Browse
Submit Data
Databases
API
Help

Dataset Information

26 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-pot phosphine-catalyzed syntheses of quinolines.

ABSTRACT: In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the ?-phosphonium enoate ?-vinyl anion generated in situ through nucleophilic addition of PPh(3) to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile N-tosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.

SUBMITTER: Khong S

PROVIDER: S-EPMC3459651 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

One-pot phosphine-catalyzed syntheses of quinolines.

Khong San S Kwon Ohyun O

The Journal of organic chemistry 20120906 18

In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the β-phosphonium enoate α-vinyl anion generated in situ through nucleophilic addition of PPh(3) to the activated alkyne. Michae ...[more]

PMID: 22928667

Similar Datasets

One-pot syntheses of immunostimulatory glycolipids.

Project description:Glycolipids containing alpha-linked galactosyl and glucosyl moieties have been shown to possess unique immunostimulatory activity creating a need for access to diverse and anomerically pure sources of these compounds for immunological studies. To meet this demand, glycosyl iodides were enlisted in the synthesis of these biologically relevant glycoconjugates. In the first-generation protocol, per-O-benzyl galactosyl iodide was efficiently coupled with activated sphingosine acceptors, but fully functionalized ceramides were found to be unreactive. To overcome this obstacle, per-O-trimethylsilyl glycosyl iodides were investigated and shown to undergo highly efficient coupling with ceramide and glycerol ester acceptors. Contrary to what has been observed with other donors, we detected little difference between the reactivity of glucosyl and galactosyl iodides. The trimethylsilyl protecting groups play a dual role in activating the donor toward nucleophilic attack while at the same time providing transient protection: the silyl groups are readily removed upon methanolysis. All reactions proceeded with complete acceptor regioselectivity, eliminating the need for additional protecting group manipulations, and the desired alpha-anomers were formed exclusively. This three-step, one-pot synthetic platform provides rapid access to an important class of immunostimulatory molecules including the first reported synthesis of the glucosyl analogue of the bacterial antigen BbGL-II.

| S-EPMC2912955 | biostudies-literature

One-pot syntheses of irida-polycyclic aromatic hydrocarbons.

Project description:Metalla-analogues of polycyclic aromatic hydrocarbons (PAHs) have captivated chemists with their fascinating structures and unique electronic properties. To date, metallabenzene, metallanaphthalene and metallaanthracene have been reported. Metalla-analogues with more complicated fused rings have rarely been reported. Herein, we have successfully synthesized a series of new iridafluoranthenes and fused-ring iridafluoranthenes ranging from pentacyclic to heptacyclic metallaaromatic hydrocarbons in high yields under mild reaction conditions for the first time. Their photophysical and redox properties were also explored using UV-vis spectroscopy and electrochemistry combined with TD-DFT calculations. The present work may offer an important guideline for the design and construction of new polycyclic metallaaromatic hydrocarbons and metalla-nanographenes.

| S-EPMC7046080 | biostudies-literature

Selective One-Pot Syntheses of Mixed Silicon-Germanium Heteroadamantane Clusters.

Project description:Six Gey alloys are emerging materials for modern semiconductor technology. Well-defined model systems of the bulk structures aid in understanding their intrinsic characteristics. Three such model clusters have now been realized in the form of the Six Gey heteroadamantanes [0], [1], and [2] through selective one-pot syntheses starting from Me2 GeCl2 , Si2 Cl6 , and [nBu4 N]Cl. Compound [0] contains six GeMe2 and four SiSiCl3 vertices, whereas one and two of the GeMe2 groups are replaced by SiCl2 moieties in compounds [1] and [2], respectively. Chloride-ion-mediated rearrangement quantitatively converts [2] into [1] at room temperature and finally into [0] at 60 °C, which is not only remarkable in view of the rigidity of these cage structures but also sheds light on the assembly mechanism.

| S-EPMC8596519 | biostudies-literature

A one-pot multicomponent strategy for stereospecific construction of tricyclic pyrrolo[1,2-a]quinolines.

