730964-72-4Relevant academic research and scientific papers
Triple role of phenylselenonyl group enabled a one-pot synthesis of 1,3-oxazinan-2-ones from α-isocyanoacetates, phenyl vinyl selenones, and water
Buyck, Thomas,Wang, Qian,Zhu, Jieping
, p. 11524 - 11528 (2014/10/15)
Reaction of α-substituted α-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.
New cleavable isocyanides for the combinatorial synthesis of α-amino acid analogue tetrazoles
Mayer, Josef,Umkehrer, Michael,Kalinski, Cédric,Ross, Günther,Kolb, Jürgen,Burdack, Christoph,Hiller, Wolfgang
, p. 7393 - 7396 (2007/10/03)
3-Substituted 3-isocyano propionates as new cleavable isocyanides in combinatorial tetrazole synthesis via Ugi-reaction are introduced. The obtained 5-substituted tetrazoles are transformed into carboxylic acid isosteric 5-substituted 1H-tetrazoles under basic cleavage conditions.
