88636-53-7Relevant academic research and scientific papers
Formation of β-Oxo- N-vinylimidates via Intermolecular Ester Incorporation in Huisgen Cyclization/Carbene Cascade Reactions
Wang, Qinxuan,May, Jeremy A.
, p. 9579 - 9584 (2020)
Unusual intermolecular trapping of esters by carbenes generated via a Huisgen cyclization/retroelectrocyclization/dediazotization cascade reaction is presented. β-Oxo-N-vinylimidates could be obtained in one step from propargyl carbonazidates. Mechanistic control experiments suggested reversible dipole formation by ester addition to the carbene, and nitrogen attack to the ester carbonyl was irreversibly followed by stereoselective decarboxylative elimination to give the Z-vinyl imidate. The cross-conjugated enone, imidate, and enamine functional groups in the β-oxo-N-vinylimidates offer novel syntheses of functionalized oxazoles.
Synthesis of Oxazoles by the Reaction of Ketones with Iron(III) Solvates of Nitriles
Kotani, Eiichi,Kobayashi, Shigeki,Adachi, Mayumi,Tsujioka, Toshiyuki,Nakamura, Kouji,Tobinaga, Seisho
, p. 606 - 609 (2007/10/02)
Oxazoles having functionalized carbon substituents at the C-2 position were synthesized in one step by the oxidation of ketones with iron(III) solvates of nitriles, i.e., Fe(RCN)6(ClO4)3(solvate A) or Fe(RCN)6)FeCl4)3(solvate B), in the corresponding nitriles.Keywords oxazole; ketone; oxidation; nitrile; iron(III) nitrile solvate
