Multicomponent Synthesis of Heteroaryl‐Annulated Spirocarbazoles
ABSTRACT A series of dispirooxindole‐pyrrolidine/pyrrolizidine derivatives was synthesized in a dioxane‐methanol mixture under reflux via a 1,3‐dipolar cycloaddition reaction between an azomethine ylide and various 2‐heteroarylidene‐2,3,4,9‐tetrahydrocarbazol‐1‐ones. The structures of the resulting compounds were confirmed through spectroscopic methods (FT‐IR, 1 H‐NMR, and 13 C‐NMR) and single‐crystal x‐ray diffraction analysis. This convergent method demonstrates good generality and functional group tolerance, simplifying both traditional and modern synthetic strategies. The protocol offers advantages such as straightforward workup procedures, higher yields, shorter reaction times, and an environmentally friendly nature. X‐ray diffraction analysis also elucidated the stereochemistry and regiochemistry of the spirocyclic adducts.
Authors
- Matthias Zeller (ORCID: https://orcid.org/0000-0002-3305-852X)
- Yamuna Ezhumalai (ORCID: https://orcid.org/0000-0002-0350-6803)
- Kumaresan Prabakaran (ORCID: https://orcid.org/0000-0002-6620-1134)
- Eswaran Dhanasekaran
Institutions
- Youngstown State University (US)
- National Central University (TW)
- PSG INSTITUTE OF TECHNOLOGY AND APPLIED RESEARCH (IN)
- Institute of Engineering (NP)
Publication Details
- Journal
- Journal of Heterocyclic Chemistry
- Published
- 2025-11-14
- DOI
- https://doi.org/10.1002/jhet.70132
- Primary Topic
- Multicomponent Synthesis of Heterocycles
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Indian Institute of Science
- Indian Institute of Technology Madras