Diversity‐Oriented Synthesis of [2.2]Paracyclophane‐derived Fused Imidazo[1,2‐<i>a</i>]heterocycles by Groebke‐Blackburn‐Bienaymé Reaction: Accessing Cyclophanyl Imidazole Ligands Library

Stahlberger, Mareen; Schwarz, Noah; Hassan, Zahid; Zippel, Christoph; Hohmann, Jens; Nieger, Martin; Bräse, Stefan

doi:10.1002/chem.202103511

Cited by 7 publications

(1 citation statement)

References 47 publications

(12 reference statements)

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“…Although most authors work directly with isocyanide, several methodologies that avoid isolating the unstable isocyanide intermediate have recently been reported. Thus, using I 2 -PPh 3 -Et 3 N reagent [ 79 ], and triphosgene, Et 3 N [ 80 ], isocyanide is synthesized in situ from N -formamide 155 ( Scheme 32 ).…”

Section: Synthesis Of Heterocycles Using 13-diaza-13-butadienesmentioning

confidence: 99%

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

et al. 2022

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Many heterocyclic compounds can be synthetized using diaza-1,3-butadienes (DADs) as key structural precursors. Isolated and in situ diaza-1,3-butadienes, produced from their respective precursors (typically imines and hydrazones) under a variety of conditions, can both react with a wide range of substrates in many kinds of reactions. Most of these reactions discussed here include nucleophilic additions, Michael-type reactions, cycloadditions, Diels–Alder, inverse electron demand Diels–Alder, and aza-Diels–Alder reactions. This review focuses on the reports during the last 10 years employing 1,2-diaza-, 1,3-diaza-, 2,3-diaza-, and 1,4-diaza-1,3-butadienes as intermediates to synthesize heterocycles such as indole, pyrazole, 1,2,3-triazole, imidazoline, pyrimidinone, pyrazoline, -lactam, and imidazolidine, among others. Fused heterocycles, such as quinazoline, isoquinoline, and dihydroquinoxaline derivatives, are also included in the review.

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Section: Synthesis Of Heterocycles Using 13-diaza-13-butadienesmentioning

confidence: 99%

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

et al. 2022

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Synthesis of Fused Imidazoles and Pyrimidinones from 2‐Aminoazines

Wang,

Jiang,

Liu

et al. 2024

Asian J Org Chem

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Fused imidazole and pyrimidine heterocycles represent two important classes of organic compounds. Numerous synthetic methods have been developed for the synthesis of these compounds due to their diverse biological activities and potential pharmaceutical applications. This review provides a comprehensive assessment of the cutting‐edge methods used in the synthesis of fused heterocycles from pyridin‐2‐amines and their aza derivatives involving reaction with 1,3‐dicarbonyl compounds or α‐halo carbonyl compounds. In addition, the Groebke‐Blackburn‐Bienaymé (GBB) reaction, metal‐mediated reactions and other related reaction systems have been considered. We summarize the pertinent literature on related synthetic methods in the period 2020 to 2023. The analysis provided can inform future developments directed at new cost‐effective approaches to the synthesis of fused imidazole and fused pyrimidine analogues.

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

Stahlberger

Schwarz

Hassan

et al. 2021

Chemistry A European J

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This report describes the synthesis of a [2.2]paracyclophane-derived annulated 3-amino-imidazole ligand library through a Groebke-Blackburn-Bienaymé threecomponent reaction (GBB-3CR) approach employing formylcyclophanes 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 [a

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

Cited by 7 publications

References 47 publications

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

Synthesis of Fused Imidazoles and Pyrimidinones from 2‐Aminoazines

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

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