Toward versatile methods leading to highly functionalized imidazo[1,2-a]pyridines

N N cyclocondensations oxidative cyclizations multicomponent reactions rearrangements tandem processes C-H activations/functionalizationsAbstract Advances in the last decade for the synthesis of the imidazo[1,2-a]pyridine scaffold from various substrates employing approaches such as multicomponent reactions, tandem processes, rearrangement reactions, inter-and intramolecular oxidative/reductive cyclizations, and transition-metal-catalyzed C-H activation are summarized in this review. The mechanisms for the selected transformations are also discussed. 1

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“…As an application of this protocol, a tricyclic imidazo[1,2-a]pyridine containing an azepine analogue was synthesized by a concise route. 94…”

Section: Review Syn Thesis Scheme 35mentioning

confidence: 99%

Recent Developments in the Synthesis of Imidazo[1,2-a]pyridines

Pericherla¹,

Kaswan²,

Pandey³

et al. 2015

Synthesis

187

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“…In 2012, Schmitt et al reported a cascade synthesis of 3-aroylimidazo[1,2-a]pyridines from N-acylamidine with thionyl chloride followed by a reaction with phenacyl bromide in DMF (Scheme 1B, route b). 15 Recently, He's group developed intramolecular oxidative α-amination of carbonyl compounds by I 2 /H 2 O 2 to give 3aroylimidazo[1,2-a]pyridines (Scheme 1B, route c). 16 Similarly, Wen et al demonstrated copper-catalyzed intramolecular oxidative amination of enaminones for the synthesis of 3aroylimidazo[1,2-a]pyridines (Scheme 1B, route d).…”

Section: ■ Introductionmentioning

confidence: 99%

“…It can be prepared directly from aminooxygenation of 2-aminopyridines with 3-arylpropiolaldehydes catalyzed by Fe, Au/Ag, Cu, or NIS (Scheme B, route a). In 2012, Schmitt et al reported a cascade synthesis of 3-aroylimidazo[1,2- a ]pyridines from N -acylamidine with thionyl chloride followed by a reaction with phenacyl bromide in DMF (Scheme B, route b) . Recently, He’s group developed intramolecular oxidative α-amination of carbonyl compounds by I 2 /H 2 O 2 to give 3-aroylimidazo[1,2- a ]pyridines (Scheme B, route c) .…”

Section: Introductionmentioning

confidence: 99%

I₂-Catalyzed Three-Component Consecutive Reaction for the Synthesis of 3-Aroylimidazo[1,2-a]-N-Heterocycles

et al. 2021

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A convenient one-pot, three-component reaction has been developed for the synthesis of 3-aroylimidazo[1,2-a]-N-heterocycles from aryl ketones and 2-amino-N-heterocycles using dimethyl sulfoxide as a methylene donor. The reaction proceeds smoothly catalyzed by I2 in the presence of K2S2O8 and affords the desired products in moderate to good yields. This protocol offers significant superiority in accessing biologically active 3-aroylimidazo[1,2-a]-N-heterocycles with various substitution patterns.

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“…The most generally applied methods for the synthesis of pharmaceutical imidazo[1,2‐ a ]pyridines are based on the reactions of 2‐aminopyridines with bromoaldehydes or bromoketones. [5,9a,9c,13a,14] New methods leading to functionalized imidazo[1,2‐ a ]pyridines through N ‐(pyridin‐2‐yl)amidines have been recently reported 15a,15b. Multi‐component reactions16 of 2‐aminopyridine with aldehydes and isocyanides, nitrile, thiocyanates, imidazoline‐2,4,5‐trione or acetylene, cascade synthesis,17 and palladium catalyzed C–C bond cross‐coupling reactions18 are very promising for the preparation of imidazo[1,2‐ a ]pyridine derivatives.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Synthesis of N‐(Imidazo[1,2‐a]pyridin‐3‐yl)‐ and N‐(Imidazo[2,1‐b][1,3]thiazol‐5‐yl)sulfonamides

et al. 2012

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The reaction of 2-aminopyridines or 2-aminothiazole with N-(2,2-dichloro-2-phenylethylidene)arensulfonamides affords the corresponding products of nucleophilic addition to the azomethine group, N-[2,2-dichloro-2-phenyl-1-(heterylamino)ethyl]sulfonamides, in good yields. The latter are easily cyclized to (imidazo[1,2-a]pyridin-3-yl)sulfonamides and (imidazo[2,1-b]thiazol-5-yl)sulfonamides in the presence of [a] A.E. 369 Scheme 4. A tentative route for the formation of imidazo[1,2-a]pyridines 5.www.eurjoc.org

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Toward versatile methods leading to highly functionalized imidazo[1,2-a]pyridines

Cited by 12 publications

References 31 publications

Recent Developments in the Synthesis of Imidazo[1,2-a]pyridines

Recent Developments in the Synthesis of Imidazo[1,2-a]pyridines

I₂-Catalyzed Three-Component Consecutive Reaction for the Synthesis of 3-Aroylimidazo[1,2-a]-N-Heterocycles

One‐Pot Synthesis of N‐(Imidazo[1,2‐a]pyridin‐3‐yl)‐ and N‐(Imidazo[2,1‐b][1,3]thiazol‐5‐yl)sulfonamides

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Toward versatile methods leading to highly functionalized imidazo[1,2-a]pyridines

Cited by 12 publications

References 31 publications

Recent Developments in the Synthesis of Imidazo[1,2-a]pyridines

Recent Developments in the Synthesis of Imidazo[1,2-a]pyridines

I2-Catalyzed Three-Component Consecutive Reaction for the Synthesis of 3-Aroylimidazo[1,2-a]-N-Heterocycles

One‐Pot Synthesis of N‐(Imidazo[1,2‐a]pyridin‐3‐yl)‐ and N‐(Imidazo[2,1‐b][1,3]thiazol‐5‐yl)sulfonamides

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I₂-Catalyzed Three-Component Consecutive Reaction for the Synthesis of 3-Aroylimidazo[1,2-a]-N-Heterocycles