Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization.

ABSTRACT: We developed an efficient synthesis of aza-chromones from 3-iodo-4-(1H)-pyridones and terminal acetylenes via a cascade carbonylation-Sonogashira-cyclization reaction. By controlling the use of bases, both 6-aza-chromones 5 and 3-(4-oxo-1,4-dihydroquinoline-3-carbonyl)-4H-pyrano[3,2-c]quinolin-4-ones 6 could be selectively obtained in moderate to good yields.

SUBMITTER: Cheng G

PROVIDER: S-EPMC5493695 | biostudies-other | 2017 Jun

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization.

Cheng Gang G Qi Yingbei Y Zhou Xiaoqian X Sheng Rong R Hu Yong-Zhou YZ Hu Youhong Y

Scientific reports 20170630 1

We developed an efficient synthesis of aza-chromones from 3-iodo-4-(1H)-pyridones and terminal acetylenes via a cascade carbonylation-Sonogashira-cyclization reaction. By controlling the use of bases, both 6-aza-chromones 5 and 3-(4-oxo-1,4-dihydroquinoline-3-carbonyl)-4H-pyrano[3,2-c]quinolin-4-ones 6 could be selectively obtained in moderate to good yields. ...[more]

PMID: 28667287

Similar Datasets

A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives.

Project description:A versatile synthetic procedure is described to prepare the benzimidazole-fused 1,2,4-thiadiazoles 2a-c via a methanesulfonyl chloride initiated multistep cyclization involving the intramolecular reaction of an in-situ generated carbodiimide with a thiourea unit. The structure of the intricate heterocycle 2a was confirmed by single-crystal X-ray analysis and its mechanism of formation supported by DFT computations.

| S-EPMC4311674 | biostudies-literature

Acid/Base-Steered Cascade Cyclization: An Efficient One-Pot Access to Diverse Isobenzofuranone and Isoindolobenzoxazinone Derivatives.

Project description:We herein report the acid/base-steered two distinct reaction pathways of 2-acylbenzoic acids with isatoic anhydrides. In the presence of Na2CO3, the cascade process consists of the cyclization of 2-acetylbenzoic acid and nucleophilic ring-opening reaction of isatoic anhydride to furnish isobenzofuranone derivatives with high efficiency. However, p-toluenesulfonic acid can promote the product isobenzofuranones to undergo sequential intramolecular rearrangment, nucleophilic addition and cyclization reaction to produce diverse isoindolobenzoxazinones in good yields. The synthetic utility of this method was further demonstrated by the gram-scale preparation of the desired products and the facile transformations of the resulting products.

| S-EPMC9921644 | biostudies-literature

Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction.

Project description:A low loading of a quinine-derived squaramide efficiently catalyzes the triple-domino Michael/aza-Henry/cyclization reaction between 1,3-dicarbonyl compounds, ?-nitroolefins, and aldimines to provide tetrahydropyridines bearing three contiguous stereogenic centers in good yields, excellent enantiomeric excesses, and up to high diastereomeric ratios.

| S-EPMC4611353 | biostudies-literature

Synthesis of Indolines and Derivatives by Aza-Heck Cyclization.

Project description:For the first time, an aza-Heck cyclization that allows the preparation of indoline scaffolds is described. Using N-hydroxy anilines as electrophiles, which can be easily accessed from the corresponding nitroarenes, this method provides indolines bearing pendant functionality and complex ring topologies. Synthesis of challenging indolines, such as those bearing fully substituted carbon atoms at C2, is also possible using this method.

| S-EPMC6750995 | biostudies-literature

One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines.

Project description:An operationally simple, one-pot, two-step cascade method has been developed to afford quinazolino[1,2,3]triazolo[1,4]benzodiazepines. This unique, atom-economical transformation engages five reactive centers (amide, aniline, carbonyl, azide, and alkyne) and employs environmentally benign iodine as a catalyst. The method proceeds via sequential quinazolinone-forming condensation and intramolecular azide-alkyne 1,3-dipolar cycloaddition reactions. Substrate scope, multicomponent examples, and mechanistic insights are discussed.

| S-EPMC3486955 | biostudies-literature

One-pot synthesis of fused pyrroles through a key gold-catalysis-triggered cascade.

Project description:A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields.

| S-EPMC4098939 | biostudies-literature

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger-aza-Wittig reaction.

Project description:A fast and efficient protocol for the synthesis of N,N'-disubstituted urea derivatives from alkyl halides and primary or secondary amines has been developed. The synthetic pathway combines nucleophilic substitutions and a Staudinger-aza-Wittig reaction in the presence of polymer-bound diphenylphosphine under 14 bar of CO2 pressure and has been performed in a one-pot two-step process. The protocol has been optimized under microwave irradiation and the scale-up experiment has been conducted under conventional conditions in a Parr reactor. The final compounds were isolated after simple filtration in almost quantitative overall yields which makes this procedure facile and rapid to execute.

| S-EPMC3869261 | biostudies-literature

One-Pot Synthesis of Seven-Membered Heterocyclic Derivatives of Diazepines Involving Copper-Catalyzed Rearrangement Cascade Allyl-Amination.

Project description:A novel and efficient method has been proposed for the synthesis of 1,4-benzodiazepine-5-ones from o-nitrobenzoic N-allylamides by using molybdenyl acetylacetonate and copper(II) trifluoromethanesulfonate as catalysts in the presence of triphenylphosphine. This synthesis process involves nitrene formation, C-H bond insertion, C═C bond rearrangement, and C-N bond formation cascade reactions via copper- and molybdenum-catalyzed mediation. The method features a wide substrate scope and a moderate to high yield (up to 90%), exhibiting the possibility for practical applications.

| S-EPMC8567460 | biostudies-literature

One-Pot Synthesis of α-Alkyl Styrene Derivatives.

Project description:There is a significant need to develop more rapid and efficient routes to styrene derivatives, since they are extensively used in polymer sciences. This manuscript reports a one-pot synthesis of an array of α-alkyl styrene derivatives from readily available natural products (i.e., estragole and safrole). This method is regioselective, producing a rearranged adduct, under transition metal-free conditions. This methodology has broad nucleophile scope, even tolerating sterically hindered nucleophiles; it is general for carbon, nitrogen, oxygen, and sulfur nucleophiles.

| S-EPMC8359136 | biostudies-literature

Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction.

Project description:A facile microwave-assisted method for the synthesis of tetramic acid derivatives has been developed through an Ugi/Dieckmann cyclization strategy with DBU. This two-step one-pot procedure afforded the targeted tetramic acid analogues in good yields. With commercially available Ugi starting materials, microwave irradiation, a simple operation, excellent yields, and a broad scope, this reaction has the potential to produce a large number of tetramic acid analogues, which cannot be easily accessed by the classic synthetic methods.

| S-EPMC7155898 | 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