JOURNAL ARTICLE

Ring‐Rearrangement Driven Formal (3 + 2) Cycloaddition of Enaminone‐Based Thioalkynes with Nitriles to Form Thiazole Containing Bis‐Heterocycles.

  • Published In: European Journal of Organic Chemistry, 2025, v. 28, n. 31. P. 1 1 of 3

  • Database: Academic Search Ultimate 2 of 3

  • Authored By: Rankan, Chandran; Sharma, Abha; Tiwari, Keshri Nath 3 of 3

Abstract

Herein, a one‐pot synthesis of 3,4‐dihydropyridin‐2(H)‐one containing thiazole derivatives is reported by Bronsted acid‐mediated ring‐rearrangement and formal (3 + 2) cycloaddition reaction of enaminone‐based thioalkyne with alkyl/aryl nitrile. The developed protocol demonstrates a wide substrate scope for both the reacting partners with high atom‐economy furnishing very high to excellent yields of pharmaceutically relevant bis‐heterocyclic derivatives. Based on outcome of the product and control experiments, a plausible reaction mechanism has also been proposed. The gram‐scale synthesis and further synthetic transformation demonstrate the synthetic efficacy and utility of the developed protocol. [ABSTRACT FROM AUTHOR]

Additional Information

  • Source:European Journal of Organic Chemistry. 2025/08, Vol. 28, Issue 31, p1
  • Document Type:Article
  • Subject Area:Chemistry
  • Publication Date:2025
  • ISSN:1434-193X
  • DOI:10.1002/ejoc.202500287
  • Accession Number:187572583
  • Copyright Statement:Copyright of European Journal of Organic Chemistry is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

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