Synthesis of dithiocarbamate by Markovnikov addition reaction in aqueous medium

Halimehjani, Azim Ziyaei; Marjani, Katayoun; Ashouri, Akram

doi:10.1039/c004711b

Cited by 73 publications

(28 citation statements)

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“…As a part of our continued interest in the development of practical, safe, and environmentally friendly procedures for some important organic transformations and synthesis of chromenes , a convenient and facile one‐pot three‐component method for the synthesis of 4 H ‐chromenes in the presence of ZrOCl 2 ·8H 2 O as catalyst in water under thermal condition has been described (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

One‐pot Three‐component Route for the Synthesis of Functionalized 4H‐chromenes Catalyzed by ZrOCl₂·8H₂O in Water

Halimehjani

Keshavarzi

2018

Journal of Heterocyclic Chem

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An efficient method for the synthesis of functionalized 4H‐chromenes via a one‐pot three‐component condensation reaction of a 2‐hydroxybenzaldehyde with an active methylene compound and a carbon‐based nucleophile in the presence of a catalytic amount of ZrOCl2·8H2O in water under thermal condition has been described. High yields, simple work‐up procedure, performing reactions in water and synthesis of complex molecules with a one‐pot procedure are the main advantages of this procedure. In addition, the structure of the product from the condensation of salicylaldehyde, 2‐naphthol, and dimedone was confirmed by X‐ray crystallography.

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Section: Resultsmentioning

confidence: 99%

One‐pot Three‐component Route for the Synthesis of Functionalized 4H‐chromenes Catalyzed by ZrOCl₂·8H₂O in Water

Halimehjani

Keshavarzi

2018

Journal of Heterocyclic Chem

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“…Synthesis of Sodium Salts of Diethyl Dithiocarbamate Ligand: The preparation of dithiocarbamate ligands is reported elsewhere . Diethylamine (100 mmol) and sodium hydroxide (100 mmol) were dissolved in ethanol (100 cm 3 ) and stirred at 0 °C.…”

Section: Methodsmentioning

confidence: 99%

“…The preparation of dithiocarbamate ligands is reported elsewhere. [56] Diethylamine (100 mmol) and sodium hydroxide (100 mmol) were dissolved in ethanol (100 cm 3 ) and stirred at 0°C. Carbon disulfide (100 mmol) was added drop wise to the above stirred mixture.…”

Section: Synthesis Of Sodium Salts Of Diethyl Dithiocarbamate Ligandmentioning

confidence: 99%

Structure Elucidation of an Yttrium Diethyldithiocarbamato‐Phenanthroline Complex by X‐ray Crystallography, Solid‐State NMR, and ab‐initio Quantum Chemical Calculations

et al. 2016

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We present a structural analysis method for molecular and electronic structure of yttrium diethyldithiocarbamato‐phenanthroline complex {[Y(S2CNR2)3PHEN] with R = C2H5 and PHEN = 1,10‐phenanthroline} combining solid‐state NMR spectroscopy, XRD, and first principles DFT calculations. Replacing the Nd3+ ion with Y3+ in the reported crystal structure of [Nd(S2CNR2)3PHEN] complex generated an approximate 3D structure of the title complex. The structure was then subjected to first principles quantum chemical geometry optimisation using periodic DFT method. The quality of the method is discussed by comparing predicted and experimental powder XRD patterns. Full assignment of 13C and 15N solid‐state CP‐MAS NMR spectra as well as analyses of the principal values of the chemical shift tensors were carried out using periodic scalar relativistic DFT modelling. Spin‐orbit relativistic effects, estimated by SO‐ZORA formalism for one molecular unit, were evaluated. Finally, the X‐ray structure of the title complex was determined, which proved that the former procedure is appropriate. The most important orbital interactions were investigated by Natural Bond Orbital analysis. The isotropic shielding values for S2CN‐carbons were analysed by Natural Localised Molecular Orbital analysis. The present approach can be further extended to study other rare earth metal complexes, particularly those having similar but not yet solved crystal structures.

