Solvent-free synthesis of 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling of phenols with cinnamic acid catalyzed by molecular iodine

Kamat, Durga P.; Tilve, Santosh G.; Kamat, Vijayendra P.

doi:10.1016/j.tetlet.2012.06.069

Cited by 20 publications

(4 citation statements)

References 24 publications

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“…Iodine has high tolerance to moisture as well as air making it ideal catalyst. It can be easily removed from the reaction mixture by washing with reducing agents 27 . The use of iodine as a catalyst is not only the cost effective and environmentally benign, but also experimentally simple, easy to handle, clean, efficient and safe 28 .…”

Section: Introductionmentioning

confidence: 99%

Iodine-catalyzed three component reaction: a novel synthesis of 2-aryl-imidazo[1,2-a]pyridine scaffolds

Puttaraju

Shivashankar

2013

RSC Adv.

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A facile and efficient protocol for the synthesis of novel imidazo[1,2-a]pyridines has been developed by one-pot reaction of aromatic aldehydes with 2-amino-5-chloropyridine and tertbutylisocyanide in the presence of I 2 in toluene at 70 °C . The present approach offers the advantages of simple methodology, clean, high atom-economy, mild condition, short reaction time, wide substrate scope, low environmental impact and high yield. Key WordsIodine, Imidazopyridines, Imidazo[1,2-a]pyridine, 2-aminopyridine, tert-butylisocyanide. IntroductionMulti-component synthesis have received considerable attention of organic chemists and emerged as a powerful tool for the construction of novel and complex molecular structures due to their advantages over conventional multistep synthesis. The major advantages of MCR's include low cost, shorter reaction times, high atom economy, energy saving and avoidance of time consuming and expensive protection, deprotection, isolation and purification process Result and discussionFirst the optimization of the reaction was studied for which the reaction of 2-chloropyridine-3-carbaldehyde, 5-chloro-pyridin-2-ylamine and tert-butylisocyanide was selected as a The role of solvents on the synthesis of imidazo[1,2-a]pyridine was then studied and the results are depicted (Table 2). Replacing the ethanol by chloroform produced the model in an A probable mechanistic pathway for the formation of imidazo[1,2-a]pyridine is outlined, ConclusionIn conclusion, a straightforward and efficient protocol for the one pot synthesis of Exprimental General informationThe melting points were determined by open capillary method using electric melting point apparatus and are uncorrected. The IR spectra (KBr disc) were recorded on a Shimadzu-8400SFT-IR Spectrophotometer.1 H NMR spectra were recorded on Bruker 300 MHz spectrometer and solution. The organic layer was separated and aqueous layer was extracted with ethyl acetate (15 ml X 3). The combined organic phase were washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude product which was purified on silica gel using hexane and ethyl acetate (7:3). 56.9, 104.5, 110.8, 117.3, 120.7, 121.3, 121.8, 123.2, 124.5, 126.0, 127.0, 128.6, 154.5 55.9, 117.8, 120.5, 121.7, 122.7, 125.7, 126.4, 131.1, 136.6, 140.7, 148.8, 149 3, 30.5, 56.8, 117.3, 119.9, 121.4, 122.8, 125.3, 125.6, 126.5, 132.3, 140.0, 140 C, 60.08: H, 5.67: N, 13.14: S, 10.02. Found: C, 59.91: H, 5.54: N, 13.01: S, 9.97. 0, 56.7, 109.8, 113.3, 117.5, 120.0, 120.7, 121.6, 124.7, 126.0, 130.8, 140.6, 151.8 56.7, 109.8, 113.3, 117.5, 120.0, 120.7, 121.6, 124.7, 126.0, 130.8, 140.6, 151.8 55, 57.31, 105.08, 114.07, 114.11, 117.26, 117.92, 121.14, 131.17, 140.89, 140.93, 145.86, 149.71, 150.56, 152.50 N-tert-butyl-6-chloro-2-(1H-imidazol-4-yl)H-imidazo[1,2-a]pyridin-3-amine (2g)

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Section: Introductionmentioning

confidence: 99%

Iodine-catalyzed three component reaction: a novel synthesis of 2-aryl-imidazo[1,2-a]pyridine scaffolds

Puttaraju

Shivashankar

2013

RSC Adv.

