55577-67-8Relevant academic research and scientific papers
Synthesis of 3-nitroindoles by sequential paired electrolysis
Lindsay, Ashley C.,Kilmartin, Paul A.,Sperry, Jonathan
, p. 7903 - 7913 (2021/09/28)
3-Nitroindoles are synthetically versatile intermediates but current methods for the preparation hinder their widespread application. Herein, we report that nitroenamines undergo electrochemical cyclisation to 3-nitroindoles in the presence of potassium iodide. Detailed control experiments and cyclic voltammogram studies infer the reaction proceedsviaa sequential paired electrolysis process, beginning with anodic oxidation of iodide (I?) to the iodine radical (I˙), which facilitates cyclisation of the nitroenamine to give a 3-nitroindolinyl radical. Cathodic reduction and protonation generates a 3-nitroindoline that upon oxidation forms the 3-nitroindole.
A Continuous-Flow, Two-Step, Metal-Free Process for the Synthesis of Differently Substituted Chiral 1,2-Diamino Derivatives
Pirola, Margherita,Compostella, Maria Elena,Raimondi, Laura,Puglisi, Alessandra,Benaglia, Maurizio
supporting information, p. 1430 - 1438 (2018/02/09)
The enantioselective organocatalytic reduction of aryl-substituted nitroenamines was successfully performed under continuous-flow conditions. After a preliminary screening with a 10-μL microreactor, to establish the best reaction conditions, the reduction was scaled up in a 0.5-mL mesoreactor, without appreciable loss of enantioselectivity, that remained constantly higher than 90%. The in-flow nitro reduction was also accomplished, either by Raney nickel catalyzed hydrogenation or by a metal-free methodology based on the use of the very inexpensive and readily available reducing agent trichlorosilane. The final aim is to develop a two-step, continuous-flow process for the stereoselective, metal-free, catalytic synthesis of differently functionalized chiral 1,2-diamines.
Highly enantioselective reduction of β-amino nitroolefins with a simple n-sulfinyl urea as bifunctional catalyst
Liu, Xiang-Wei,Yan, Yan,Wang, Yong-Qiang,Wang, Chao,Sun, Jian
supporting information; experimental part, p. 9204 - 9207 (2012/08/27)
Simple but effective: A structurally simple N-sulfinyl urea was found to be a highly efficient bifunctional catalyst, which allows for the development of a novel pathway for the construction of chiral β-amino nitroalkanes through enantioselective reduction of β-amino nitroolefins by trichlorosilane. High yields and excellent enantioselectivities were obtained for a broad range of β-arylamino nitroolefin substrates (see scheme). Copyright
