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Abstract <p>The first use of a pyrrolidinium-based Brønsted acidic ionic liquid, 1-methyl-1-sulfopyrrolidinium chloride (<b>MSP-Cl</b>), as a highly efficient catalyst for the synthesis of thiosemicarbazones is reported. The catalyst was prepared in a single step from <i>N</i>-methylpyrrolidine and chlorosulfonic acid in toluene and fully characterized by NMR, IR, and ESI-MS. At a loading of 0.04 mol %, it promoted the condensation of various alde­hydes with thiosemicarbazides under mild conditions (25–35°C) to afford the corresponding thiosemi­carbazones in 94–97% yields within 90 min. Compared with reported systems, <b>MSP-Cl</b> offered shorter reaction times, higher yields, and cleaner reactions under ambient conditions. The process is metal-free, operationally simple, and environmentally benign. A plausible ionic activation mechanism is proposed.</p>

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1-Methyl-1-sulfopyrrolidinium Chloride as an Efficient Catalyst for the Synthesis of Biologically Active Thiosemicarbazone Derivatives

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • D. Shejul,
  • B. Shelke,
  • M. Shivoorkar,
  • D. Wagare,
  • U. Patil,
  • P. Deshpande,
  • D. Lingampalle

摘要

Abstract

The first use of a pyrrolidinium-based Brønsted acidic ionic liquid, 1-methyl-1-sulfopyrrolidinium chloride (MSP-Cl), as a highly efficient catalyst for the synthesis of thiosemicarbazones is reported. The catalyst was prepared in a single step from N-methylpyrrolidine and chlorosulfonic acid in toluene and fully characterized by NMR, IR, and ESI-MS. At a loading of 0.04 mol %, it promoted the condensation of various alde­hydes with thiosemicarbazides under mild conditions (25–35°C) to afford the corresponding thiosemi­carbazones in 94–97% yields within 90 min. Compared with reported systems, MSP-Cl offered shorter reaction times, higher yields, and cleaner reactions under ambient conditions. The process is metal-free, operationally simple, and environmentally benign. A plausible ionic activation mechanism is proposed.