Cyclic acyl amidines as unexpected C4-donors for fully substituted pyridine ring formation in the base mediated reaction with malononitrile
A new one-step, pseudo four-component approach for the synthesis of fully substituted pyridines via ring-opening of the cyclic acyl amidine of 3-amino-1H-isoindol-1-one and its aza-analogues during the reaction with malononitrile in the presence of sodium methoxide, followed by pyridine ring closure is reported. This method allows the one-step preparation of previously unknown 2-(pyridin-4-yl)(hetero)aryl carboxamides in good yields under mild reaction conditions.
Tkachuk, Volodymyr,Merkulova, Vladyslava,Omelchenko,Arrault, Axelle,Hordiyenko, Olga
supporting information
p. 1959 - 1963
(2019/06/27)
Nucleophically transformed N-heterocyclic nitriles trapped by cyanooxomolybdates(IV): Crystallographic and spectroscopic study
The reaction of K3Na[Mo(CN)4O2] ·6H2O with 2,3-dicyanopyrazine or 2-pyridinecarbonitrile in aqueous media results in isolation of two new compounds of formulae (PPh 4)2[Mo(CN)3O(pzac)]·2H2O (Hpzac = 3-carbamoyl-2-pyrazinecarboxylic acid) and (PPh4) 2[Mo(CN)3O(pynccn)]·3H2O·EtOH (Hpynccn = 2-pyridineiminocarbonitrile) respectively. X-ray single crystal structure measurements as well as physicochemical measurements confirm transformations of 2,3-dicyanopyrazine to 3-carbamoyl-2-pyrazinecarboxylic acid and 2-pyridinecarbonitrile to 2-pyridineiminocarbonitrile. All complexes are characterized by elemental analysis, IR and UV-Vis spectroscopy. Metal-assisted ligand transformations are studied spectrophotometrically in the pH range 8.5-11.5. Two different pathways of nitrile reactivity are shown and discussed.
Ryniewicz, Anna,Tomecka, Monika,Szklarzewicz, Janusz,Matoga, Dariusz,Nitek, Wojciech
p. 229 - 237,9
(2020/07/31)
PREPARATION AND STRUCTURAL ASSIGNMENTS OF SOME ISOMERIC 2,3-DISUBSTITUTED PYRIDINES
The preparation of several isomeric 2,3-disubstituted pyridine compounds are described and their spectroscopical data given.IR and NMR spectra of quinolinimide, reported by Distefano et al., are contradicted.The electron impact mass spectra are found to be useful in the differentiation between positional isomers.
Spiessens, Luc I. M.,Anteunis, Marc J. O.
p. 205 - 232
(2007/10/02)
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