Lanthanide One‐Dimensional Coordination Polymer Catalyzed [3+2] Annulation Reaction: Synthesis of <i>N,N’</i>‐Bicyclic Pyrazolidine Scaffolds

Abstract Self‐assembly of the multidendate ligand (H 2 L ) with lanthanide metal salts leads to the formation of one‐dimensional coordination polymers ( CP ). The structural analysis of the molecule suggests the formation of CP with ladder‐type arrangements of ligands with metal centers. The polymers CP‐1 and CP‐2 with europium and terbium were found to be anionic and coordinatively unsaturated with the existence of solvent molecules in the vacant sites. The CP s were found to be suitable catalysts for the regioselective annulation of aza‐MBH adducts with N,N , cyclic azomethine imines that lead to the formation of N,N ’‐bicyclic pyrazolidine scaffolds via [3+2] cycloaddition. The protocol tolerates a wide substrate scope with different functionalities by producing the bicyclic scaffold with better yield and excellent diastereoselectivity. The X‐ray and NMR analysis suggests the formation of cis diastereomer which is stabilized by N−H—O interaction. The synthetic utility of the pyrazolidine scaffolds is attempted for various functional group interconversions.

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Journal
Advanced Synthesis & Catalysis
Published
2025-03-11
DOI
https://doi.org/10.1002/adsc.202401300
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
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article

Lanthanide One‐Dimensional Coordination Polymer Catalyzed [3+2] Annulation Reaction: Synthesis of N,N’‐Bicyclic Pyrazolidine Scaffolds

Ramaraj Selvaraj, Govinda Rajulu G, Saravanan Subramanian, Karthikeyan Soundararajan et al.
1 links
Advanced Synthesis & Catalysis
Multicomponent Synthesis of Heterocycles
article

Lanthanide One‐Dimensional Coordination Polymer Catalyzed [3+2] Annulation Reaction: Synthesis of N,N’‐Bicyclic Pyrazolidine Scaffolds

Ramaraj Selvaraj, Govinda Rajulu G, Saravanan Subramanian, Karthikeyan Soundararajan, Sandeep Sreedharan, Rajendran Arunachalam, P.S. Subramanian, Shekhar M. S
article en

Abstract

Abstract Self‐assembly of the multidendate ligand (H 2 L ) with lanthanide metal salts leads to the formation of one‐dimensional coordination polymers ( CP ). The structural analysis of the molecule suggests the formation of CP with ladder‐type arrangements of ligands with metal centers. The polymers CP‐1 and CP‐2 with europium and terbium were found to be anionic and coordinatively unsaturated with the existence of solvent molecules in the vacant sites. The CP s were found to be suitable catalysts for the regioselective annulation of aza‐MBH adducts with N,N , cyclic azomethine imines that lead to the formation of N,N ’‐bicyclic pyrazolidine scaffolds via [3+2] cycloaddition. The protocol tolerates a wide substrate scope with different functionalities by producing the bicyclic scaffold with better yield and excellent diastereoselectivity. The X‐ray and NMR analysis suggests the formation of cis diastereomer which is stabilized by N−H—O interaction. The synthetic utility of the pyrazolidine scaffolds is attempted for various functional group interconversions.

Advanced Synthesis & CatalysisVol. 367(11)
Central Salt and Marine Chemicals Research Institute (IN), JSS Science and Technology University (IN), Anthem Biosciences (India) (IN), Council of Scientific and Industrial Research (IN), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 97%
Multicomponent Synthesis of Heterocycles
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