γ-Cyanooxazolines: an interesting synthon from oxazoline cyanocuprate addition to conjugated cyanoalkenes

Facile synthesis of octahydrobenzo[h]isoquinolines: Novel and highly potent D1 dopamine agonists

“…Our approach was inspired by Simonelli and coworkers,40 who used lithiated 2,4,4-trimethyl-2-oxazoline to prepare γ amino acids. Realizing that unsaturated nitriles can serve as Michael acceptors for carbon nucleophiles,41,42 we envisioned that this method could be modified to prepare desired lactam 15 . That is, tetralone 7 was converted into unsaturated nitrile 9 by treatment with trimethylsilylcyanide and boron trifluoride etherate (Scheme 2).…”

Tin

“…55 (26) Reductions of aliphatic nitriles to the corresponding amines have been described with concomitant hydrolysis of an oxazolidinone function to the corresponding acid in a one-step procedure (eq 27). 57 Sterically hindered quaternary nitro groups could also be selectively and cleanly reduced to the corresponding amine (eq 28). This method was reported to be more efficient and selective compared to the traditional catalytic hydrogenation methods.…”