Treatment of 6-(3-phenyl-2-hydroxypropyl)-4,5-dihydro-3(2-pyridazinones 6a–c with trimethylsilyl triflate (TMST) in refluxing dichloromethane gave the unexpected 3-(1-naphthyl)propionic acid ethyl ester derivatives 9a–c. The isolation of the spirotetrahydropyridazinone intermediate 5 suggest, as a plausible reaction mechanism, an intramolecular aminoalkylation key step, followed by ring opening and elimination of hydrazine and water also promoted by TMST.
An unusual trimethylsilyltriflate catalyzed transformation of 6-[3-aryl-2-hydroxypropyl]-4,5-dihydro-3(2H)-pyridazinones into 3-(1-naphthyl)propionic acid esters
BARALDI, Pier Giovanni;MANFREDINI, Stefano;SIMONI, Daniele;
1993
Abstract
Treatment of 6-(3-phenyl-2-hydroxypropyl)-4,5-dihydro-3(2-pyridazinones 6a–c with trimethylsilyl triflate (TMST) in refluxing dichloromethane gave the unexpected 3-(1-naphthyl)propionic acid ethyl ester derivatives 9a–c. The isolation of the spirotetrahydropyridazinone intermediate 5 suggest, as a plausible reaction mechanism, an intramolecular aminoalkylation key step, followed by ring opening and elimination of hydrazine and water also promoted by TMST.File in questo prodotto:
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