scholarly journals Simple one-pot synthesis of thioureas from amine, carbon disulfide and oxidants in water

2016 ◽  
Vol 81 (3) ◽  
pp. 219-231 ◽  
Author(s):  
Milutin Milosavljevic ◽  
Ivan Vukicevic ◽  
Sasa Drmanic ◽  
Jasmina Nikolic ◽  
Aleksandar Marinkovic ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Carbon Disulfide ◽  
Reaction Times ◽  
Tetraacetic Acid ◽  
Reaction Conditions ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Industrial Level ◽  
By Products ◽  
Operational Simplicity

The present study reports the new facile methodology for synthesis of symmetrical and asymmetrical thioureas by an one-pot reaction of amine, carbon disulfide and oxidants: hydrogen peroxide, ethylenediamine tetraacetic acid (EDTA)/sodium percarbonate system or air. The structures of the synthesized compounds were confirmed by IR, 1H and 13C NMR and MS methods. Reaction mechanism has been proposed on the basis of reaction intermediate isolation and their structure determination. The synthetic benefits of the presented methods is reflected in the operational simplicity, mild reaction conditions, short reaction times, recycling of solvent, high purity and yield of products, absence of dangerous by-products and technological applicability at industrial scale. Considering commercial importance of the thioureas, it can be emphasized that implementation of the optimal synthesis of thiourea, based on presented methods, at industrial level of production would provide concurrent alternative to existing technologies in use.

A Facile and Convenient Approach for the Synthesis of Novel Sesamol–Oxazine and Quinoline–Oxazine Hybrids

2017 ◽  
Vol 70 (12) ◽  
pp. 1285 ◽  
Author(s):  
Garima Khanna ◽  
Pooja Saluja ◽  
Jitender M. Khurana
Keyword(s):  
Spectral Data ◽  
Aromatic Amines ◽  
Reaction Times ◽  
The Novel ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Convenient Approach ◽  
High Yields ◽  
Operational Simplicity

A series of functionalized sesamol–oxazine and quinoline–oxazine hybrids have been synthesized via one-pot reaction of sesamol/6-hydroxyquinoline, aromatic amines, and methanal. The structures of all the novel compounds were confirmed by spectral data. The structures of the synthesized hybrids were also confirmed by X-ray crystallographic studies. Mild reaction conditions, operational simplicity, short reaction times, simple workup, and high yields of products are salient features of this methodology.

scholarly journals New method for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropylthiocarbamates by oxidation of ammonium salt of xhantogenic acid

2010 ◽  
Vol 64 (5) ◽  
pp. 401-409 ◽  
Author(s):  
Smiljka Milisavljevic ◽  
Aleksandar Marinkovic ◽  
Milutin Milosavljevic
Keyword(s):  
Hydrogen Peroxide ◽  
Ammonium Salt ◽  
Sodium Hypochlorite ◽  
Reaction Times ◽  
Synthetic Methods ◽  
Molar Ratio ◽  
Reaction Conditions ◽  
Optimal Method ◽  
Sodium Ethyl ◽  
Industrial Level

A synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates by oxidation of ammonium salt of ethyl and isopropylxanthogenic acid in a presence of sodium hypochlorite and hydrogen peroxide were performed. Ammonium salt of ethyl and isopropylxanthogenic acid was obtained by the reaction of alkylammonium sulfate and sodium ethyl and isopropyl xanthate. Studies on a dependence of N-ethyl-O-isopropylthiocarbamate yield and purity with respect to reaction parameters (reaction time, molar ratio of oxidant and ethylamonium salt of isopropylxanthogenic acid) were performed. Optimal reaction conditions for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates were established. Synthesized compounds have been fully characterized by FTIR, 1H NMR and MS data, while purity has been determined by GC method. A plausible pathway for the N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates synthesis, in the presence of the oxidative agents sodium hypochlorite and hydrogen peroxide, was proposed. The presented synthetic methods has been developed at laboratory and applied at semi-industrial level. The developed optimal method provides a powerful and versatile method for the preparation of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates. This new optimized method offer several benefits, namely, simple operation, mild reaction conditions, bypass of hazardous organic solvents, moderately toxic and inexpensive reagents, and also short reaction times and high product yields.