Project description:A novel multicomponent strategy for the efficient synthesis of tricyclic pyrrolo[1,2-a]quinolines has been described. The bond-forming efficiency, accessibility and generality of this synthesis make it highly attractive to assemble tri-heterocyclic scaffolds.

| S-EPMC3529132 | biostudies-literature

Chain-end-functionalized polyphosphazenes via a one-pot phosphine-mediated living polymerization.

Project description:A simple polymerization of trichlorophosphoranimine (Cl3 P = N-SiMe3 ) mediated by functionalized triphenylphosphines is presented. In situ initiator formation and the subsequent polymerization progress are investigated by (31) P NMR spectroscopy, demonstrating a living cationic polymerization mechanism. The polymer chain lengths and molecular weights of the resulting substituted poly(organo)phosphazenes are further studied by (1) H NMR spectroscopy and size exclusion chromatography. This strategy facilitates the preparation of polyphosphazenes with controlled molecular weights and specific functional groups at the α-chain end. Such well-defined, mono-end-functionalized polymers have great potential use in bioconjugation, surface modification, and as building blocks for complex macromolecular constructs.

| S-EPMC4115175 | biostudies-literature

Phosphine/palladium-catalyzed syntheses of alkylidene phthalans, 3-deoxyisoochracinic acid, isoochracinic acid, and isoochracinol.

Project description:In this study we used sequential catalysis-PPh(3)--catalyzed nucleophilic addition followed by Pd(0)-catalyzed Heck cyclization--to construct complex functionalized alkylidene phthalans rapidly, in high yields, and with good stereoselectivities (E/Z ratios of up to 1:22). The scope of this Michael-Heck reaction includes substrates bearing various substituents around the alkylidene phthalan backbone. Applying this efficient sequential catalysis, we accomplished concise total syntheses of 3-deoxyisoochacinic acid, isoochracinic acid, and isoochracinol.

| S-EPMC3391320 | biostudies-literature

Alcohol-assisted phosphine catalysis: one-step syntheses of dihydropyrones from aldehydes and allenoates.

Project description:This paper describes the phosphine-catalyzed annulation of methyl allenoate with various aromatic aldehydes to form 6-aryl-4-methoxy-5,6-dihydro-2-pyrones. In this reaction, the addition of an alcohol was necessary to induce dihydropyrone formation, with the optimal agent being methanol. Moreover, the addition of n-butyllithium suppressed the formation of the noncyclized product, leading to the exclusive isolation of the dihydropyrone. This method provides an efficient, one-step route toward disubstituted dihydropyrones from simple, stable starting materials.

| S-EPMC2532593 | biostudies-literature

Lewis Base-Bronsted Acid-Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses.

Project description:Establishing one-pot, multi-step protocols combining different types of catalysts is one important goal for increasing efficiency in modern organic synthesis. In particular, the high potential of biocatalysts still needs to be harvested. Based on an in-depth mechanistic investigation of a new organocatalytic protocol employing two catalysts {1,4-diazabicyclo[2.2.2]octane (DABCO); benzoic acid (BzOH)}, a sequence was established providing starting materials for enzymatic refinement (ene reductase; alcohol dehydrogenase): A gram-scale access to a variety of enantiopure key building blocks for natural product syntheses was enabled utilizing up to six catalytic steps within the same reaction vessel.

| S-EPMC8360128 | biostudies-literature

Stereoselective Syntheses of ?,?-Unsaturated ?-Amino Esters Through Phosphine-Catalyzed ?-Umpolung Additions of Sulfonamides to ?-Substituted Allenoates.

Project description:?,?-Unsaturated ?-amino esters can be synthesized efficiently and stereoselectively through phosphine-catalyzed ?-umpolung additions of sulfonamides to ?-substituted allenoates. The structures of the sulfonamide and ?-substituted allenoate partners can be varied to achieve a range of ?,?-unsaturated ?-amino esters with potentially interesting chemical and biological properties.

| S-EPMC4450090 | biostudies-literature

Cobalt(II) chloride catalyzed one-pot synthesis of alpha-aminonitriles.

Project description:A simple and efficient method has been developed for the synthesis of alpha-aminonitriles by a one-pot three- component condensation of aldehydes, amines, and potassium cyanide in acetonitrile in the presence of a catalytic amount of CoCl2 at room temperature.

| S-EPMC1399456 | 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