Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products.

ABSTRACT: Various N-propargylpyrrole and indolecarboxylic acids were efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.

SUBMITTER: Taskaya S

PROVIDER: S-EPMC4464457 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products.

Taskaya Sultan S Menges Nurettin N Balci Metin M

Beilstein journal of organic chemistry 20150528

Various N-propargylpyrrole and indolecarboxylic acids were efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions. ...[more]

PMID: 26124892

Similar Datasets

3-Phenyl-1H-pyrrolo[2,1-c][1,4]oxazin-1-one.

Project description:The mol-ecule of the title compound, C(13)H(9)NO(2), is slightly twisted with a dihedral angle of 4.85?(9)° between the nine-membered ring system and the phenyl ring. The nine non-H atoms of the 1H-pyrrolo[2,1-c][1,4]oxazin-1-one system are coplanar [r.m.s. deviation = 0.0122?(2)?Å]. In the crystal, weak inter-molecular C-H?O inter-actions link mol-ecules into chains along [10]. The crystal studied was an inversion twin with a 0.48624?(9):0.51376?(9) domain ratio.

| S-EPMC2979495 | biostudies-literature

3-Methyl-1H-pyrrolo[2,1-c][1,4]oxazin-1-one.

Project description:In the title mol-ecule, C(8)H(7)NO(2), all the non-H atoms lie essentially in the same plane (r.m.s. deviation = 0.019?Å) In the crystal structure, weak inter-molecular C-H?O inter-actions link mol-ecules into chains along [100]. In addition, there are ?-? stacking inter-actions between mol-ecules related by the c-glide plane, with alternating centroid-centroid distances of 3.434?(2) and 3.639?(2)?Å.

| S-EPMC2983595 | biostudies-literature

8-Phenyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo-[2,1-c][1,4]oxazin-6-one.

Project description:In the title compound, C(13)H(15)NO(2), the hexa-hydro-pyrrolo-[2,1-c][1,4]oxazine fragment is disordered over two conformations (A and B) in a 0.656?(5):0.344?(5) ratio. The five-membered ring is similarly disordered and adopts an envelope conformation in A, while in B this ring is nearly planar [maximum deviation = 0.088?(1)?Å]. The six-membered rings in both A and B exhibit chair conformations. In the crystal, weak inter-molecular C-H?O hydrogen bonds link the mol-ecules into ribbons propagating in [010].

| S-EPMC3200730 | biostudies-literature

1,3-Oxazin-6-one Derivatives and Bohemamine-Type Pyrrolizidine Alkaloids from a Marine-Derived Streptomyces spinoverrucosus.

Project description:Two new 1,3-oxazin-6-one derivatives (1 and 2) and six new bohemamine-type pyrrolizidine alkaloids (3-8) were isolated from the marine-derived Streptomyces spinoverrucosus strain SNB-048. Their structures including the absolute configurations were fully elucidated on the basis of spectroscopic analysis, ECD spectra, quantum chemical calculations, and chemical methods. Compounds 1 and 2 possess a γ-lactam moiety and a 1,3-oxazin-6-one system.

| S-EPMC5435457 | biostudies-literature

Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones.

Project description:A combined experimental and computational study on regioselective gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out.

| S-EPMC3678844 | biostudies-literature

Gold-catalyzed cyclization of allenyl acetal derivatives.

Project description:The gold-catalyzed transformation of allenyl acetals into 5-alkylidenecyclopent-2-en-1-ones is described. The outcome of our deuterium labeling experiments supports a 1,4-hydride shift of the resulting allyl cationic intermediates because a complete deuterium transfer is observed. We tested the reaction on various acetal substrates bearing a propargyl acetate, giving 4-methoxy-5-alkylidenecyclopent-2-en-1-ones 4 via a degradation of the acetate group at the allyl cation intermediate.

| S-EPMC3778408 | biostudies-literature

A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline.

Project description:A convenient CuI/L-proline-catalyzed, two-step one-pot method has been developed for the preparation of indolo[1,2-a]quinazoline derivatives using a sequential Ullmann-type C-C and C-N coupling. This protocol provides an operationally simple and rapid strategy for preparing indolo[1,2-a]quinazoline derivatives and displays good functional group tolerance. All the starting materials are commercial available or can be easily prepared.

| S-EPMC4222401 | biostudies-literature

Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes.

Project description:In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicyclic pyrrolo-fused pyridinones by a 6-exo-dig process, while the presence of a phenyl group at the C-C triple bond promotes the 7-endo-dig cyclization giving pyrrolo-azepines.

| S-EPMC3252845 | biostudies-literature

Gold(I)-Catalyzed Haloalkynylation of Aryl Alkynes: Two Pathways, One Goal.

Project description:Haloalkynylation reactions provide an efficient method for the simultaneous introduction of a halogen atom and an acetylenic unit. For the first time, we report a gold(I)-catalyzed haloalkynylation of aryl alkynes that delivers exclusively the cis addition product. This method enables the simple synthesis of conjugated and halogenated enynes in yields of up to 90 %. Notably, quantum chemical calculations reveal an exceptional interplay between the place of the attack at the chloroacetylene: No matter which C-C bond is formed, the same enyne product is always formed. This is only possible through rearrangement of the corresponding skeleton. Hereby, one reaction pathway proceeds via a chloronium ion with a subsequent aryl shift; in the second case the corresponding vinyl cation is stabilized by a 1,3-chlorine shift. 13 C-labeling experiments confirmed that the reaction proceeds through both reaction pathways.

| S-EPMC7318269 | biostudies-literature

Gold-catalyzed formal [4? + 2?]-cycloadditions of propiolate derivatives with unactivated nitriles.

Project description:Gold-catalyzed hetero-[4? + 2?]-cycloadditions of tert-butyl propiolates with unactivated nitriles are described; the resulting 6H-1,3-oxazin-6-ones are not easily accessible via conventional methods. This new finding enables a one-pot gold-catalyzed synthesis of highly substituted pyridines through sequential gold-catalyzed reactions of tert-butyl propiolates with nitriles, and then with electron-deficient alkynes in the same solvent. The utility of these [4 + 2]-cycloadditions is further expanded with various aldehydes, ketones and 2-phenyloxetane, yielding satisfactory yields of cycloadducts.

| S-EPMC5950837 | 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