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“…The development of simple, versatile, and environmentally friendly processes or methodologies for widely used organic compounds from readily available reagents is one of the major challenges for chemists in organic synthesis [1][2][3][4][5][6][7]. Synthesis of organic molecules via green, mild, and simple procedures is currently receiving considerable attention.…”

Section: Introductionmentioning

confidence: 99%

A facile and efficient one-pot synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives in water

Mehrabi

Esfandiarpour

2015

J IRAN CHEM SOC

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explored as new materials because of their superconducting, optical, and electronic switching properties [17][18][19][20][21][22][23].The majority of the reactions between carbon disulfide and N-nucleophiles involve addition of carbon disulfide to N-H bonds. The products of these reactions, dithiocarbamate salts, reacts with epoxides [24, 25], 2-chloro-1,3-dicarbonyl compounds [26], chloroacetic acid [27], diethyl 2-chloromalonate [28], ethyl bromopyruvate [29], α-haloketones [30], 3,4-dihydro-2H-pyran [31], electrondeficient alkenes [32], β-nitrostyrene derivatives [33], dibenzoylacetylene [34], quinones [35], and itaconic anhydride [36] that can be transformed into dithiocarbamate derivatives.To the best of our knowledge, there has not been any report on the reaction between carbon disulfide and amines in the presence of arylidenemalononitriles. Herein, we report a one-pot three-component synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitriles from amines, carbon disulfide, and arylidenemalononitriles as starting materials. ExperimentalAll chemicals were purchased from Aldrich and Merck with high-grade quality and were used without any purification. All melting points were obtained on a Barnstead Electrothermal 9200 apparatus and are uncorrected. The reactions were monitored by TLC, and all yields refer to isolated products. 1 H and 13 C NMR spectra were recorded in DMSO-d 6 on a Bruker 400 MHz spectrometer. Infrared spectra were recorded on a Bruker FT-IR Equinax-55 spectrophotometer in KBr with absorption in cm −1 . Elemental analyses were performed using a Carlo Erba EA 1108 instrument. All products were characterized by their spectral and physical data.Abstract A one-pot three-component synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitriles from amines, carbon disulfide, and arylidenemalononitriles in H 2 O under reflux conditions, in good yields, is described.

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Synthesis of dithiocarbamate by Markovnikov addition reaction in aqueous medium

Cited by 73 publications

References 59 publications

One‐pot Three‐component Route for the Synthesis of Functionalized 4H‐chromenes Catalyzed by ZrOCl₂·8H₂O in Water

One‐pot Three‐component Route for the Synthesis of Functionalized 4H‐chromenes Catalyzed by ZrOCl₂·8H₂O in Water

Structure Elucidation of an Yttrium Diethyldithiocarbamato‐Phenanthroline Complex by X‐ray Crystallography, Solid‐State NMR, and ab‐initio Quantum Chemical Calculations

A facile and efficient one-pot synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives in water

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Synthesis of dithiocarbamate by Markovnikov addition reaction in aqueous medium

Cited by 73 publications

References 59 publications

One‐pot Three‐component Route for the Synthesis of Functionalized 4H‐chromenes Catalyzed by ZrOCl2·8H2O in Water

One‐pot Three‐component Route for the Synthesis of Functionalized 4H‐chromenes Catalyzed by ZrOCl2·8H2O in Water

Structure Elucidation of an Yttrium Diethyldithiocarbamato‐Phenanthroline Complex by X‐ray Crystallography, Solid‐State NMR, and ab‐initio Quantum Chemical Calculations

A facile and efficient one-pot synthesis of 6-amino-2-oxo-4-aryl-4H-1,3-dithiine-5-carbonitrile derivatives in water

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One‐pot Three‐component Route for the Synthesis of Functionalized 4H‐chromenes Catalyzed by ZrOCl₂·8H₂O in Water

One‐pot Three‐component Route for the Synthesis of Functionalized 4H‐chromenes Catalyzed by ZrOCl₂·8H₂O in Water