2026-10-14T03:54:20Z https://api.figshare.com/v2/oai

oai:figshare.com:article/34037275 2026-10-01T00:06:15Z category_4 category_8 category_21 category_272 category_873 category_734 category_61 category_106 category_132 portal_63 item_type_6 month_year_10_2026

Chemodivergent Synthesis of Indole Derivatives: [2 + 3]-Annulation of Oxindole-Derived MBH Carbonates with α‑Enolic Dithioesters and Subsequent Branching Transformations Yun Luo (355365) Sifeng Li (1533055) Peng Li (69518) Bin Cheng (64483) Yixuan He (4447216) Si Zhao (6639530) Ying Zhang (40767) Ping Wu (46628) Taimin Wang (3856468) Peijun Liu (563547) Biochemistry Microbiology Biotechnology Environmental Sciences not elsewhere classified Chemical Sciences not elsewhere classified Biological Sciences not elsewhere classified Developmental Biology Science Policy Infectious Diseases versatile reaction potential tailored reaction conditions subsequent branching transformations reaction proceeds via key building blocks spirooxindole derivatives spirofused chemodivergent synthetic strategy based mbh derivatives 3 ]- annulation derived mbh carbonates indole derivatives derived morita chemodivergent synthesis whereas base unique reactivity tethered indoles multisite reactivity enolic dithioesters A chemodivergent synthetic strategy for constructing a series of structurally diverse indole derivatives has been developed, utilizing oxindole-derived Morita-Baylis-Hillman (MBH) carbonates and α-enolic dithioesters as key building blocks. By leveraging the unique reactivity of both components, including the multisite reactivity of α-enolic dithioesters and the versatile reaction potential of oxindole-based MBH derivatives, the reaction proceeds via an initial [2 + 3] annulation to afford polysubstituted thiophene scaffolds tethered with an oxindole motif. This common annulation intermediate undergoes branching transformations under tailored reaction conditions: lactam-enolization-mediated trapping delivers hydrothiophene-tethered indoles, whereas base-promoted skeletal rearrangement furnishes two classes of spirooxindole derivatives spirofused with cyclopentadienes or thiopyrans. 2026-09-30T00:00:00Z Text Journal contribution 10.1021/acs.joc.6c01172.s001 https://figshare.com/articles/journal_contribution/Chemodivergent_Synthesis_of_Indole_Derivatives_2_3_-Annulation_of_Oxindole-Derived_MBH_Carbonates_with_Enolic_Dithioesters_and_Subsequent_Branching_Transformations/34037275 CC BY-NC 4.0