Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni's reagent.

ABSTRACT: A one-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates by the reaction of secondary amines, carbon disulfide and Togni's reagent is described. The reactions proceed in moderate to good yields. A similar reaction using a primary aliphatic amine afforded the corresponding isothiocyanate in high yield. A variable temperature NMR study revealed a rotational barrier of 14.6, 18.8, and 15.9 kcal/mol for the C-N bond in the dithiocarbamate moiety of piperidine, pyrrolidine, and diethylamine adducts, respectively. In addition, the calculated barriers of rotation are in reasonable agreement with the experiments.

SUBMITTER: Halimehjani AZ

PROVIDER: S-EPMC5704766 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

One-pot three-component route for the synthesis of <i>S</i>-trifluoromethyl dithiocarbamates using Togni's reagent.

Halimehjani Azim Ziyaei AZ Dračínský Martin M Beier Petr P

Beilstein journal of organic chemistry 20171124

A one-pot three-component route for the synthesis of <i>S</i>-trifluoromethyl dithiocarbamates by the reaction of secondary amines, carbon disulfide and Togni's reagent is described. The reactions proceed in moderate to good yields. A similar reaction using a primary aliphatic amine afforded the corresponding isothiocyanate in high yield. A variable temperature NMR study revealed a rotational barrier of 14.6, 18.8, and 15.9 kcal/mol for the C-N bond in the dithiocarbamate moiety of piperidine, p ...[more]

PMID: 29234477

Similar Datasets

One-pot, three-component arylalkynyl sulfone synthesis.

Project description:A one-pot three-component protocol for the preparation of arylsulfonyl alkynes through the reaction of ethynyl-benziodoxolone (EBX) reagents, DABSO (DABCO·SO2), and either organomagnesium reagents or aryl iodides with a palladium catalyst is reported. A broad range of aryl and heteroarylalkynyl sulfones were obtained in 46-85% overall yield.

| S-EPMC4342956 | biostudies-literature

DABSO-based, three-component, one-pot sulfone synthesis.

Project description:The addition of Grignard reagents or organolithium reagents to the SO2-surrogate DABSO generates a diverse set of metal sulfinates, suitable for direct conversion to sulfone products. The metal sulfinates can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums.

| S-EPMC3883144 | biostudies-literature

One-pot three component synthesis of 5-allyl-1,2,3-triazoles using copper(i) acetylides.

Project description:One-pot three-component reactions using copper(i) acetylide, azide, allyl iodide, and NaOH have been developed. The reactions proceed smoothly at room temperature to afford 5-allyl-1,2,3-triazoles, which can be further transformed into a variety of 1,2,3-triazole-fused bi-/tricyclic scaffolds. This method offers the most efficient, convenient, and practical route towards useful polycyclic scaffolds in moderate to excellent yields.

| S-EPMC9077393 | biostudies-literature

A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime.

Project description:Functionalized 3-trifluoromethyl-2-isoxazolines and 3-trifluoromethylisoxazoles were easily prepared from trifluoromethyl aldoxime 2 under mild conditions by using DIB as oxidant. Theoretical studies of the reactivity of trifluoroacetonitrile oxide 4 toward olefins and alkynes were carried out. The 3-trifluoromethyl-2-isoxazolines were ring-opened with NaBH4 and NiCl2 to yield the corresponding trifluoromethylated γ-amino alcohols.

| S-EPMC3869255 | biostudies-literature

Three-Component One-Pot Synthesis of Highly Functionalized Bis-Indole Derivatives.

Project description:In this study, we detail the development of a concise and efficient three-component protocol for the regioselective synthesis of highly functionalized bis-indoles through a one-pot, two-step sequential process starting from enaminones 1, indoles 2, and acenaphthylene-1,2-dione 3 that is catalyzed by piperidine and p-methyl benzenesulfonic acid. This protocol has several advantages including simplicity of experimental operation, high efficiency of bond formation, ready availability and low cost of starting materials, environmentally benign conditions, and target molecular diversity.

| S-EPMC6682060 | biostudies-literature

One-pot three-component synthesis of quinoxaline and phenazine ring systems using Fischer carbene complexes.

