Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Tunable Synthesis of Disulfide-Functionalized Enaminones and 1,4-Thiazines via the Reactions of Enaminones and ?-Aminoethanethiol.

ABSTRACT: The reactions of ?-aminoethanethiol with N,N-dimethyl enaminones are performed to selectively provide disulfide-functionalized enaminones and 1,4-thiazines. By performing the reaction in water and catalyst-free conditions, the transamination and oxidative S-S coupling between the two substrates take place to give disulfide-functionalized enaminones. On the other hand, by using identical starting materials, the employment of the CuI catalyst in dimethyl sulfoxide enables the selective generation of 1,4-thiazines via tandem transamination and C(sp²)-H bond thiolation.

SUBMITTER: Gao Y

PROVIDER: S-EPMC6645214 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Tunable Synthesis of Disulfide-Functionalized Enaminones and 1,4-Thiazines via the Reactions of Enaminones and β-Aminoethanethiol.

Gao Yong Y Hu Changfeng C Wen Chengping C Wan Jie-Ping JP

ACS omega 20171110 11

The reactions of β-aminoethanethiol with <i>N</i>,<i>N</i>-dimethyl enaminones are performed to selectively provide disulfide-functionalized enaminones and 1,4-thiazines. By performing the reaction in water and catalyst-free conditions, the transamination and oxidative S-S coupling between the two substrates take place to give disulfide-functionalized enaminones. On the other hand, by using identical starting materials, the employment of the CuI catalyst in dimethyl sulfoxide enables the selecti ...[more]

PMID: 31457336

Similar Datasets

Divergent synthesis of dual 1,4-dihydropyridines with different substituted patterns from enaminones and aldehydes through domino reactions.

Project description:A concise and efficient protocol for the regioselective synthesis of dual 1,4-dihydropyridines with several substituted patterns has been developed from a cascade cyclization of enaminones and aldehydes in different media (EtOH/CH3CN). The one-pot cascade reaction involves at least five reactive sites and generates multiple C-C and C-N bonds. The established protocol explores the chemistry of enaminones by employing their three reactive sites. The method has several advantages including mild conditions, operational simplicity, and high bond-forming efficiency. It may offer promise in a variety of biochemical applications.

| S-EPMC9079339 | biostudies-literature

Synthesis of saturated 1,4-benzodiazepines via Pd-catalyzed carboamination reactions.

Project description:A new synthesis of 1,4-benzodiazepines and 1,4-benzodiazepin-5-ones is reported. The Pd-catalyzed coupling of N-allyl-2-aminobenzylamine derivatives with aryl bromides affords the heterocyclic products in good yield, and substrates bearing allylic methyl groups are transformed to cis-2,3-disubstituted products with >20:1 dr.

| S-EPMC3084890 | biostudies-literature

Synthesis of mono-functionalized S-diazocines via intramolecular Baeyer-Mills reactions.

Project description:Herein we report a reliable method to synthesize mono-functionalized S-diazocines in reproducible yields via intramolecular Baeyer-Mills reactions. Diazocines exhibit excellent photoswitchable properties. As opposed to azobenzenes they are more stable in their cis configuration. Particularly in photopharmacology mono-functionalized diazocines should be potentially useful and superior to the frequently used azobenzenes because the sterically more demanding cis configuration should be inactive, and the slender trans configuration should fit in a tight binding pocket of a receptor. Hence, it should be possible to administer the stabile inactive compound and switch it on at the site of illness with visible light. To date only a limited number of diazocine derivatives have been published of which most are symmetrically functionalized. Using the Baeyer-Mills reaction for the synthesis of diazocines opens a novel and convenient access to unsymmetrically substituted diazocines.

| S-EPMC6244113 | biostudies-literature

Three-component synthesis of cyclic enaminones via ketene cyclization.

Project description:Cyclic six-membered enaminones were synthesized from three components (bromodiazoacetone, primary amine, and alkyne) in high yields via aza-Michael addition, Wolff rearrangement, and nucleophilic ketene cyclization.

| S-EPMC3099226 | biostudies-literature

Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions.

