Diversity-Oriented Synthesis of [2.2]Paracyclophane-derived Fused Imidazo[1,2-a]heterocycles by Groebke-Blackburn-Bienayme Reaction : Accessing Cyclophanyl Imidazole Ligands Library

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Stahlberger , M , Schwarz , N , Zippel , C , Hohmann , J , Nieger , M , Hassan , Z & Brase , S 2022 , ' Diversity-Oriented Synthesis of [2.2]Paracyclophane-derived Fused Imidazo[1,2-a]heterocycles by Groebke-Blackburn-Bienayme Reaction : Accessing Cyclophanyl Imidazole Ligands Library ' , Chemistry: A European Journal , vol. 28 , no. 3 , e202103511 . https://doi.org/10.1002/chem.202103511

Title: Diversity-Oriented Synthesis of [2.2]Paracyclophane-derived Fused Imidazo[1,2-a]heterocycles by Groebke-Blackburn-Bienayme Reaction : Accessing Cyclophanyl Imidazole Ligands Library
Author: Stahlberger, Mareen; Schwarz, Noah; Zippel, Christoph; Hohmann, Jens; Nieger, Martin; Hassan, Zahid; Brase, Stefan
Contributor organization: Department of Chemistry
Date: 2022-01-13
Language: eng
Number of pages: 7
Belongs to series: Chemistry: A European Journal
ISSN: 0947-6539
DOI: https://doi.org/10.1002/chem.202103511
URI: http://hdl.handle.net/10138/340569
Abstract: This report describes the synthesis of a [2.2]paracyclophane-derived annulated 3-amino-imidazole ligand library through a Groebke-Blackburn-Bienayme 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.
Subject: Fused-imidazoles
Groebke-Blackburn-Bienayme (GBB) reaction
Isocyanide Chemistry
Multicomponent reactions
[2
2]Paracyclophane
PALLADACYCLE
ISOCYANIDE
EFFICIENT
DERIVATIVES
RESOLUTION
PYRAZINES
116 Chemical sciences
Peer reviewed: Yes
Rights: cc_by_nc
Usage restriction: openAccess
Self-archived version: publishedVersion


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