Project description:One-pot three-component coupling of o-alkynylheteroaryl carbonyl derivatives with Fischer carbene complexes and dienophiles leading to the synthesis of quinoxaline and phenazine ring systems has been investigated. This involves the generation of furo[3,4-b]pyrazine and furo[3,4-b]quinoxaline as transient intermediates, which were trapped with Diels-Alder dienophiles. This is the first report on furo[3,4-b]pyrazine intermediates.

| S-EPMC2900911 | biostudies-literature

One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines.

Project description:Novel triene merocyanines, i.e. 1-styryleth-2-enylidene and 4-(1,3,3-trimethylindolin-2-ylidene)but-2-en-1-ylideneindolones are obtained in good to excellent yields in a consecutive three-component insertion Sonogashira coupling-addition sequence. The selectivity of either series is remarkable and has its origin in the stepwise character of the terminal addition step as shown by extensive computations on the DFT level. All merocyanines display intense absorption bands in solution and the film spectra indicate J-aggregation. While 1-styryleth-2-enylideneindolones show an intense deep red emission in films, 4-(1,3,3-trimethylindolin-2-ylidene)but-2-en-1-ylideneindolones are essentially nonemissive in films or in the solid state. TD-DFT computations rationalize the charge-transfer nature of the characteristic broad long-wavelength absorptions bands.

| S-EPMC3999876 | biostudies-literature

Facile rhenium-peptide conjugate synthesis using a one-pot derived Re(CO)3 reagent.

Project description:We have synthesized two Re(CO)3-modified lysine complexes (1 and 2), where the metal is attached to the amino acid at the N? position, via a one-pot Schiff base formation reaction. These compounds can be used in the solid phase synthesis of peptides, and to date we have produced four conjugate systems incorporating neurotensin, bombesin, leutenizing hormone releasing hormone, and a nuclear localization sequence. We observed uptake into human umbilical vascular endothelial cells as well as differential uptake depending on peptide sequence identity, as characterized by fluorescence and rhenium elemental analysis.

| S-EPMC4991029 | biostudies-literature

One-pot three component synthesis of substituted dihydropyrimidinones using fruit juices as biocatalyst and their biological studies.

Project description:New and facile one-pot three component approach for the synthesis of substituted dihydropyrimidinones derivatives (4a-4h) from reaction of equimolar substituted aldehydes (1a-1h), methyl acetoacetate (2a) and urea (3a) in presence of nature derived catalyst viz. Cocos nucifera L. juice, Solanum lycopersicum L. juice and Citrus limetta juice, commonly known as coconut juice, tomato juice and musambi juice respectively, at room temperature has been carried out. All synthesized compounds were evaluated for in vitro herbicidal activity against Raphanus sativus L. (Radish seeds). The compounds (4a-4h) were also screened for their antifungal activity against Rhizoctonia solani and Colletotrichum gloeosporioides by poisoned food techniques method. Antibacterial activity was also studied against Erwinia cartovora and Xanthomonas citri by inhibition zone method. From activity data, it was found that compounds 4g and 4d were most active against Raphanus sativus L. (root) and Raphanus sativus L. (shoot) respectively. Compounds 4f and 4c was found most active against Rhizoctonia solani and Colletotrichum gloeosporioides fungus respectively at highest concentration. Compound 4g has shown maximum inhibition zone i.e. 1.00-5.50 mm against Erwinia cartovora at 2000 μg/mL concentration. Maximum Xanthomonas citrii growth was inhibited by compounds 4f showing inhibition zone 4.00-12.00 mm at highest concentration. Short reaction time, high yields, mild reaction condition and simple work-up are some merits of present methodology.

| S-EPMC7491738 | biostudies-literature

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions.

Project description:A catalyst-free one-pot synthetic methodology was developed for the preparation of 1,3,5-triazine-2,4-dithione derivatives through three-component reactions of arylaldehydes, thiourea, and orthoformates. The procedure tolerated a diverse range of arylaldehydes and orthoformates and provided a rapid entry to a variety of 4-aryl-6-(alkylthio)-3,4-dihydro-1,3,5-triazine-2(1H)-thiones (29 examples). The synthetic strategy relies on the dual role of thiourea in the cyclization with the aldehydes and the alkylation via an intermediate imidate formation. The structures of 1,3,5-triazine-2,4-dithione derivatives were characterized by spectroscopic techniques as well as by single crystal X-ray diffraction.

| S-EPMC7323627 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data