Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds

Dianat, Shima; Mahdavi, Mohammad; Moghimi, Setareh; Mouradzadegun, Arash; Shafiee, Abbas; Foroumadi, Alireza

doi:10.1007/s11030-015-9622-2

Cited by 19 publications

(10 citation statements)

References 42 publications

(45 reference statements)

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“…B: the proposed mechanism, driven by the stability of the product and properties of the initial starting material, such as aromaticity of the ring, bulkiness of substituents and solvent. No solvent [19,60,71,79,81,83,85,90,92,93,101,105,111,112,127,133,140,147,148,161,172,192,195] 23 Water [46,76] 2 Toluene [43,49,52,70,95,109,144,145,158,159,163,164,171,186,189,190] 17 DMSO [33,36] 2 EtOH [57,84,89,104,113,115,116,<...>…”

Section: Solvents Used In the Gbb-3crmentioning

confidence: 99%

The Groebke‐Blackburn‐Bienaymé Reaction

2019

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Imidazo[1,2‐a]pyridine is a well‐known scaffold in many marketed drugs, such as Zolpidem, Minodronic acid, Miroprofen and DS‐1 and it also serves as a broadly applied pharmacophore in drug discovery. The scaffold revoked a wave of interest when Groebke, Blackburn and Bienaymé reported independently a new three component reaction resulting in compounds with the imidazo[1,2‐a]‐heterocycles as a core structure. During the course of two decades the Groebke Blackburn Bienaymé (GBB‐3CR) reaction has emerged as a very important multicomponent reaction (MCR), resulting in over a hundred patents and a great number of publications in various fields of interest. Now two compounds derived from GBB‐3CR chemistry received FDA approval. To celebrate the first 20 years of GBB‐chemistry, we present an overview of the chemistry of the GBB‐3CR, including an analysis of each of the three starting material classes, solvents and catalysts. Additionally, a list of patents and their applications and a more in‐depth summary of the biological targets that were addressed, including structural biology analysis, is given.

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Section: Solvents Used In the Gbb-3crmentioning

confidence: 99%

The Groebke‐Blackburn‐Bienaymé Reaction

2019

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“…Foroumadi and co-workers reported in 2015 the synthesis of imidazo[1,2-a]pyridine in moderate yields (82-93%) via a GBBR using NH4Cl in stoichiometric quantities and hard conditions (Scheme 1) [17]. Our methodology has some advantages, for example, the synthetic process worked well under green catalyst.…”

Section: Introductionmentioning

confidence: 85%

Microwave-Assisted Synthesis of Bis-Heterocycles Containing the Imidazo[1,2-a]Pyridine by Groebke-Blackburn-Bienaymé Reaction

Ramírez-López

Gámez-Montaño

2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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“…Alireza Foroumadi et al (in 2015) synthesized imidazo[1,2-a] pyridine or imidazo[2,1-b]thiazole bound quinolones 40 [53] via GBBR. The reaction of 2-chloro-3-formyl quinolone with 2aminoazines or 2-aminoazoles and isocyanides in the presence of NH 4 Cl catalyst in toluene solvent at reflux temperature afforded the products in 65-93 % yield (Scheme 21i).…”

Section: Gbbr Based Imcrs For the Synthesis Of Bound Type Bhcsmentioning

confidence: 99%

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Bhat

2020

ChemistrySelect

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Bis‐heterocycles (BHCs) are hybrid molecules comprising two linked, bound, spacer, or fused heterocyclic skeletons. In recent years, these compounds have attracted increased attention of scientific communities because of their improved potential applications than their discrete units. The emergence of numerous synthetic protocols utilizing Isocyanide as one of the components in multicomponent reactions has unleashed innumerable openings to design and synthesize diverse heterocyclic scaffolds and thus Isocyanide based multicomponent reactions (IMCRs) are leading today's MCR chemistry. To date, there has not been any exclusive review on the construction of BHCs via direct IMCRs or its combination with other reaction sequences in one‐pot. This article presents the first overview of IMCRs such as Ugi, Groebke‐Blackburn‐Bienaymé (GBBR), their sequential combination with other reactions, and new IMCRs established for the one‐pot synthesis of BHCs in the last two decades.

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Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds

Cited by 19 publications

References 42 publications

The Groebke‐Blackburn‐Bienaymé Reaction

The Groebke‐Blackburn‐Bienaymé Reaction

Microwave-Assisted Synthesis of Bis-Heterocycles Containing the Imidazo[1,2-a]Pyridine by Groebke-Blackburn-Bienaymé Reaction

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

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