19625-63-9Relevant articles and documents
Cu-Catalyzed switchable synthesis of functionalized pyridines and pyrroles
Ling, Zheng,Xie, Fang,Gridnev, Ilya D.,Terada, Masahiro,Zhang, Wanbin
, p. 9446 - 9449 (2018)
Herein, we describe a high yielding and switchable synthesis of a range of functionalized pyridines and pyrroles via Cu-catalyzed cascade reactions with alkynes and N-sulfonyl azadienes which are readily available from saccharin. Both unsymmetrical 2,4,6-trisubstituted pyridines and multi-substituted pyrroles could be transformed into some bioactive compounds and chiral ligands.
Access to 4,6-Diarylpicolinates via a Domino Reaction of Cyclic Sulfamidate Imines with Morita-Baylis-Hillman Acetates of Nitroolefins/Nitrodienes
Majee, Debashis,Biswas, Soumen,Mobin, Shaikh M.,Samanta, Sampak
, p. 4378 - 4385 (2016/06/09)
An interesting domino reaction of 5-membered cyclic sulfamidate imines with a variety of Morita-Baylis-Hillman acetates of nitroolefins/nitrodienes in the presence of DABCO as an organic base at 55 °C is reported for the first time. This new synthetic strategy provides a series of pharmacologically interesting 4,6-diarylpicolinates in high to excellent yields and allows several compatible functionalities on aryl rings. Moreover, the biologically interesting imidazo[1,2-a]pyridine (alpidem derivative) has been prepared in high chemical yield through a unique procedure.
Nucleophilic Displacements of N-Aryl and Heteroaryl Groups. Part 3. Pyrylium-mediated Synthesis of Unsymmetrical Diarylamines from Anilines
Katritzky, Alan R.,Cozens, Andrew J.
, p. 2611 - 2615 (2007/10/02)
2-Ethoxycarbonyl-4,6-diphenylpyrylium salts (1) reacted with various ring-substituted anilines to give the corresponding pyridinium salts (2) (average yield 90percent); these were hydrolysed to the pyridinium betaines (3) (75percent) and treated with thionyl chloride followed by an aniline to give the amides (4) (70percent).Refluxing in toluene with sodium hydride for 12 h transfers intramolecularly the 1-aryl group of the pyridinium salt(4) to the nitrogen of the amide.Aqueous work-up cleaves (6) and the diarylamine is purified by sublimation (60percent) (overall yield ca. 30percent).