Synthesis of Highly Functionalized Quinazoline-2,4(1H,3H)-diones from Isocyanides, Aniline and Isocyanate via Cu-Catalyzed Intermolecular C-H Activation Reactions

2020 ◽  
Vol 17 (11) ◽  
pp. 832-836
Author(s):  
Manijeh Nematpour ◽  
Hossein Fasihi Dastjerdi ◽  
Mehdi Jahani ◽  
Sayyed Abbas Tabatabai
Keyword(s):  
13C Nmr ◽  
Reaction Times ◽  
High Yield ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Activation Reaction ◽  
Elemental Analyses

A simple and appropriate procedure for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives from isocyanides, aniline and isocyanate via the Cu-catalyzed intramolecular C-H activation reaction is reported. The advantages of this method are one-pot conditions, accessible starting materials- catalyst, high yield of products, and short reaction times. The structures are confirmed spectroscopically (1H- and 13C-NMR, IR and EI-MS) and by elemental analyses.

scholarly journals The Role Ionic Liquid [BMIM][PF6] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier–Prins Reaction

Molecules ◽  
2019 ◽  
Vol 24 (11) ◽  
pp. 2084
Author(s):  
Poliane K. Batista ◽  
João Marcos G. de O. Ferreira ◽  
Fabio P. L. Silva ◽  
Mario L. A. A Vasconcellos ◽  
Juliana A. Vale
Keyword(s):  
Ionic Liquid ◽  
Yield Loss ◽  
Allyl Bromide ◽  
Reaction Times ◽  
Prins Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Barbier Reaction ◽  
Significant Yield

Tetrahydropyran (THP) rings are common in several natural products, therefore, various strategies are being developed to synthesize these rings. The present work described the study of a one-pot synthesis of 2,4,6-trisubstituted tetrahydropyran compounds promoted by the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate [BMIM][PF6] through a Barbier–Prins reaction between allyl bromide and aldehydes. The use of [BMIM][PF6] gave Prins products from several aldehydes in good yields and reaction times. We also found that the anion, PF6-, accelerates the Barbier reaction when used alone, and the excess SnBr2 from the reaction conditions of the Barbier reaction leads to the formation of the THP rings, thus acting as a catalyst for Prins cyclization. Additionally, we demonstrate that ionic liquid can be recovered and reused five times in the preparation of 4-bromo-tetrahydro-2,6-diphenyl-2H-pyran without significant yield loss.

Nanofibre Sepiolite Catalyzed Green and Rapid Synthesis of 2-Amino-4H-chromene Derivatives

2018 ◽  
Vol 71 (1) ◽  
pp. 32 ◽  
Author(s):  
Arezou Mohammadinezhad ◽  
Batool Akhlaghinia
Keyword(s):  
Column Chromatography ◽  
Present Method ◽  
Simple Procedure ◽  
Reaction Times ◽  
Significant Decline ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Rapid Synthesis ◽  
One Pot ◽  
Highly Efficient

Nanofibre sepiolite catalyzed the rapid, clean, and highly efficient synthesis of 2-amino-4H-chromene derivatives by a one-pot, three-component condensation of a series of aldehydes, various enolizable C–H bonds (such as dimedone, α-naphthol, resorcinol, and 4-hydroxy-2H-chromen-2-one), and malononitrile in a mixture of water/ethanol. The present method offers several advantages such as high to excellent yields, short reaction times, mild reaction conditions, simple procedure, use of inexpensive, non-toxic, and naturally available catalyst, easy isolation of the products, and no need for column chromatography. The catalyst could be easily separated from the reaction mixture and can be reused for many consecutive trials without a significant decline in its reactivity.

Tributylhexadecylphosphonium bromide: an efficient reagent system for the one-pot synthesis of 2,4,5-trisubstituted imidazoles

2015 ◽  
Vol 21 (2) ◽  
Author(s):  
Mohammad Heidari ◽  
Mohsen Rezaei ◽  
Rashid Badri
Keyword(s):  
Cost Effectiveness ◽  
Aromatic Aldehyde ◽  
Ammonium Acetate ◽  
Reaction Times ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One ◽  
Efficient Reagent

AbstractThe reaction of benzil, an aromatic aldehyde, and ammonium acetate in ethanol at reflux in the presence of tributylhexadecylphosphonium bromide as catalyst affords a 2,4,5-trisubstituted imidazole. The present methodology offers several advantages over the literature methods, including excellent yields, shorter reaction times, environmentally benign milder reaction conditions, cost-effectiveness of catalyst, easy workup, and purification of products by nonchromatographic methods.

scholarly journals Tandem Triphosgene-Assisted Metal-Free One-pot Preparation of Nitriles and Amides from Aldehydes and Ketones

2021 ◽  
Author(s):  
Jianguo liu ◽  
Xiu-Zhi Wei ◽  
Longlong Ma
Keyword(s):  
Metal Catalysts ◽  
Organic Base ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Aldehydes And Ketones ◽  
Ester Linkage ◽  
Hydrolysis Of ◽  
By Products

