Synthesis of imidazo[1,2-a]pyridine in the presence of iodine–water catalytic system

Siddiqui, I. R.; Rai, Pragati; Rahila, .; Srivastava, Anushree; Shamim, Shayna

doi:10.1016/j.tetlet.2013.12.088

Cited by 35 publications

(9 citation statements)

References 41 publications

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“…14 However, several commercially available copper salts are very cheap and water soluble, rendering easy recovery of products. Another interesting method reported by Siddiqui et al, 15 the only metal-free A 3 -coupling of this kind, involves mild oxidant I 2 to act as a catalyst to afford imidazo[1,2- a ]pyridines at a surprisingly low temperature. However, to our dismay, we failed to obtain any desired product following their methodology for several attempts on different substrates, even under refluxing conditions.…”

Section: Introductionmentioning

confidence: 99%

Efficient and “Green” Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)–Ascorbate-Catalyzed A³-Coupling in Aqueous Micellar Media

et al. 2019

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An efficient and environmentally sustainable method for the synthesis of imidazo[1,2- a ]pyridine derivatives by domino A 3 -coupling reaction catalyzed by Cu(II)–ascorbate was developed in aqueous micellar media in the presence of sodium dodecyl sulfate (SDS). The catalyst, a dynamic combination of Cu(II)/Cu(I), was generated in situ in the reaction mixture by mixing CuSO 4 with sodium ascorbate and aided a facile 5- exo -dig cycloisomerization of alkynes with the condensation products of 2-aminopyridines and aldehydes to afford a variety of imidazo[1,2- a ]pyridines in good overall yields. A simple experimental setup, water as the “green” medium, and inexpensive catalyst and auxiliary are some of the merits of this protocol.

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Section: Introductionmentioning

confidence: 99%

Efficient and “Green” Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)–Ascorbate-Catalyzed A³-Coupling in Aqueous Micellar Media

et al. 2019

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“…Hence, further modifications of this method are based primarily on the catalysis by copper salts, such as CuHal‐Cu(OTf) 2 , [55] CuI/AgCO 3 , [56] CuI–NaHSO 4 −SiO 2 , [57] CuSO 4 /p‐TsOH, [58] CuSO 4 ⋅5H 2 O/D‐glucose/oxygen, [59] Cu(OAc) 2 [60] and copper nanoparticles [9d,61] . Besides, InBr 3 , [62] I 2 , [63] Fe 3 O 4 −KHSO 4 −SiO 2 nanoparticles [64] and Fe 3 O 4 −SiO 2 nanoparticles [65] were found to be catalytically active. A variety of electron‐withdrawing and electron‐donating substituted 2‐aminopyridines successfully participated in the reaction.…”

Section: Synthesis Of Five‐membered Nos‐heterocyclesmentioning

confidence: 99%

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

2020

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In recent years, the transition‐metal catalyzed three‐component coupling of an aldehyde, an alkyne and an amine, commonly called A3 coupling has become a powerful tool in organic synthesis. The aim of this review is to give a general overview of A3 coupling utility in the synthesis of heterocycles, highlighting the variety of compounds that can be directly accessed from single reactions. The diverse A3 coupling based methodologies that have been developed for the synthesis of N,O,S‐heterocycles are presented, emphasizing the influence of the reaction conditions and the use of additional reagents in the outcome of the transformations.

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“…Several applications of these reactions can be found in the literature. For example, they have been used to prepare nitrogen-enriched heterocyclic scaffolds, imidazo[1,2- a ]pyridines, dihydropyrroles, substituted 1 H -chromeno[2,3- d ]pyrimidine-5-carboxamides, imidazoles, amino acids, 1,4-benzodiazepine-2,5-diones, and N-substituted diketopiperazines, just to mention a few. It is clear that in the majority of the examples reported, aldehydes play a crucial role, and therefore, it is of paramount importance to be able to prepare the aldehyde component for the specific sought after application.…”

Section: Introductionmentioning

confidence: 99%

FormylBODIPYs: Privileged Building Blocks for Multicomponent Reactions. The Case of the Passerini Reaction

et al. 2016

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Eleven formyl-containing BODIPY dyes were prepared by means of either the Liebeskind-Srogl cross-coupling reaction or the Vilsmeier reaction. These dyes were used as components in the Passerini reaction to give highly substituted BODIPY dyes. A joined spectroscopic and theoretical characterization of the synthesized compounds was conducted to unravel the impact of the structural rigidity/flexibility on the photophysical signatures. These dyes were tested as fluorescent trackers for phagocytosis. Additionally, they proved to be useful to stain different blood cells with an intense and stable signal at a very low exposure time.

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Synthesis of imidazo[1,2-a]pyridine in the presence of iodine–water catalytic system

Cited by 35 publications

References 41 publications

Efficient and “Green” Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)–Ascorbate-Catalyzed A³-Coupling in Aqueous Micellar Media

Efficient and “Green” Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)–Ascorbate-Catalyzed A³-Coupling in Aqueous Micellar Media

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

FormylBODIPYs: Privileged Building Blocks for Multicomponent Reactions. The Case of the Passerini Reaction

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Synthesis of imidazo[1,2-a]pyridine in the presence of iodine–water catalytic system

Cited by 35 publications

References 41 publications

Efficient and “Green” Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)–Ascorbate-Catalyzed A3-Coupling in Aqueous Micellar Media

Efficient and “Green” Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)–Ascorbate-Catalyzed A3-Coupling in Aqueous Micellar Media

A3 Coupling Reaction in the Synthesis of Heterocyclic Compounds

FormylBODIPYs: Privileged Building Blocks for Multicomponent Reactions. The Case of the Passerini Reaction

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Product

Resources

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Efficient and “Green” Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)–Ascorbate-Catalyzed A³-Coupling in Aqueous Micellar Media

Efficient and “Green” Synthetic Route to Imidazo[1,2-a]pyridine by Cu(II)–Ascorbate-Catalyzed A³-Coupling in Aqueous Micellar Media

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds