Simple synthesis of 3-acyl-5-alkyl(aryl)isoxazoles from terminal alkynes and nitrates of alkaline metals or ammonium

A simple and general synthesis of 3-acyl-5-alkyl(aryl)isoxazoles by reaction of terminal alkynes with nitrates in acetic acid in the presence of SO3 or alkaline salts is described.

[1]  Ki-Whan Chi,et al.  Halogenating and Nitrating Activity of Reagents Based on Sodium Nitrate and Alkali Metal Halides in Acetic Acid , 2004 .

[2]  C. A. Horiuchi,et al.  A novel one-pot synthesis of 3-acetyl- and 3-benzoylisoxazole derivatives using ammonium cerium nitrate (CAN) , 2002 .

[3]  M. Yusubov,et al.  New Reaction of Terminal Acetylenes with Nitrates in the Presence of Sulfur Trioxide: Heterocyclization into 3-Acyl-5-Aryl(Alkyl)Isoxazoles , 2001 .

[4]  E. Cereda,et al.  Solid-phase synthesis of 3-hydroxymethyl isoxazoles via resin bound nitrile oxides , 2001 .

[5]  M. Yusubov,et al.  A Novel Practical Reaction of Diarylalkynes With Sulfur Trioxide: Oxidation to 1,2-Diketones , 2001 .

[6]  M. Yusubov,et al.  Unexpected Formation of E-1-Methylthio-1,2-diphenyl-2-chloroethene in Reaction of Diphenylacetylene with DMSO in the Presence of Sulfur Trioxide and CCl4. , 2000 .

[7]  M. Yusubov,et al.  Reaction of Phenylacetylene with Sulfuric Acid or Sulfuric Anhydride. Synthesis of 4,6-Diphenyl-1,2-oxathiin 2,2-Dioxide. , 1999 .

[8]  O. Yurchenko,et al.  Reaction of Acetylenic Hydrocarbons with Dimedone and Some α-Nitroketones. , 1998 .

[9]  Ki-Whan Chi,et al.  A Facile Synthesis of α-Iodo-β-nitroalkenes from Alkynes Using I2/NO3- or KI/NO3-. , 1998 .

[10]  Ki-Whan Chi,et al.  A Facile Synthesis of α -Iodo- β -nitroalkenes from Alkynes Using I2/NO3 − or KI/NO3 − , 1998 .

[11]  E. Steckhan,et al.  Oxidative free-radical additions of α-nitro ketones and α-nitro amides to alkenes and alkynes mediated by electrochemically regenerable manganese(III) acetate , 1994 .

[12]  F. Gasparrini,et al.  Gold(III)-catalyzed one-pot synthesis of isoxazoles from terminal alkynes and nitric acid , 1993 .