K<sub>2</sub>CO<sub>3</sub>-Generated Azomethine Ylides and Highly Regioselective (3 + 2)-Cycloaddition to Functionalized Dihydropyrrolizines: A DFT-Supported Mechanism
The K<sub>2</sub>CO<sub>3</sub>-mediated synthesis of frequently used azomethine ylide intermediates and their highly regioselective 1,3-dipolar cycloaddition reactions are elegantly demonstrated, offering a regiocontrolled synthesis of valuable fused N-heterocycles. These relatively stable azomethine ylides undergo dual C-C and C-N coupled cyclization with terminal alkynes and N-substituted maleimides under metal-free conditions, providing a concise and aesthetically pleasing route to functionalized 2,3-dihydro-1<i>H</i>-pyrrolizines. The detection of intermediates and density functional theory (DFT) calculations confirm the regio- and stereoselectivity of this cycloaddition process, highlighting its precision and efficiency.
Authors
- Dilip K. Maiti (ORCID: https://orcid.org/0000-0001-8743-2620)
- Shobhon Aich
- Saikat Khamarui (ORCID: https://orcid.org/0000-0001-6785-0227)
- Sabir A. Molla
- Narendra Nath Ghosh (ORCID: https://orcid.org/0000-0001-6026-4639)
- Debasish Ghosh (ORCID: https://orcid.org/0000-0001-7162-613X)
Institutions
- University of Calcutta (IN)
- Government Medical College (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-09-26
- DOI
- https://doi.org/10.1021/acs.joc.5c00367
- Citations
- 1
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94