Silver(I) triflate-catalyzed protocol for the post-ugi synthesis of spiroindolines

A silver(I) triflate-catalyzed protocol for the post-Ugi synthesis of tetracyclic spiroindolines has been developed. The protocol worked best for indole-3-carbaldehyde-derived Ugi adducts obtained using anilines and 3-aryl propiolic acids. Thus, it is complementary to the previous cationic gold-catalyzed procedure that was developed for analogues Ugi substrates derived from aliphatic amines and 3-alkyl propiolic acids. Furthermore, we have demonstrated that under our new settings this domino Friedel-Crafts ipso cyclization / imine trapping process could be efficiently combined with the preceding four-component Ugi reaction into a two-step one-pot transformation

Assembly of a 1H-Pyrrol-2(5H)-one Core through a Cascade Ugi Reaction/5-endo-dig Carbocyclization/Retro-Claisen Fragmentation Process

A cascade transformation involving the Ugi reaction followed by 5-endo-dig carbocyclization and retro-Claisen fragmentation providing access to a 1H-pyrrol-2(5H)-one core is described. The operating protocol is very similar to the typical Ugi reaction settings, while the overall outcome results from the application of a 3-substituted propiolic acid and a phenylglyoxal as acid and aldehyde components, respectively. The utility of process is demonstrated through the synthesis of a small library of 5-oxo-2,5-dihydro-1H-pyrrole-2-carboxamides.status: publishe

Three-component reaction of 2-oxoaldehydes, cyclic 1,3-dicarbonyl compounds, and 4-aminopyridines

A novel three-component reaction of 2-oxoaldehydes, cyclic 1,3-dicarbonyl compounds, and 4-aminopyridines leading to the formation of zwitterionic Michael adducts is described

Ugi Reaction Followed by Intramolecular Diels-Alder Reaction and Elimination of HCl: One-Pot Approach to Arene-Fused Isoindolinones

© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim A one-pot procedure involving a four-component Ugi reaction followed by an intramolecular Diels–Alder reaction/HCl elimination cascade has been developed to provide rapid access to the isoindolinone framework in a diversity-oriented fashion. The scope of the process has been investigated with respect to all four components, and a comparison between the one-pot and sequential approaches is given. The possibility of a late-stage one-pot functionalization through Suzuki coupling has been explored.status: publishe

Heck-Suzuki tandem reaction for the synthesis of 3-benzazepines

A novel procedure for the Heck-Suzuki tandem reaction suitable for the construction of nitrogen-containing medium rings was developed to provide access toward the 3-benzazepine framework

Three-component reaction of azulene, aryl glyoxal and 1,3-dicarbonyl compound for the synthesis of various azulene derivatives

A three-component reaction of an azulene, an aryl glyoxal and a 1,3-dicarbonyl compound has been elaborated to access a series of azulene derivatives. Some of these azulene-containing adducts were further subjected to post-MCR transformations to assemble azulene–heterocycle conjugates

Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones

A series of propargylamides containing an electron-rich benzene ring was prepared through the Ugi reaction of 3,5-dimethoxyaniline with various propiolic acids, aldehydes and isocyanides. Subjecting these adducts to a gold-catalyzed intramolecular alkyne hydroarylation process allowed to efficiently construct the 2-quinolone core bearing a branched substituent on the nitrogen atom.status: publishe

Diversity-oriented synthesis of 1,3-benzodiazepines

© 2017 Elsevier Ltd A concise assembly of the 1,3-benzodiazepine core from A 3 -coupling-derived propargylamines and ortho-bromophenylisocyanates is described. The developed synthetic sequence involves the addition of propargylamine to isocyanate followed by palladium-catalyzed intramolecular alkyne hydroarylation that could be accomplished in a stepwise or one-pot manner.status: publishe