The first ever breakthrough toward activation of β-ketoacetanilide and subsequent C-C and C-N bond-forming intermolecular-cascade cyclization processes is demonstrated by development of the unprecedented Lewis acid property of non-toxic FeCl(3)⋅6H(2)O. Aromatic, aliphatic, α,β-unsaturated, chiral sugar-based and chromone aldehydes were regio- and stereoselectively cyclized with acetoacetanilides toward construction of valuable N-containing highly functionalized 2-pyridones (see scheme for an example).
Small Cu(0)-nanoparticles (NPs) are fabricated utilizing CuSO 4 •5H 2 O, surfactant (SDS) and ascorbic acid in aqueous medium. Its outstanding catalytic activity under low catalyst loading is developed toward reductive cleavage of isoxazoline, carbonyl azide and domino cyclization to furnish valuable 2-hydroxy-4-keto esters, primary amides and a new class of heterocycle, 4-hydroxy-2-pyrroline-5-one.Scheme 1 Fabrication of Cu(0)-NPs and their catalytic activity. † Electronic supplementary information (ESI) available: procedures, characterization data, spectra.
We demonstrate a highly regio- and stereoselective annulation strategy involving unprecedented C2-H and N-H of proline esters, α,β-unsaturated aromatic aldehydes and deactivated olefins without a catalytic aid to afford medicinally important pyrrolo[3,4-a]pyrrolizines and hexahydropyrrolizines under benign reaction conditions.
Afford Hexahydropyrrolizines. -The three--component annulation of proline esters (I) with unsaturated aldehydes (III) and maleimides or alkenes gives rise to pyrrolo[3,4-a]pyrrolizines (IV) and hexahydropyrrolizines (VI) and (VIII) in high yields. The pseudo-three-component reaction of proline esters (I) with two moles of aldehydes (III) leads to hexahydropyrrolizines (IX). -(SENGUPTA, T.; KHAMARUI, S.; SAMANTA, S.; MAITI*, D. K.; Chem. Commun. (Cambridge) 49 (2013) 85, 9962-9964, http://dx.doi.org/10.1039/c3cc45820b ; Dep. Chem., Univ. Calcutta, Kolkata 700 009, India; Eng.) -R. Staver 08-139
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