitive detection. As a result, the proposed mechanism of a thiocyanate-mediat…