Project description:[reaction: see text] The palladium-catalyzed carboamination of N-protected gamma-aminoalkenes with aryl bromides and triflates has been achieved under new, mild reaction conditions using the weak base Cs(2)CO(3) in dioxane solvent. These reactions tolerate a wide variety of functional groups, including enolizable ketones, nitro groups, methyl esters, and acetates, which are not compatible with previously described conditions.

| S-EPMC2758105 | biostudies-literature

Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions.

Project description:An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki-Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.

| S-EPMC8434198 | biostudies-literature

Acetone/Isopropanol Photoinitiating System Enables Tunable Disulfide Reduction and Disulfide Mapping via Tandem Mass Spectrometry.

Project description:Herein, we report the development of a new photochemical system which enables rapid and tunable disulfide bond reduction and its application in disulfide mapping via online coupling with mass spectrometry (MS). Acetone, a clean and electrospray ionization (ESI) compatible solvent, is used as the photoinitiator (1% volume) in the solvent system consisting of 1:1 alkyl alcohol and water. Under ultraviolet (UV) irradiation (?254 nm), the acetone/alcohol system produces hydroxyalkyl radicals, which are responsible for disulfide bond cleavage in peptides. Acetone/isopropanol is most suitable for optimizing the disulfide reduction products, leading to almost complete conversion in less than 5 s when the reaction is conducted in a flow microreactor. The flow microreactor device not only facilitates direct coupling with ESI-MS but also allows fine-tuning of the extent of disulfide reduction by varying the UV exposure time. Near full sequence coverage for peptides consisting of intra- or interchain disulfide bonds has been achieved from complete disulfide reduction and online tandem mass spectrometry (MS/MS) via low energy collision-induced dissociation. Coupling different degrees of partial disulfide reduction with ESI-MS/MS allows disulfide mapping as demonstrated for characterizing the three disulfide bonds in insulin.

| S-EPMC6310128 | biostudies-literature

Synthesis of new functionalized thiazolo pyridine-fused and thiazolo pyridopyrimidine-fused spirooxindoles via one-pot reactions.

Project description:A sequential multi-component reaction of the nitroketene dithioacetals, cysteamine hydrochloride, isatin and different CH-acids is described. This efficient method provides new functionalized thiazolo pyridine-fused spirooxindoles and thiazolo pyridopyrimidine-fused spirooxindoles in good yields. In the case of using isatin derivatives (5-bromoisatin and 5-chloroisatin), the reaction was carried out by using nano-SiO2 (20 mol%) as an effective heterogeneous Lewis acid promoter. This type of reaction provides a range of skeletally different polycyclic spiro thiazole-based heterocyclic structures and represents attractive advantages including straightforward one-pot operation under the catalyst-free condition and simple workup procedures without using tedious purification procedure.

| S-EPMC7114753 | biostudies-literature

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes.

Project description:In the presence of p-toluenesulfonic acid as catalyst the domino reaction of arylamines, methyl propiolates and aromatic aldehydes in ethanol proceeded smoothly to give polysubstituted 1,2,3,4-tetrahydroquinolines in moderate yields. The reaction is believed to involve the Povarov reaction of in situ generated β-enamino ester with the in situ formed aromatic imine.

| S-EPMC3511020 | biostudies-literature

Stereoselective synthesis of highly functionalized alpha-diazo-beta-ketoalkanoates via catalytic one-pot Mukaiyama-Aldol reactions.

Project description:Methyl diazoacetoacetate undergoes zinc triflate catalyzed condensation with a broad selection of aldehydes to produce delta-siloxy-alpha-diazo-beta-ketoalkanoates in good yield, and delta-hydroxy-alpha-diazo-beta-ketoalkanoates are formed with high diastereoselectivity in reactions with alpha-diazo-beta-ketopentanoate promoted by dibutylboron triflate.

| S-EPMC2829718 | 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