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“…11 The 3,4-dihydrocoumarin system is widely distributed in nature, and some derivatives have been shown to exhibit pharmacological activity. 12 On the other hand, the hebertane sesquiterpene hebertenolide, which contains a cyclopentane-fused chromanone, is a biologically active compound. 13 In continuation of our investigation in searching for MCRs, 14 we decided to explore the idea that trapping of acetylenecarboxylate−isocyanide zwitterionic intermediates with 3acetyl-2H-chromen-2-ones might be hopeful in gaining access to new types of chromanones, annulated-cyclopentadiene moieties, via a three-component reaction.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Chromone and coumarin derivatives have been found to exhibit a broad range of biological activities such as antiviral, antimicrobial, and antitumor ones . The 3,4-dihydrocoumarin system is widely distributed in nature, and some derivatives have been shown to exhibit pharmacological activity . On the other hand, the hebertane sesquiterpene hebertenolide, which contains a cyclopentane-fused chromanone, is a biologically active compound…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Cyclopentadiene-Fused Chromanones via One-Pot Multicomponent Reactions

2013

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We have developed one-pot method for the synthesis of functionalized novel cyclopentadiene-fused chromanone scaffolds. A variety of 4-oxo-2,4-dihydrocyclopenta[c]chromene-1,2-dicarboxylates were obtained in moderate to good yields via condensation of 2-hydroxybenzaldehydes and ethyl acetoacetate with 1:1 acetylenecarboxylate-isocyanides in toluene. These reactions presumably proceed via reaction of the in situ generated 3-acetyl-2H-chromen-2-ones with acetylenecarboxylate-isocyanide zwitterionic intermediates through Michael addition/intramolecular cyclization and double [1,5] acyl shift rearrangement cascade.

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“…Phenols or anilines, were able to act as nucleophiles towards cinnamic acids in the presence of Lewis acids or palladium catalyst. Tilve and Aubé independently reported the construction of dihydrocoumarins via Michael addition of the ortho carbon of phenols followed by cyclization. Phenols bearing electron‐donating groups (OMe, OH, Me) could smoothly transform into the corresponding products in good yields.…”

Section: Michael Additionmentioning

confidence: 99%

Recent Advances of Cinnamic Acids in Organic Synthesis

et al. 2020

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The great success of cinnamic acids was rooted in their multiple functional groups. Herein, reactions triggered by the radical addition, electrophilic addition, Michael addition and reactions of acids were thoroughly discussed and summarized. Multi-component reactions, rearrange-ments, stereoselective synthesis, coupling, additions will be depicted in detail. This review focused on advances of cinnamic acids in the last decade (2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). We hope this review will be good for a better understanding of these reagents and future research. * , [7,8] acyl [9] and ketonic [10] radicals were reported. Toluene, [8a-c,9] boron reagents, [8d] aldehydes, [8e] acids, [9b,c] amides, [9d,12e-f] ketones, [10a-b] ethers, [11a-c] alcohols, [12a] epoxides, [12b] nitriles [12a] were able to function as radical precursors.Mao and co-workers [4] reported the decarboxylative methylation of cinnamic acids. The DTBP was employed not only as the oxidant, but also as the methyl source.C vinyl À CF 3 compounds (like Panomifene, and Cyhalothrin) were useful in medicinal chemistry. [5b] Hence, numerous efforts have been devoted to the preparation of these compounds. In this decade, several applications of air-stable Togni's reagent [5a-c,6a] or NaSO 2 CF 3 [5d-f,6b] for the direct C vinyl À CF 3 construction from cinnamic acids have been reported. These radical addition and decarboxylative methods usually required a metal-catalyst (Ir, [5a] Cu [5c,e,6b] ) (Scheme 3)Hu and co-workers [6a] presented a protocol for the construction of C sp2 À CF 2 SO 2 R bonds with a Togni-type reagent. The [a] L.Scheme 1. Classification by mechanism Scheme 2. Radical cascade.

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Solvent-free synthesis of 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling of phenols with cinnamic acid catalyzed by molecular iodine

Cited by 20 publications

References 24 publications

Iodine-catalyzed three component reaction: a novel synthesis of 2-aryl-imidazo[1,2-a]pyridine scaffolds

Iodine-catalyzed three component reaction: a novel synthesis of 2-aryl-imidazo[1,2-a]pyridine scaffolds

Synthesis of Cyclopentadiene-Fused Chromanones via One-Pot Multicomponent Reactions

Recent Advances of Cinnamic Acids in Organic Synthesis

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