104184-64-7Relevant articles and documents
Synthesis and conformational analysis of a ribo-type cyclohexenyl nucleoside
Vijgen, Sara,Nauwelaerts, Koen,Wang, Jing,Van Aerschot, Arthur,Lagoja, Irene,Herdewijn, Piet
, p. 4591 - 4597 (2005)
A straightforward approach to a novel class of ribo-type cyclohexenyl nucleosides is described. An electron-demand Diels-Alder reaction forms the key-step of the chosen synthetic pathway. Although the difference is small, conformational analysis using NMR shows that this nucleoside analogue adopts preferentially an 2H3 conformation (S-type), while the "deoxy" cyclohexenyl analogue has a preference for a C3′ endo conformation (N-type). Analyses of the conformational equilibrium reveal that, in the given experimental conditions, the difference between adenosine and its cyclohexenyl congener resides in their different ΔG values; furthermore, in adenosine, the conformational preference is of enthalpic origin, whereas in the cyclohexenyl congener, the conformational preference is of entropic origin.
A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds
Banwell, Martin G.,Jones, Matthew T.,Loong, David T.J.,Lupton, David W.,Pinkerton, David M.,Ray, Jayanta K.,Willis, Anthony C.
experimental part, p. 9252 - 9262 (2011/01/12)
The Pd[0]-catalyzed Ullmann cross-coupling of o-nitrohaloarenes 1a-e with the brominated heterocycles 2a-f delivers the expected products 3a-j in good to excellent yields. The reductive cyclization of such products, as well as N-acyl derivatives 3k, l, and m, has been investigated and provided the C-3 mono-substituted oxindoles 5a-d, f, g, k, and m, the direct reduction products 4i and j or indole 5l.
Electrochemical and yeast-catalysed ring-opening of isoxazoles in the synthesis of analogues of the herbicide Grasp
Easton,Heath,Hughes,Lee,Savage,Simpson,Tiekink,Vuckovic,Webster
, p. 1168 - 1174 (2007/10/03)
Isoxazoles substituted with an electron-withdrawing group at the 4-position undergo electrochemical and yeast-catalysed N-O bond cleavage. The electrolysis is much more efficient and, with acyl- and alkoxycarbonyl-substituted isoxazoles, it affords the enolised dicarbonylimine functionality characteristic of the herbicide Grasp. Regioisomeric 4- and 5-substituted isoxazoles are accessible through nitrile oxide cycloaddition chemistry, using halogen as a steric auxiliary to control the regiochemistry of reaction. Crystal data for compounds 11 and 19b are presented.
