83325-65-9Relevant academic research and scientific papers
Squaramide-Catalyzed Synthesis of Enantioenriched Spirocyclic Oxindoles via Ketimine Intermediates with Multiple Active Sites
Sun, Qiang-Sheng,Zhu, Hua,Chen, Yong-Jian,Yang, Xiao-Di,Sun, Xing-Wen,Lin, Guo-Qiang
, p. 13253 - 13257 (2015)
A new method for the construction of five-membered spirocyclic oxindoles is based on a Michael-Mannich cascade reaction of a ketimine intermediated catalyzed by a bifunctional quinine-derived squaramide. The desired products were obtained in excellent yie
Nitrone/Imine Selectivity Switch in Base-Catalysed Reaction of Aryl Acetic Acid Esters with Nitrosoarenes: Joint Experimental and Computational Study
Volpe, Chiara,Meninno, Sara,Roselli, Angelo,Mancinelli, Michele,Mazzanti, Andrea,Lattanzi, Alessandra
supporting information, p. 5457 - 5466 (2020/10/12)
Herein we report a mild and diastereoselective access to ketonitrones by reacting easily available aryl acetic acid esters and other active methylene compounds, with nitrosoarenes under catalytic loading of 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) at room temperature. Depending on the substitution pattern and nature of the aryl moiety, a switch toward the formation of imines can be observed. The mechanistic framework is put to scrutiny by experimental and theoretical studies, pointing to the formation of a nitroso aldol intermediate, whose fate toward one of the competing pathways, namely hydride transfer or elimination, would depend upon the NOH/CHα relative acidities. (Figure presented.).
CONJUGATED SCHIFF'S BASES-14; CYCLOADDITION OF HETEROCUMULENES TO SOME 1-OXA-4-AZABUTADIENES
Moskal, Janusz,Moskal, Alexandra,Milart, Piotr
, p. 1787 - 1792 (2007/10/02)
1-Oxa-4-azabutadienes proved to be prone to react with some heterocumulenes after 1,3-cycloaddition patterns yielding various 5,5-disubstituted derivatives of 1,3-diaryl-hydanotoins as it was shown by the chemical and spectroscopic analysis.Relatively high yields, mild reaction conditions and a very weak effect of solvent polarity on the reaction rate suggested a synchroneous mechanism involving 1,2-migration of a substituent.
