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March 7, 2026Asian Journal of Organic Chemistry0 citations

Exploring the Bifunctional Nature of L ‐Proline for the Organocatalytic Synthesis of 2‐Amino‐1,3,4‐thiadiazoles and 2‐Amino‐1,3,4‐oxadiazoles Under Mild Reaction Conditions

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RSRajeev SinghNANaseem Ahmed

Key Points

  • The aim is to explore the use of L-proline as an organocatalyst for synthesizing thiadiazoles and oxadiazoles.
  • Conducted one-pot synthesis using benzothioamide and phenylformamide.
  • Utilized L-proline as a naturally occurring organocatalyst.
  • Employed isopropanol as a green solvent under metal-free conditions.
  • Analyzed the mechanistic role of L-proline in facilitating reactions.
  • Achieved moderate to high yields of 70%-92% for the target compounds.
  • Demonstrated effective formation of iminium transition states.
  • Established intermolecular hydrogen bonding was crucial for reaction efficiency.

Abstract

ABSTRACT We demonstrate a simple and efficient one‐pot synthesis of 2‐amino‐1,3,4‐thiadiazoles and 2‐amino‐1,3,4‐oxadiazoles by integrating benzothioamide with phenylformamide and using L ‐proline as a naturally occurring organocatalyst. A wide range of substrates was successfully synthesized with moderate to high yields (70%–92%) by using isopropanol as a green solvent under metal‐free ambient conditions. The mechanistic insights capitalize on the bifunctional nature of L ‐proline, enabling the formation of the iminium transition state and intermolecular hydrogen bonding.

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Cite This Study

Singh et al. (2026) studied this question.

synapsesocial.com/papers/69abc1d75af8044f7a4ead0ahttps://doi.org/10.1002/ajoc.70340
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