Cascade Synthesis of 2-Azafluorene, Azocine, and Azabicyclononane Derivatives by Reaction of Activated Acetylenes with Some β-Amino Ketones

Metal-free syntheses of new azocinesviaaddition reactions of enaminones with acenaphthoquinone followed by oxidative cleavages of the corresponding vicinal diols

“…Ten aromatic hydrogens were also indicated by the presence of three doublets (d ¼ 7.14, 3 J ¼ 8.5 Hz), (d ¼ 7.41, 3 J ¼ 8.5 Hz), and (d ¼ 7.91, 3 J ¼ 6.9 Hz), and one triplet (d ¼ 8.18, 3 J ¼ 8.6 Hz) along with a multiplet at d ¼ 7.57-7.80 ppm. The 1 Hdecoupled 13 C-NMR spectrum of 3b showed 24 distinct signals in agreement with the proposed structure. The high-resolution mass spectrum of 3b displayed an [M + H] + peak at m/z ¼ 426.1700, in agreement with the proposed structure.…”

“…The molecular structures of all products 3a-t were also elucidated from their IR, 1 H-NMR, 13 C-NMR and HRMS spectra. Finally, the structure of product 3c was determined unambiguously from an X-ray diffraction study (Fig.…”

“…Scheme 1 Procedure for one-pot syntheses of azocines 3a-t pathway for azocine derivative synthesis, with this pathway involving the reaction of an activated acetylene with a b-amino ketone. 13 Most of the methods developed for azocine synthesis use expensive and inaccessible raw materials. In addition, some of the problems associated with the previous methods include the employment of metals as catalysts, harsh reaction conditions, poor product efficiency and tedious work-up.…”

Efficient synthesis of β‐aminoketones catalyzed by Fe3O4@ quillaja sapogenin/Ni (II) as a novel magnetic nano‐catalyst

“…Compounds of the β-aminoketones, which are necessary intermediates in herbal products, were provided through the mentioned process. [17,20] Previously, a portion of the β-aminoketone's compounds had already been catalyzed by H 3 PW 12 O 30 (hetero poly acids), [21] carbon-based solid acid, [22] diaryliodonium (III), [23] BiNO 3 , [24] citric acid, [25] proline and solution, [26,27] calixarenes, [28] Cu/NH 2 -SBA-15,, [29] InCl 3 [30] ionic liquid (carboxyl-functionalized poly) (CFPIL). [31] The mentioned catalysts for this purpose, despite having some advantages, have also some disadvantages, including time consuming reaction process, a small yield of products, harmfulness, and low efficiency in the recovery process.…”