454466-62-7Relevant academic research and scientific papers
Gold(III)-catalyzed chemoselective annulations of anthranils with N-allylynamides for the synthesis of 3-azabicyclo[3.1.0]hexan-2-imines
Song, Lina,Tian, Xianhai,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 9007 - 9010 (2019/08/01)
We herein report the gold(iii)-catalyzed selective annulation of anthranils with N-allylynamides under mild conditions. By trapping the in situ-generated α-imino gold carbenes, 3-azabicyclo[3.1.0]hexan-2-imines were obtained in high synthetic efficiency. The reaction, which can be conducted in the gram scale, tolerates electron-rich and electron-deficient anthranils as well as a diverse set of functionalized ynamides (aryl- and alkyl-substituted terminal).
One-pot synthesis of 2,1-benzisoxazoles (anthranils) by a stannous chloride-mediated tandem reduction-heterocyclization of 2-nitroacylbenzenes under neutral conditions
Chauhan, Jay,Fletcher, Steven
supporting information, p. 4951 - 4954 (2012/11/07)
Classically, 2,1-benzisoxazoles (anthranils) are prepared from 2-nitroacylbenzenes by a reductive heterocyclization reaction with Sn or SnCl2 concentrated HCl. Acid sensitive functionalities are expected to be incompatible with these conditions; milder approaches to the synthesis of 2,1-benzisoxazoles would be welcomed. We demonstrate that SnCl 2·2H2O in a 1:1 mixture of EtOAc/MeOH is capable of mediating the tandem reduction-heterocyclization of a variety of 2-nitroacylbenzenes to their corresponding 2,1-benzisoxazoles in good to excellent yields under essentially neutral conditions. Importantly, several commonly used acid-labile protecting groups, including Boc carbamate, tert-butyl ether, and tert-butyl ester, proved orthogonal to these reaction conditions.
A novel cyclization to isoxazolo[3,4-e][2,1]benzisoxazole
Katritzky, Alan R.,Wang, Zuoquan,Hall, C.Dennis,Ji, Yu,Akhmedov, Novruz G.
, p. 3449 - 3451 (2007/10/03)
Methylation of 2,1-benzisoxazole 4,5-dione 4-oxime 2 using dimethyl sulfate in DMF and in the presence of potassium carbonate gave a substantial yield of isoxazolo[3,4-e][2,1]benzisoxazole 4 by an unexpected cyclization reaction of the O-methylation product 3.
