Diketene a Privileged Synthon in the Synthesis of Heterocycles. Part 2: Six-Membered Ring Heterocycles

Talaei, Bahareh; Heravi, Majid M.

doi:10.1016/bs.aihch.2017.10.004

Cited by 14 publications

(2 citation statements)

References 213 publications

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“…Heterocyclic compounds 31 , 32 synthesized through MCR 33 in the presence of heterogeneous catalysts in an aqueous medium are of particular importance 34 , 35 .…”

Section: Introductionmentioning

confidence: 99%

The preparation of polyvinyl imidazole-functionalized magnetic biochar decorated by silver nanoparticles as an efficient catalyst for the synthesis of spiro-2-Amino-4H-pyran compounds

Mohammadi

Heravi

Saljooqi

et al. 2022

Sci Rep

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The silver nanoparticle was synthesized by developing poly (1-vinylimidazole) on the surface of magnetized biochar (the stem and roots of Spear Thistle) (biochar/Fe3O4/PVIm/Ag). This nanocomposite was characterized by Fourier-transformed infrared spectroscopy (FTIR), powder X-ray diffraction (XRD), vibrating sample magnetometer (VSM), scanning electron microscopy-energy dispersive X-ray spectroscopy (SEM–EDS), and transmission electron microscopy (TEM). The SEM and TEM images of the nanocatalyst, biochar/Fe3O4/PVIm/Ag-NPs, confirmed the observation of microscopic sheets of biochar. The catalytic activity of these Ag NPs was tested via multicomponent reaction plus reusing to successful formation of 2-amino-4H-pyran and functionalized spirochromen derivatives. The prepared nanocatalyst was easily separated by an external magnet and reused in repeating coupling reaction cycles four times without remarkable activity loss. The catalyst showed great efficiency and reusability, thus making it an ideal candidate for catalytic purposes in several organic transformations.

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“…Heterocyclic compounds 31 , 32 synthesized through MCR 33 in the presence of heterogeneous catalysts in an aqueous medium are of particular importance 34 , 35 .…”

Section: Introductionmentioning

confidence: 99%

The preparation of polyvinyl imidazole-functionalized magnetic biochar decorated by silver nanoparticles as an efficient catalyst for the synthesis of spiro-2-Amino-4H-pyran compounds

Mohammadi

Heravi

Saljooqi

et al. 2022

Sci Rep

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“…Considering the above points and our continued interest in the one-pot synthesis of heterocyclic compounds − wherein iodine is used as a Lewis acid catalyst, we designed a five-component Hantzsch-type reaction (Figure ) to construct a novel molecule bearing a 2-amino-3,4-dihydropyran-3-carboxamide core. As a useful building block, ,,− diketene was applied as one of the starting materials to form carboxamides directly.…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective Synthesis of 3,4-Dihydropyran-3-carboxamides with in Vitro Anti-inflammatory Activity

Zeng

Huang

et al. 2019

ACS Comb. Sci.

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A versatile and economical reaction of diketene (1), aryl amines 2, cyclic 1,3-diketones 3, primary amines 4, and aryl aldehydes 5 was explored to synthesize 3,4-dihydropyran-3-carboxamide derivatives under mild conditions. Three stereogenic centers are generated in the products, and the structure of the major diastereomer of 6{1,1,3,1} was identified by X-ray diffraction and 2D NMR spectroscopy. The scope and limitation investigation provided two series of (2S,3R,4S)-chromene-3-carboxamides in good to excellent yields with high diastereoselectivity. Two products, 6{5,3,1,1} and 6{7,3,1,1}, exhibited in vitro anti-inflammatory activity with significant inhibition of pro-inflammatory cytokine IL-6 and TNF-α expression in lipopolysaccharide (LPS)-treated Raw 264.7 cells.

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Iodine‐Catalyzed One‐Pot Four‐Component Synthesis of Spiro[indoline‐3,4′‐pyrano‐pyrazole] Derivatives

Rezvanian

Zadsirjan

Saedi

et al. 2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).An efficient, facile, and useful synthetic method was developed for the production of spiro[indoline-3,4 0pyrano-pyrazole] carbonitrile derivatives through a one-pot, four-component reaction involving hydrazine hydrate, diketene, substituted isatins, and malononitrile or ethyl cyanoacetate in the presence of iodine as the efficient catalyst in ethanol at room temperature. Significantly, this remarkable method provides novel spiropyranopyrazole derivatives in good to high yields. The significant aspects of this protocol are facile work-up approach and a greener process because the use of toxic and hazardous solvents are avoided. 6 0 -Amino-5-chloro-3 0 -methyl-2-oxo-1 0 H-spiro[indoline-3,4 0pyrano[2,3-c]pyrazole]-5 0 -carbonitrile (2e).White powder, mp = 295-294°C, 0.28 g, yield: 85%. IR (KBr) (ν max , cm À1 ): 3386 and 3347 (NH 2 ), 3137 (2NH), 2182 (CN), December 2018One-Pot Four-Component Synthesis of Spiro[indoline-3,4 0 -pyrano-pyrazole] Derivatives 2777

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Diketene a Privileged Synthon in the Synthesis of Heterocycles. Part 2: Six-Membered Ring Heterocycles

Cited by 14 publications

References 213 publications

The preparation of polyvinyl imidazole-functionalized magnetic biochar decorated by silver nanoparticles as an efficient catalyst for the synthesis of spiro-2-Amino-4H-pyran compounds

The preparation of polyvinyl imidazole-functionalized magnetic biochar decorated by silver nanoparticles as an efficient catalyst for the synthesis of spiro-2-Amino-4H-pyran compounds

Diastereoselective Synthesis of 3,4-Dihydropyran-3-carboxamides with in Vitro Anti-inflammatory Activity

Iodine‐Catalyzed One‐Pot Four‐Component Synthesis of Spiro[indoline‐3,4′‐pyrano‐pyrazole] Derivatives

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