Preparative conversion of oximes to parent carbonyl compounds by cerium(IV) sulfate in acetonitrile and alcohol

A Convenient and Efficient One-Pot Synthesis of 3-Acylisoxazoles Using Iron(III) Salts

“…10 The 3-benzoylisoxazole derivatives have also become interesting key building blocks for drug candidates such as 3-[2-(2,5-dimethylphenoxymethyl)-a-methoxyiminobenzyl]isoxazole which possess potent fungicidal activity against crop diseases 11 and 3-(1-hydroxybenzyl)-5-dimethylaminomethylisoxazole methiodide, an antimuscarinic agents. 12 We have investigated many novel reaction systems using cerium salts 13 for selective oxidations. Although reactions with cerium salts proceeded smoothly, a reaction using non-toxic and inexpensive metal salts is required from an economic, practical, and environmental point of view.…”

“…We previously reported the structures of 2, 16-42, and 49-60 determined by spectral methods such as 1 H NMR, 13 C NMR, IR spectroscopy, EIMS, and HRMS. 9 In this paper, the structure of ethyl 3-benzoylisoxazolecarboxylate (59) was confirmed by X-ray analysis and the ORTEP drawing is shown in Figure 1.…”

“…The reaction conditions are shown in Tables 1-5. The spectral data (IR, 1 H NMR,13 C NMR, EIMS, CI-MS, and HRMS) of 3-acetylisoxazoles 2, 16-28, and 49-54 and 3-benzoylisoxazoles 29-42, 55-60 were reported in our previous paper 9. …”

Cerium (IV) sulfate: A highly efficient reusable heterogeneous catalyst for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones under solvent-free conditions

“…Recently cerium (IV) salts have been used for many organic transformations such as the synthesis of carboxylic esters from alkenes [26], synthesis of acetamido phenols [27], conversion of oximes into aldehydes and ketones [28], and one-pot synthesis of 3-acylisoxazoles or polyhydroquinolines [29,30]. The cerium (IV) salts act as Lewis acids in all of these reactions.…”