3672-49-9Relevant articles and documents
Tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes
Sau, Prasenjit,Santra, Sourav Kumar,Rakshit, Amitava,Patel, Bhisma K.
, p. 6358 - 6365 (2017)
A sequential construction of C-C, C-O, C = N, and C = O bonds from alkenes leading to the direct synthesis of isoxazolines in the presence of tert-butyl nitrite, quinoline, and the Sc(OTf)3 catalyst in DCE at 80 °C has been accomplished. An unprecedented three consecutive C-H functionalizations of two styrenes are involved in this isoxazoline synthesis. In this radical-mediated reaction, one-half of the aryl alkene is converted into an intermediate 2-nitroketone, which serves as a 1,3-dipolarophile and undergoes cycloaddition with the other half of the unreacted aromatic terminal alkene. The use of an alkyne in lieu of an alkene leads to the formation of isoxazole under identical reaction conditions.
1,2,5-Oxadiazole (Furazan) derivatives from benzoylnitromethane and dipolarophiles in the presence of DABCO: Structure and intermediates
Cecchi, Luca,De Sarlo, Francesco,Faggi, Cristina,Machetti, Fabrizio
, p. 3016 - 3020 (2006)
Furazan (1,2,5-oxadiazole) derivatives are obtained along with isoxazolines from the reaction of benzoylnitromethane with dipolarophiles in the presence of DABCO. Furazans are shown to derive from the intermediate dibenzoylfuroxan (3,4-dibenzoyl-1,2,5-oxa
Synthesis of 3-Acyl-Isoxazoles via Radical 5-endo trig Cyclization of β,γ-Unsaturated Ketones with NaNO2
Chen, Dengfeng,Huang, Shenlin,Jiang, Ping,Wang, Yaming,Zheng, Yu
, (2022/02/07)
Here we report a facile cyclization reaction of β,γ-unsaturated ketones with NaNO2 under mild conditions to construct 3-acyl-isoxazoles. This transformation is realized via nitrosation of the activated methylene, radical 5-endo trig cyclization
A Facile Approach to the Synthesis of 3-Acylisoxazole Derivatives with Reusable Solid Acid Catalysts
Itoh, Ken-Ichi,Hayakawa, Mamiko,Abe, Rina,Takahashi, Shinji,Hasegawa, Kenta,Aoyama, Tadashi
supporting information, p. 4636 - 4643 (2021/09/20)
Nitrile oxides were formed from nitro ketones using silica gel-supported sodium hydrogen sulfate (NaHSO4/SiO2) or Amberlyst 15 as solid acid catalyst, and then the corresponding 3-acylisoxaszoles were obtained by reacting with alkynes via the 1,3-dipolar [3+2] cycloaddition. These heterogeneous catalysts are easily separable from the reaction mixture and reused. This synthetic method provides a facile, efficient, and reusable production of 3-acylisoxazoles.
Iron Nitrate-Mediated Selective Synthesis of 3-Acyl-1,2,4-oxadiazoles from Alkynes and Nitriles: The Dual Roles of Iron Nitrate
Bian, Qilong,Wu, Cunluo,Yuan, Jiangpei,Shi, Zuodong,Ding, Tao,Huang, Yongwei,Xu, Hao,Xu, Yuanqing
supporting information, p. 4058 - 4066 (2020/04/10)
A direct strategy for the selective synthesis of 3-acyl-1,2,4-oxadiazoles from alkynes and nitriles has been developed under iron(III) nitrate-mediated conditions. The mechanism includes three sequential procedures: Iron(III) nitrate-mediated nitration of