5,6-Dihydro-2(1H)-pyridinone

Intermediate 1 (41.6 g, 0.33 mol), 416 ml of dry toluene, Add second generation Grubbs catalyst 0.7g with stirring, Heated to 85 ~ 90 , the reaction was stirred for 7h, GC identification reaction end, the reaction is completed, cooled to room temperature, 8.5 ml of ammonia was added, stirred for 1 h, The filtrate was washed with water (3 × 30 ml), dried over anhydrous Na2SO4, filtered to remove the desiccant, concentrated to dryness under reduced pressure, the filtrate was added isopropyl ether 300ml, refluxed 20min, cooled to -5 ~ 0 standing 6h, filtered , The solid is washed with an appropriate amount of isopropyl ether, 24 g (Intermediate 2) of a white powdery solid, Yield 75percentTo a solution of 11 (0.125 g, 1 mmol) in anhydrous DCM (160 mL) was added Grubbs-II catalyst (42 mg, 5 mol percent) and stirred at reflux for 6 h. Then it was stirred for an additional 1 h at room temperature in open air to deactivate the catalyst. The reaction mixture was filtered through celite, concentrated, and the residue was purified by column chromatography on silica gel (60-120 mesh) using hexane/EtOAc (2:8) as an eluent to give brown liquid 70percent yield. To a solution of 8 (250 mg, 1 mmol) in anhydrous DCM (100 mL) was added Grubbs-II catalyst (100 mg, 6 mol percent) and stirred at reflux for 6 h. Then it was stirred for an additional 1 h at room temperature in the open air to deactivate the catalyst. The reaction mixture was filtered through celite, concentrated, and the residue was purified by column chromatography on silica gel using hexane/EtOAc (2:8) as an eluent to give brown liquid 70percent yield. Grubbs-II catalyst (42 mg, 5 mol percent) was added to a solution of 5 (0.125 g, 1 mmol) in anhydrous DCM (160 mL) and refluxed for 6 h under inert conditions. The mixture was stirred for an additional 1 h at room temperature in open air to deactivate the catalyst. The reaction mixture was filtered through celite, concentrated, and the residue was purified by column chromatography on silica gel using hexane/EtOAc (1:1) to give a brown liquid (52percent yield). General procedure: Method I (Grubbs I catalyst). The Grubbs I catalyst (5–10 mol percent) was added to adegassed homogeneous solution of diene amides 4a, 5a(1 mmol) in dry PhMe (5 ml) under inert atmosphere, andreaction mixture was heated at 80°C for 32 h. The reactionmixture was concentrated and purified by column chromatography, yielding a small amount of required lactamsalong with major part of starting diene amides.Method II (Grubbs II catalyst). Solution of diene amides4–6 a–f (1 mmol) in dry PhMe (5 ml) was degassed well, and Grubbs II catalyst (5–10 mol percent) was added under inertatmosphere. The resulting mixture was stirred at 80°C for14 or 32 h. The reaction mixture was concentrated andpurified on silica gel column using EtOAc–petroleum etheras eluent.

A new pyridone alkaloid as an intermediate in the synthesis of Piperlongumine (P482850).

Molecular Weight:97.12
XLogP3:0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:97.052763847
Monoisotopic Mass:97.052763847
Topological Polar Surface Area:29.1
Heavy Atom Count:7
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes