85574-80-7Relevant academic research and scientific papers
Reaction of 2,2,6-Trimethyl-1,3-dioxin-4-one with Isoquinolinium and Pyridinium Ylides
Sato, Masayuki,Kanuma, Norio,Kato, Tetsuzo
, p. 4359 - 4364 (2007/10/02)
The reactions of diketene-acetone adduct (2,2,6-trimethyl-1,3-dioxin-4-one) (1) with heterocyclic ylides were investigated.Heating of the adduct with isoquinolinium bis(ethoxycarbonyl)methylide (3a) gave ethyl 1-acetyl-2-hydroxypyrroloisoquinoline-3-carboxylate (6a).Under similar conditions, isoquinolinium cyano(ethoxycarbonyl)methylide (3b) and phenacylide (3d) gave 1-acetyl-2-ethoxycarbonyloxypyrroloisoquinoline-3-carbonitrile (7) and 1-acetyl-3-benzoyl-2-hydroxypyrroloisoquinoline (6d), respectively.Isoquinolinium dicyanomethylide (3e) reacted with the adduct in a different manner to give bis(6-methyl-4-oxo-4H-1,3-oxazin-2-yl)methylide (8).Pyridinium ylides similarly reacted with the adduct to give indolizines and oxazinylmethylides.Keywords---diketene-acetone adduct; diketene: acetylketene; pyridinium methylides; isoquinolinium methylides; cycloaddition; pyrroloisoquinolines; indolizines; 1,3-oxazin-4-ones
