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  • Chem Sci Trans., 2019, 8(3),  pp 331-337  

    DOI:10.7598/cst2019.1579

    Research Article

    Synthesis of Substituted Azetidinones Derived from Dimer of Apremilast

  • YELLANKI JAGANNADHAM1,2, DODDA VIVEKANANDA REDDY2, BHOOMIREDDY RAMADEVI2 and BETHANAMUDI PRASANNA*1,2
  • 1Research Center, Department of Chemistry, Chaitanya Post Graduate College (Autonomous), Kishanpura, Hanamkonda, Warangal Telangana State-506 001, India
    2Department of Chemistry, Jawaharlal Nehru Technological University, Hyderabad, Telanagan State-500085, India
  • Abstract

    Over the past decade, design of 2-azetidinones scaffold has attracted greater interest of synthesis because of more biological and pharmacological potencies. Specifically, sulfonamide rings and their derivatives represent a medicinally and pharmaceutically important class of heterocyclic motifs that are found as the core structural skeletons in a variety of several naturally occurring alkaloids. We effectively intended 4-(3-chloro-2-oxo-4-aryllazetidin-1-yl)-2/-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethyl)-2,4`-biisoindoline-1.1`3,3-tetraones (6(a-f)). 4-Amino-2`-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-2,4`-biisoindo line-1, 1`, 3, 3`-tetraone 3 was prepared by condensation of 3-aminophthalic acid 2 with 1,3-ethoxy-4-methoxyphenyl)-2-methylsutfonylethylamine 1 by a single step. Condensation of compound 3 with various aromatic aldehydes gives substituted Schiff base of 2`-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-2,4-biisoindoline-1,1`,3,3`-tetraones (5(a-f)) which upon dehydrative annulation in the presence of chloroacetylchloride in the presence of triethylamine in DCM solvent yielded 4-(3-Chloro-2-oxo-4-aryllazetidin-1-yl)-2`-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethyl)-2,4`-biisoindoline-1.1`3,3`-tetraones 6(a-f). All the synthesized compounds were recognized by Infra Red-Vibrational spectroscopy, Proton Nuclear Magnetic Resonance, mass spectroscopy and their C, H, N analyses

    Keywords

    Biisoindoline, Azetidinones, Aminophthalic acid, Schiff base, Chloroacetyl chloride, Dehydrative annulation

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