An enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived: N -Boc ketimines
By employing a chiral phosphoric acid as a catalyst, an enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived N-Boc ketimines was realized. The reaction provided a wide variety of novel 3-isoxazole 3-amino-oxindoles with good yields (up to 99%) and moderate to good enantioselectivities (up to 99%). The absolute configuration of one product was assigned by X-ray crystal structural analysis and a plausible reaction mechanism was proposed. In addition, a scale-up reaction was performed successfully. Finally, one product was subjected to Suzuki-Miyaura coupling with phenylboronic acid to afford the product in a moderate yield without erosion of the enantioselectivity. This journal is
Liu, Hui,Yan, Yingkun,Li, Min,Zhang, Xiaomei
supporting information
p. 3820 - 3824
(2021/05/14)
Reactions of 5-Aminoisoxazoles with α-Diazocarbonyl Compounds: Wolff Rearrangement vs N-H Insertion
A highly chemoselective reaction between 5-aminoisoxazoles and α-diazocarbonyl compounds has been described. Both Wolff rearrangement and N-H insertion products can be obtained selectively by the judicious choice of reaction conditions. In the case of the
Hoveyda-Grubbs II Catalyst: A Useful Catalyst for One-Pot Visible-Light-Promoted Ring Contraction and Olefin Metathesis Reactions
A one-pot reaction to synthesize functionalized 2H-azirines through visible-light-mediated ring contraction and olefin metathesis of isoxazoles is described. Hoveyda-Grubbs II catalyst was found to function as a photocatalyst for these transformations, al
A modified procedure for the synthesis of 5-amino-3-arylisoxazoles and their reactions with tetrasulfur tetranitride antimony(V) chloride complex (S4N4·SbCl5): Novel synthesis of 3-aryl-1,2,5-thiadiazole-4-carboxamides
Dropwise addition of α-bromo ketoximes to a solution of KCN in MeOH at room temperature gave 5-amino-3-arylisoxazoles in moderate to good yields. Treatment of the isoxazoles prepared with tetrasulfur tetranitride antimony (V) chloride complex (S4N4·SbCl5) in toluene at 100°C afforded novel 3-aryl-1,2,5-thiadiazole-4-carboxamides.
Kong, Yung Cheol,Kim, Kyongtae,Park, Yung Ja
p. 75 - 89
(2007/10/03)
1-Benzoyl-3-(isoxazolyl or benzisoxazolyl)-ureas and insecticidal use thereof
The present invention is directed to 1-(benzoyl)-3-(isoxazolyl or benzisoxazolyl)urea or thiourea compounds useful as insecticides.
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(2008/06/13)
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