24334-54-1Relevant academic research and scientific papers
Copper-catalyzed oxidative cleavage of Passerini and Ugi adducts in basic medium yielding α-ketoamides
Ghoshal, Anirban,Ambule, Mayur D.,Sravanthi, Revoju,Taneja, Mohit,Srivastava, Ajay Kumar
, p. 14459 - 14474 (2019/10/01)
The aerobic oxidative cleavage of Passerini and Ugi adducts in the presence of base and copper(i) iodide is studied in detail. The oxidative cleavage yields α-ketoamides along with acids and amides from Passerini and Ugi adducts respectively. Mechanistic investigations revealed that the reaction proceeds via a radical pathway involving molecular oxygen. Control experiments with 18O-labeled Passerini adducts confirmed that molecular oxygen is the source of oxygen in α-ketoamides. A variety of Passerini and Ugi adducts were studied to explore the effect of substitution. Overall, the present study provides an insight into the reactivity of Passerini and Ugi adducts in strong basic conditions along with a method to prepare α-ketoamides.
A new modification of the Passerini reaction: A one-pot synthesis of α-acyloxyamides via sequential Kornblum oxidation/Passerini reaction
Adib, Mehdi,Sheikhi, Ehsan,Azimzadeh, Marjan
, p. 1933 - 1936 (2015/03/30)
Abstract A novel approach for the synthesis of α-acyloxyamides is described. Benzylic substrates (halides or tosylates), under mild Kornblum conditions, are oxidized to give the corresponding aldehydes, which undergo a Passerini reaction with carboxylic acids and isocyanides to produce the corresponding α-acyloxyamides in excellent yields.
Novel Synthesis of the Mesoionic System 1,3-Oxazolium-4-olate
Haddadin, Makhluf J.,Kattan, Asma M.,Freeman, Jeremiah P.
, p. 723 - 725 (2007/10/02)
Thermolysis or photolysis of N-phenyldibenzoylnitrone (1) produces N-benzoylphenylglyoxanilide (5) and not the previously reported oxaziridine 2.Treatment of imide 5 with triethyl phosphite produced 2,3,5-triphenyl-1,3-oxazolium-4-olate (8), a new member
