Modular Synthesis of Di- and Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors

Toledo, Ian de; Grigolo, Thiago A.; Bennett, James M.; Elkins, J.M.; Pilli, Ronaldo A.

doi:10.1021/acs.joc.9b01844

Cited by 18 publications

(7 citation statements)

References 41 publications

(120 reference statements)

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“…Toledo and co-workers recently reported that imidazoles 131 could also be synthesized by a metal-free, one-pot process from ketones 129 via oxidation and subsequent dehydrative coupling with aldehydes and ammonium acetate (Scheme 26). 51 This method had a reasonable level of functional group tolerance including basic pyridines and cyclopropanes.…”

Section: Review Organic and Biomolecular Chemistrymentioning

confidence: 99%

Recent advances in the synthesis of imidazoles

Shabalin

Camp

2020

Org. Biomol. Chem.

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Section: Review Organic and Biomolecular Chemistrymentioning

confidence: 99%

Recent advances in the synthesis of imidazoles

Shabalin

Camp

2020

Org. Biomol. Chem.

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“…Another synthetic strategy used to construct disubstituted imidazole derivatives 27 from methyl ketones 28 consisted of exploiting its metal-free acid-catalyzed oxidation and coupling with aldehydes 29 and 30 in the presence of ammonium acetate ( Figure 14 ) [ 25 ].…”

Section: Synthesis and Functionalization Of Imidazolementioning

confidence: 99%

Imidazole: Synthesis, Functionalization and Physicochemical Properties of a Privileged Structure in Medicinal Chemistry

Tolomeu

Fraga

2023

Molecules

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Imidazole was first synthesized by Heinrich Debus in 1858 and was obtained by the reaction of glyoxal and formaldehyde in ammonia, initially called glyoxaline. The current literature provides much information about the synthesis, functionalization, physicochemical characteristics and biological role of imidazole. Imidazole is a structure that, despite being small, has a unique chemical complexity. It is a nucleus that is very practical and versatile in its construction/functionalization and can be considered a rich source of chemical diversity. Imidazole acts in extremely important processes for the maintenance of living organisms, such as catalysis in enzymatic processes. Imidazole-based compounds with antibacterial, anti-inflammatory, antidiabetic, antiparasitic, antituberculosis, antifungal, antioxidant, antitumor, antimalarial, anticancer, antidepressant and many others make up the therapeutic arsenal and new bioactive compounds proposed in the most diverse works. The interest and importance of imidazole-containing analogs in the field of medicinal chemistry is remarkable, and the understanding from the development of the first blockbuster drug cimetidine explores all the chemical and biological concepts of imidazole in the context of research and development of new drugs.

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“…Pilli et al in 2019 reported a one-pot, modular approach for the synthesis of 2,4(5)-disubstituted imidazoles based on ketone oxidation, followed by imidazole condensation with aldehydes. They extended this methodology to the synthesis of trisubstituted imidazoles using this oxidation-condensation protocol, followed by bromination and Suzuki coupling [10] (Scheme 1c).…”

Section: Introductionmentioning

confidence: 99%

N‐Heterocyclic Carbene‐Catalyzed Condensation/ Oxidation/ Cyclization/ Aromatization Cascade for the Synthesis of Tri‐ and Tetra‐Substituted Imidazoles

2023

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In this study, a novel and efficient one‐pot tandem synthesis of 2,4,5‐tri‐ and 1,2,4,5‐tetra‐substituted imidazoles is described. In the first step of the sequence, benzil is formed via benzoin condensation catalyzed by N‐heterocyclic carbene, followed by in situ aerobic oxidation. Next, it is reacted with another aldehyde and ammonium acetate (or amine) to produce the polysubstituted imidazole. The reaction proceeds smoothly in high yield and short reaction time in ethanol as a green solvent. The current strategy shows high functional group tolerance with respect to aldehydes and avoids the need for ligands and reducing agents. This method allows the synthesis of complex molecules in a one‐pot procedure without isolating intermediates.

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Modular Synthesis of Di- and Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors

Cited by 18 publications

References 41 publications

Recent advances in the synthesis of imidazoles

Recent advances in the synthesis of imidazoles

Imidazole: Synthesis, Functionalization and Physicochemical Properties of a Privileged Structure in Medicinal Chemistry

N‐Heterocyclic Carbene‐Catalyzed Condensation/ Oxidation/ Cyclization/ Aromatization Cascade for the Synthesis of Tri‐ and Tetra‐Substituted Imidazoles

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