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  • 42 Reads
Alternative and Complementary Approaches to the Asymmetric Synthesis of 3-Aryl or Alkyl Substituted NH Free Isoindolinones
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Alternative and complementary synthetic approaches to the asymmetric synthesis of poly and diversely substituted isoindolinones alkylated or arylated at C-3 have been developed. They mainly differ from the creation of the stereogenic center embedded in the benzolactam nucleus which can be inserted in the models at early or later stage as well in the synthetic process.
  • Open access
  • 24 Reads
Asymmetric Synthesis of (+)-Coniine,(-)-Coniceine, (+)-b-Conhydrine,(+)-Sedamine and(+)-Allosedamine by a Strategic Combination of RCM with Nucleophilic 1,2-Addition on SAMP-Hydrazones
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A tactically new approach to the asymmetric synthesis of the piperidine alkaloids (+)-coniine, (-)-coniceine, (+)-b -conhydrine, (+)-sedamine and (+)-allosedamine has been developed. The key step is the elaboration of the piperidine template equipped with suitably functionalized appendages at the stereodefined C-2 position. Subsequent manipulation of the appropriate functionalities gave rise to the targeted compounds in high yields and high level of enantioselectivity.
  • Open access
  • 61 Reads
Catalytic Synthesis of Ethyl ß-arylamino Crotonates and 2-methyl-4-quinolone using Preyssler Heteropolyacid, H14[NaP5W30O110] and its supported as Catalysts
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A variety of aromatic anilines react with methyl acetoacetate in the presence of catalytic amount of Preyssler’s and molybdenum substituted Preyssler heteropolyacid, H14[NaP5W30O110], H14[NaP5W29MoO110] and silica supported Preyssler, H14[NaP5W30O110]/SiO2, to afford the corresponding ethyl ß-arylamino crotonates, in excellent yields. The catalyst can be recovered and reused. Synthesis of 4-quinolones from the cyclization of ethyl ß-arylamino crotonates in the presence of diphenyl ether under reflux conditions is reported.
  • Open access
  • 57 Reads
Syntheses of 8,9,10,11-Tetrahydro-pyrido[3,2,1-jk]carbazoles, 1,2,3, 11b-Tetrahydro-pyrido[3,2,1-jk]carbazoles and 7a,8,9,10,11,11a-Hexahydro-pyrido[3,2,1-jk]carbazoles
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Pyrido[3,2,1-jk]carbazol-6-one in its partial hydrogenated form is part of the heterocyclic skeleton of many natural products (e. g. strychnos alkaloids such as strychninolones and brucinolones, picrasidin Q and olivacin alkaloids). It possesses the biological interesting combination of an indole structure and of a 2-quinolone; Comparison with strychnos alkaloids shows that it has already four rings and two oxygen functions in the correct position.
  • Open access
  • 45 Reads
Aza-Diels-Alder versus 1,3-Dipolar Cycloadditions of Methyl Glyoxylate Oxime with Cyclopentadiene
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The acid-catalyzed [3+2] and [4+2] cycloadditions between methyl glyoxylate oxime (1) and cyclopentadiene were investigated using various Lewis and/or Bronsted acids at different temperatures in dichloromethane as solvent. Besides the expected new adducts, (±)-methyl [(3-exo)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylate (2) and (±)-methyl [(3-endo)-2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylate (3) a third addict, (±) methyl (1R,4R,5R)-(2-ox-3-azabicyclo[3.3.0]oct-7-ene)-4-carboxylate (4), whose formation can be explained by a concerted 1,3-dipolar cycloaddition, was obtained. Yields and product ratios were found to be more dependent on the catalyst than on the temperature; these results and the stereochemistry of the adducts, confirmed by spectroscopic data (1H and 13C NMR) and by X-ray cycloadditions.
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