31562-30-8Relevant articles and documents
Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes
Kadam, Kishorkumar S.,Gandhi, Thirumanavelan,Gupte, Amol,Gangopadhyay,Sharma, Rajiv
, p. 3996 - 4008 (2016/11/11)
An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of E and Z) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either tert-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent in situ [3+2] dipolar cycloaddition to the substituted alkynes to give 3,5-disubstituted isoxazoles regioselectively in high to excellent yields. The developed synthetic methodology was applied for the synthesis of a previously reported potent hDGAT1 inhibitor.
Regioselective synthesis of C-nucleosides by 1,3-dipolar cycloaddition of arylnitrile oxides to 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose
Al-Timari, Usama A. R.,Fisera, Lubor
, p. 121 - 127 (2007/10/02)
The synthesis of 3-aryl-5-(1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-2-isoxazoline (3) from arylnitrile oxides and 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose (1) is described.The 1,3-dipolar cycloaddition reactions give mainly anti-adducts (>=95percent ?-facial stereoselectivity).
REACTIONS OF NITRILE OXIDES WITH NITROGEN OXIDES. 2. REACTIONS WITH NITROGEN MONOXIDE AND NITROGEN SESQUIOXIDE
Rakitin, O. A.,Ogurtsov, V. A.,Godovikova, T. I.,Khmel'nitskii, L. I.
, p. 1472 - 1474 (2007/10/02)
We have studied the reactions of aromatic nitrile oxides with nitrogen monoxide and nitrogen sesquioxide.It was shown that the nitrogen monoxide removes an oxygen atom from the nitrile oxide with formation of the corresponding nitrile and nitrogen dioxide.The reaction products with nitrogen sesquioxide are formed as a result of reactions of the nitrile oxide with nitrogen monoxide and nitrogen tetroxide.