202061-61-8Relevant academic research and scientific papers
An efficient one-pot synthesis of 3-aryl-5-methylisoxazoles from aryl aldehydes
Zhu, Shirong,Shi, Shuhao,Gerritz, Samuel W.
experimental part, p. 4001 - 4004 (2011/08/21)
An efficient protocol for the one-pot preparation of alkyl 3-aryl-5-methylisoxazole-4-carboxylates from aryl aldehydes is described. This method is readily amenable to the large scale preparation of isoxazoles as well as the parallel synthesis of isoxazole libraries.
Generation of nitroalkanes, hydroximoyl halides and nitrile oxides from the reactions of β-nitrostyrenes with Grignard or organolithium reagents
Yao, Ching-Fa,Kao, Kuo-Hsi,Liu, Ju-Tsung,Chu, Cheng-Ming,Wang, Yeh,Chen, Wen-Chang,Lin, Yu-Mei,Lin, Wen-Wei,Yan, Ming-Chung,Liu, Jing-Yuan,Chuang, Ming-Ching,Shiue, Jin-Lien
, p. 791 - 822 (2007/10/03)
The β-nitrostyrenes 1 or 2 react with Grignard or organolithium reagents in ether or THF solution to generate by 1,4-addition the intermediate nitronates A. When A is treated with dilute hydrochloric acid, high yields of the nitroalkanes 3 (and oximes 4) or 5 are obtained Hydroximoyl halides 6, 8 or nitrile oxides 7 can be isolated when the intermediate A is slowly added to the ice cold concentrated hydrohalic acid. The same products 6 and/or 7 are observed if the nitronates, generated from the substrate 1a, are added to 85% aqueous H2SO4 but only the hydrolyzed carboxylic acids 9 are generated when the β-nitrostyrenes 2 are reacted with Grignard reagents and worked up under the same condition. The nitrile oxides 7 can undergo 1,3-dipolar cycloaddition with alkenes or alkynes to generate 2-isoxazolines or isoxazoles. A one-pot synthesis of the [n,3,0] bicyclic (n = 3 or 4) compounds 23-27 by intramolecular nitrile oxide-olefin cycloadditions is reported.
A facile one-pot preparation of isothiocyanates from aldoximes
Kim, Jae Nyoung,Jung, Keum Shin,Lee, Hong Jung,Son, Ji Suk
, p. 1597 - 1598 (2007/10/03)
Isothiocyanates 2a-l were prepared in excellent yields in a one-pot reaction from aldoxime derivatives 1a-l by successive treatment of aldoxime with N-chlorosuccinimide (NCS), thiourea, and triethylamine. The use of HCl/DMF/Oxone system in the reaction instead of NCS was equally effective.
