Diversity‐Oriented Synthesis of Paracyclophane‐derived Fused Imidazoheterocycles by Groebke‐Blackburn‐Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library

This report describes the synthesis of a [2.2]paracyclophane‐derived annulated 3‐amino‐imidazole ligand library through a Groebke‐Blackburn‐Bienaymé three‐component reaction (GBB‐3CR) approach employing formyl‐cyclophanes in combination with diverse aliphatic and aromatic isocyanides and heteroaroma...

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Published inChemistry : a European journal Vol. 28; no. 3
Main Authors Stahlberger, Mareen, Schwarz, Noah, Zippel, Christoph, Hohmann, Jens, Nieger, Martin, Hassan, Zahid, Bräse, Stefan
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.01.2022
Subjects
Chemistry
Crystallography
Imidazole
Libraries
Ligands
Pyrazines
Pyridines
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Summary:This report describes the synthesis of a [2.2]paracyclophane‐derived annulated 3‐amino‐imidazole ligand library through a Groebke‐Blackburn‐Bienaymé three‐component reaction (GBB‐3CR) approach employing formyl‐cyclophanes in combination with diverse aliphatic and aromatic isocyanides and heteroaromatic amidines. The GBB‐3CR process gives access to skeletally‐diverse cyclophanyl imidazole ligands, namely 3‐amino‐imidazo[1,2‐a]pyridines and imidazo[1,2‐a]pyrazines. Additionally, a one‐pot protocol for the GBB‐3CR by an in situ generation of cyclophanyl isocyanide is demonstrated. The products were analyzed by detailed spectroscopic techniques, and the cyclophanyl imidazo[1,2‐a]pyridine was confirmed unambiguously by single‐crystal X‐Ray crystallography. The cyclophanyl imidazole ligands can be readily transformed to showcase their useful utility in preparing N,C‐palladacycles through regioselective ortho‐palladation.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202103511