Functionalization of Heterocycles by MCRs

Vicente‐García, Esther; Kielland, Nicola; Lavilla, Rodolfo

doi:10.1002/9783527678174.ch06

Cited by 7 publications

(7 citation statements)

References 135 publications

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“…Figures 2 and 3 show the 1 H and 13 C NMR spectra for the representative imidazo[1,2-a]pyridine 6a. In the 13 C NMR, the carbonyl carbon signal appears at 172.1 ppm, which confirms the formation of the GBBR product and not the formation of the oxazole by an intramolecular ring closure in the isonitrile. All of the other key signals are readily observed in these spectra.…”

Section: Resultsmentioning

confidence: 99%

“…1 H and 13 C NMR spectra were acquired on Bruker Avance III spectrometers (500 or 400 MHz). The solvent used was deuterated chloroform (CDCl3).…”

Section: General Information Instrumentation and Chemicalsmentioning

confidence: 99%

“…The internal reference for 1 H NMR spectra is trimethylsilane at 0.0 ppm. The internal reference for 13 C NMR spectra is CDCl3 at 77.0 ppm. Coupling constants are reported in Hertz (J/Hz).…”

Section: General Information Instrumentation and Chemicalsmentioning

confidence: 99%

“…In modern synthetic chemistry, there is an urgent need to design and develop new green and efficient methodologies to synthesize complex molecules from simple materials with high atom economy. The isocyanide-based multicomponent reaction (IMCR) is a powerful tool that plays a central role in the synthesis of heterocycles [13]. The GBBR is one of the most common and efficient methodologies to synthesize imidazole analogues and the method of choice to synthesize imidazo[1,2-a]pyridine-3-amines.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Imidazo[1,2-a]pyridines via Multicomponent GBBR Using α-isocyanoacetamides

Gómez

Islas‐Jácome²,

Gámez-Montaño

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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Six novel imidazo[1,2-a]pyridines were synthesized by Groebke–Blackburn–Bienaymé reactions (GBBRs) under eco-friendly conditions (10 mol% ammonium chloride catalyst in EtOH at room temperature) with moderate to good yields (76–44%) using 2-isocyano-1-morpholino-3-phenylpropan-1-one. This is the first successful use of this type of α-isocyanoacetamide in a GBBR, as these reactive isonitriles readily undergo ring-chain tautomerization, as reported in other IMCRs (isonitrile-based multicomponent reactions). The product structures contain a peptidomimetic imidazo[1,2-a]pyridine scaffold linked to an α-aminomorpholide and are of interest to medicinal chemists.

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Section: Resultsmentioning

confidence: 99%

“…1 H and 13 C NMR spectra were acquired on Bruker Avance III spectrometers (500 or 400 MHz). The solvent used was deuterated chloroform (CDCl3).…”

Section: General Information Instrumentation and Chemicalsmentioning

confidence: 99%

Section: General Information Instrumentation and Chemicalsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Imidazo[1,2-a]pyridines via Multicomponent GBBR Using α-isocyanoacetamides

Gómez

Islas‐Jácome²,

Gámez-Montaño

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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“…The efficient and novel one-pot GBBR/post-transformation strategy is a contribution in the design and development of the eco-friendly IMCR strategies 43 toward the synthesis of bis-heterocycles ( Figure 2 ), having the following advantages such as (a) it permits functionalization at the C-3 position in both heterocycles (imidazole and quinoline), (b) increases the complexity of the previously functionalized heterocycle, (c) one-pot synthesis of two different fused heterocycles, and (d) works under mild and green conditions. Thus, their application to synthesize unsymmetrical bound-type bis-heterocycles containing fused heterocycles as imidazo[2,1- b ]thiazole and 1,5-DsT with quinoline via ultrasound-assisted one-pot GBBR/S N Ar/ring-chain azido-tautomerization process under mild, catalyst- and solvent-free conditions is described here.…”

Section: Introductionmentioning

confidence: 99%

Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke–Blackburn–Bienaymé Reaction/S_NAr/Ring-Chain Azido-Tautomerization Strategy

et al. 2018

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A new, efficient, green, endogenous water-triggered, solvent- and catalyst-free ultrasound-assisted one-pot Groebke–Blackburn–Bienaymé reaction/SNAr/ring-chain azido-tautomerization strategy to synthesize bound-type fused bis-heterocycles imidazo or benzo[d]imidazo[2,1-b]thiazoles and 1,5-disubstituted tetrazole (1,5-DsT) containing quinoline moiety is described, which allows synthesis of two types of fused heterocycles in one step under mild green conditions. Antibacterial and antiamebic activities of selected newly synthesized compounds were carried out against three bacterial species: Gram-positive bacterium Staphylococcus aureus ATCC 6538 and Gram-negative bacteria Pseudomonas aeruginosa ATCC 13384 and Escherichia coli O55 and against one amebic species: Entamoeba histolytica.

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A Facile Three‐Component Catalyst‐Free Strategy: Synthesis of Indeno[1,2‐b][1,6]naphthyridine‐1,10(2H)‐dione Derivatives in Water

Zhang²,

et al. 2022

Asian J Org Chem

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A catalyst‐free protocol for synthesizing a new series of indeno[1,2‐b][1,6]naphthyridine‐1,10(2H)‐dione derivatives with good to excellent yields was established based on microwave‐assisted domino reaction of 4‐aminopyridin‐2(1H)‐ones, aldehydes and 1H‐indene‐1,3(2H)‐dione in water. The present approach exhibited useful and green features, such as water as reaction solvent, catalyst‐ and additive‐ free, short reaction time (20–30 min), as well as ease of desired products separation and purification without the need for column chromatography. Also to note, up to four new bonds were formed accompanied by generating water as sole by‐product in this one‐pot procedure.

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Functionalization of Heterocycles by MCRs

Cited by 7 publications

References 135 publications

Synthesis of Imidazo[1,2-a]pyridines via Multicomponent GBBR Using α-isocyanoacetamides

Synthesis of Imidazo[1,2-a]pyridines via Multicomponent GBBR Using α-isocyanoacetamides

Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke–Blackburn–Bienaymé Reaction/S_NAr/Ring-Chain Azido-Tautomerization Strategy

A Facile Three‐Component Catalyst‐Free Strategy: Synthesis of Indeno[1,2‐b][1,6]naphthyridine‐1,10(2H)‐dione Derivatives in Water

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Functionalization of Heterocycles by MCRs

Cited by 7 publications

References 135 publications

Synthesis of Imidazo[1,2-a]pyridines via Multicomponent GBBR Using α-isocyanoacetamides

Synthesis of Imidazo[1,2-a]pyridines via Multicomponent GBBR Using α-isocyanoacetamides

Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke–Blackburn–Bienaymé Reaction/SNAr/Ring-Chain Azido-Tautomerization Strategy

A Facile Three‐Component Catalyst‐Free Strategy: Synthesis of Indeno[1,2‐b][1,6]naphthyridine‐1,10(2H)‐dione Derivatives in Water

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Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke–Blackburn–Bienaymé Reaction/S_NAr/Ring-Chain Azido-Tautomerization Strategy