7064-02-0Relevant articles and documents
Synthesis of Isoxazolines and Oxazines by Electrochemical Intermolecular [2 + 1 + n] Annulation: Diazo Compounds Act as Radical Acceptors
Xiong, Mingteng,Liang, Xiao,Gao, Zhan,Lei, Aiwen,Pan, Yuanjiang
supporting information, p. 9300 - 9305 (2019/11/20)
Reported herein is an unprecedented synthesis of isoxazolines and oxazines through electrochemical intermolecular annulation of alkenes with tert-butyl nitrite, in which diazo compounds serve as radical acceptors. Notably, [2 + 1 + 2] and [2 + 1 + 3] annulations occur when styrenes and allylbenzenes are used as substrates, respectively. The latter reaction undergoes group migration to form more stable radical, manifesting radical route instead of conventional 1,3-dipolar cycloaddition occurs. Moreover, scale-up experiments suggest the potential application value of these transformations in industry.
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 (2017/06/23)
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.
Reactivity of the ester group attached isoxazoline, benzisoxazole, and isoxazole: A facial preparation of 3-acyl-substituted these heterocycles
Murai, Kenichi,Miyazaki, Shuji,Fujioka, Hiromichi
supporting information; experimental part, p. 3746 - 3749 (2012/10/07)
A facile preparation of 3-acyl-substituted isoxazolines, benzisoxazoles, and isoxazoles from the corresponding 3-carboxylate esters is described. The process, involving reaction of the ester derivative of 3-carboxylic acid substituted heterocycles with Gr