Synthesis of five-membered heterocycles containing a nitrogen-oxygen bond via O-acylation of aliphatic nitro compounds.
作者： KAZUHO HARADA , EISUKE KAJI , SHONOSUKE ZEN
DOI: 10.1248/CPB.28.3296
关键词:
摘要: O-Acylation of primary aliphatic nitro compounds with acid chlorides in N, N-dimethylacetamide led to the formation nitrile oxides, which cyclized situ olefinic dipolarophiles a 1, 3-dipolar cycloaddition mode afford 2-isoxazoline derivatives. Optimum reaction conditions were investigated, and use several types dipolarophiles, such as acetylenes, Schiff bases, aromatic nitriles, ketones, this resulted corresponding cycloadducts, namely isoxazoles, 2, 4-oxadiazolines, 4-oxadiazoles, 4, 2-dioxazoles, respectively, reasonable yields.
sci-hub.se 参考文章(4)
Zvi Rappoport, The chemistry of the cyano group ,(1970)
Saul Patai, The Chemistry of double-bonded functional groups ,(1989)
Henry Feuer, The chemistry of the nitro and nitroso groups Interscience Publishers. ,(1969)
Eisuke Kaji, Akira Igarashi, Shonosuke Zen, The Synthetic Reactions of Aliphatic Nitro Compounds. XI. The Synthesis of β-Amino-α-hydroxycarboxylic Acids and γ-Aminocarboxylic Acids Bulletin of the Chemical Society of Japan. ,vol. 49, pp. 3181- 3184 ,(1976) , 10.1246/BCSJ.49.3181