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.

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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

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article

Multicomponent Synthesis of Heteroaryl‐Annulated Spirocarbazoles

Mat­thias Zeller, Yamuna Ezhumalai, Kumaresan Prabakaran, Eswaran Dhanasekaran
Journal of Heterocyclic Chemistry
Multicomponent Synthesis of Heterocycles
article

Multicomponent Synthesis of Heteroaryl‐Annulated Spirocarbazoles

Mat­thias Zeller, Yamuna Ezhumalai, Kumaresan Prabakaran, Eswaran Dhanasekaran
article en

Abstract

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.

Journal of Heterocyclic ChemistryVol. 63(2)
Youngstown State University (US), National Central University (TW), PSG INSTITUTE OF TECHNOLOGY AND APPLIED RESEARCH (IN), Institute of Engineering (NP)
Indian Institute of Science, Indian Institute of Technology Madras
Openalex Percentile: Top 74%
Multicomponent Synthesis of Heterocycles
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Multicomponent Synthesis of Heteroaryl‐Annulated Spirocarbazoles — Mat­thias Zeller, Yamuna Ezhumalai, et al. · Journal of Heterocyclic Chemistry (2025) | TGRS Research Map | TGRS