Deamination of 2-aminothiazoles and 3-amino-1,2,4-triazines with nitric oxide in the presence of a catalytic amount of oxygen
2-Aminothiazoles, 2-aminobenzazoles, and 3-amino-1,2,4-triazines were deaminated using nitric oxide (NO) in the presence of a catalytic amount of oxygen to afford corresponding unsubstituted heterocycles in good yields.
Formation of ?-Anionic Complexes in Reactions between 5-Nitrothiazole, 6-Nitrobenzothiazole and Tetrabutylammonium Borohydride
The title reactions were performed in toluene, tetrahydrofuran (THF) and dimethylsulfoxide. 1H NMR spectral data from the reaction mixtures in Me2SO and in THF indicate that each substrate affords only one respective ?-anionic complex.Kinetic data on formation of the complexes indicate that the attack of the nuclophile and stability of the complexes are affected greatly by changing the solvent.In agreement with our previous findings, in Me2SO the rate of formation of the complexes from both substrates considered is lower than that observed in less polar solvents (toluene and THF).The explanation of this trend includes comparison of charge dispersion in the transition state with respect to the initial state and the possibility of changes in the hydride ion carrier when the solvent is changed.
Forlani, Luciano,Ferrara, Antonio,Lugli, Andrea,Todesco, Paolo E.
p. 1703 - 1708
(2007/10/02)
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