Here we report a facile and efficient triphosgene-assisted one-pot conversion of aldehydes/ketones into nitriles/amides. The triphosgene, a kind of phosgene alternative, containing both ester linkage and chloromethyl units, easily reacts with oximes for the preparation of nitriles/amides. However, the reaction of oximes with triphosgene can’t fully convert corresponding nitriles/amides due to hydrolysis of oximes to aldehydes or ketones. Our protocol tandem proceeds smoothly without the use of organic base and metal catalysts. Diverse functionalized aromatic, aliphatic, and allylic aldehydes/ketones incorporating biomass-derived platform compounds were successfully converted to nitriles and amides in excellent yields. Compared to step-by-step reaction, this tandem strategy is characterized by multi-step reaction in one pot, mild reaction conditions, and fewer by-products.

scholarly journals Comparative analysis of oxidative synthesis of N-alkyl, N,N-dialkyl and N-cykloalkyl-O-isobutyl thioncarbamate

2011 ◽  
Vol 65 (5) ◽  
pp. 541-549 ◽  
Author(s):  
Milica Sovrlic ◽  
Milutin Milosavljevic ◽  
Aleksandar Marinkovic ◽  
Jasmina Djukanovic ◽  
Danijela Brkovic ◽  
...  
Keyword(s):  
Molar Ratio ◽  
Scale Production ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Comparative Results ◽  
Industrial Level ◽  
Gas Chromatographic Method ◽  
First Time ◽  
Optimal Reaction ◽  
Yield And Purity

A optimized synthesis of N-alkyl, N,N-dialkyl- and N-cycloalkyl-O-isobutyl thioncarbamates by aminolysis of sodium isobutylxanthogenic acid (NaiBXAc) and primary, secondary and cycloalkyl amines was developed at laboratory scale and applied at semi-industrial level. Studies on dependence of N-n-propyl-O-isopropylthiocarbamate yield and purity with respect to reaction parameters: reaction time and molar ratio of n-propylamine and NaiBXAc, were performed. In such way, optimal reaction conditions for synthesis of N-alkyl, N,N-dialkyl- and N-cycloalkyl-O-isobutyl thioncarbamates, by aminolysis of NaiBXAc, were established. Also, comparative results of thioncarbamates synthesis starting from potassium isobutyl xanthate (KiBX) and corresponding amines in presence of different oxidants: hydrogen peroxide, sodium hypochlorite and new oxidative agent potassium peroxodisulfate were evaluated. Synthesized compounds have been fully characterized by FTIR, 1H and 13C NMR and MS data, elemental analysis and purity have been determined by gas chromatographic method (GC). According to our knowledge, ten synthesized thioncarbamates are for the first time characterized. Synthesized compounds could be used as selective reagents for flotation of copper and zinc ores. The presented methods offer several benefits, namely, high product yields and purity, simple operation, mild reaction conditions without use of hazardous organic solvents, while some of them could be implemented on industrial scale production.

Straightforward and Expeditious One-Pot Tandem Synthesis of 3,5-Diaryl-1,2,4-Selenadiazoles from Aryl Nitriles

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4279-4283
Author(s):  
Sahar Majnooni ◽  
Zainab Almansaf ◽  
Miu Tsuji ◽  
Ahmad R. Khosropour ◽  
Hassan Zali-Boeini ◽  
...  
Keyword(s):  
Efficient Synthesis ◽  
Oxidative Dimerization ◽  
Reaction Conditions ◽  
One Pot ◽  
Aryl Nitriles ◽  
Dimerization Reaction ◽  
Tandem Synthesis ◽  
Operational Simplicity

A one-pot process for the efficient synthesis of 3,5-diaryl-1,2,4-selenadiazoles from aryl nitriles has been developed. This tandem transformation was performed in excellent yields (91–98%) via in situ selenoamidation and a subsequent oxidative dimerization reaction. This method features relatively mild reaction conditions, operational simplicity, straightforward separation of the products, and the utilization of inexpensive reagents.

scholarly journals One-pot, three-component synthesis of pyrrolo[2,3-d]pyrimidine derivatives

2018 ◽  
Vol 62 (1) ◽  
Author(s):  
Jabbar Khalafy ◽  
Ramin Javahershenas
Keyword(s):  
Simple Procedure ◽  
Reaction Times ◽  
Pyrimidine Derivatives ◽  
Reaction Conditions ◽  
One Pot ◽  
General Applicability ◽  
Green Approach ◽  
Three Component Reaction ◽  
High Yields ◽  
Work Up

<p>A green approach for the synthesis of polyfunctionalized pyrrolo[2,3-<em>d</em>]pyrimidine derivatives was successfully achieved by a one-pot, three-component reaction of arylglyoxals, 6-amino-1,3-dimethyluracil and barbituric acid derivatives in the presence of tetra-<em>n</em>-butylammonium bromide (TBAB) (5 mol%) as the catalyst in ethanol at 50 °C. This protocol has many advantages such as high yields (73-95%), green and simple procedure, short reaction times, easy work-up, mild reaction conditions and general applicability.</p>

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