139995-93-0Relevant 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.
Intramolecular 1,3-dipolar cycloaddition of nitrile N-oxide accompanied by dearomatization
Yonekawa, Morio,Koyama, Yasuhito,Kuwata, Shigeki,Takata, Toshikazu
, p. 1164 - 1167 (2012/03/27)
Intramolecular 1,3-dipolar cycloaddition of 2-phenoxybenzonitrile N-oxides to benzene rings, accompanied by dearomatization, formed the corresponding isoxazolines in high yields. The X-ray single-crystal structure analysis revealed that the reaction formed the cis-adduct as a single isomer. The substituents on the benzene rings markedly affected the reaction rate, yield, and structure of the final product.
Process for producing alkoxyiminoacetamide compounds and intermediates
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, (2008/06/13)
A compound of the formula [I] STR1 wherein X is hydrogen, lower alkyl, lower alkoxy or halogen; R is lower alkyl; and ? is any configuration of E-isomer, Z-isomer or a mixture thereof is produced by reacting a compound of the formula STR2 wherein X and ?