Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Microwave-assisted multicomponent reaction in water leading to highly regioselective formation of benzo[f]azulen-1-ones.

ABSTRACT: Microwave-assisted three-component reaction has been established for the regioselective synthesis of benzo[f]azulen-1-ones. The reaction was performed in aqueous media under microwave irradiation by using readily available and inexpensive starting materials. A total of 38 examples were examined to show a broad substrate scope and good overall yields (70-89%). The present new synthesis shows attractive green chemistry characteristics, such as the use of water as reaction media, concise one-pot conditions, short reaction periods (7-24 min), easy work-up/purification and reduced waste production without the use of any strong acids or metal promoters.

SUBMITTER: Wang SL

PROVIDER: S-EPMC3124679 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Microwave-assisted multicomponent reaction in water leading to highly regioselective formation of benzo[f]azulen-1-ones.

Wang Shu-Liang SL Cheng Chuang C Wu Fei-Yue FY Jiang Bo B Shi Feng F Tu Shu-Jiang SJ Rajale Trideep T Li Guigen G

Tetrahedron 20110601 25

Microwave-assisted three-component reaction has been established for the regioselective synthesis of benzo[f]azulen-1-ones. The reaction was performed in aqueous media under microwave irradiation by using readily available and inexpensive starting materials. A total of 38 examples were examined to show a broad substrate scope and good overall yields (70-89%). The present new synthesis shows attractive green chemistry characteristics, such as the use of water as reaction media, concise one-pot co ...[more]

PMID: 21731115

Similar Datasets

Microwave Assisted Selective Hydrolysis of Polyamides from Multicomponent Carpet Waste.

Project description:Selective hydrolysis of polyamide-6 (PA-6) and polyamide-66 (PA-66) from commercial multicomponent PA-6/PA-66/polypropylene (PP) carpet is demonstrated by a microwave-assisted acid catalyzed hydrothermal process, yielding monomeric products and solid polypropylene residue. First, an effective method is established to chemically recycle neat PA-6 and PA-66 granules using microwave irradiation. The optimized, hydrochloric acid (HCl) catalyzed process leads to selective production of monomers, 6-aminocaproic acid or adipic acid and hexamethylenediamine, after only 30 min. A piece of commercial carpet is then recycled using the same reaction conditions, but with the alteration of the reaction time from 1 to 6 h. The produced water-soluble products and the remaining solid residue are carefully characterized, proving that the polyamide-part of the carpet is selectively hydrolyzed into water-soluble monomers and the polypropylene-part remains as an unconverted solid that can be further used to produce recycled filaments containing the carpet residue and virgin polypropylene. The developed process opens the possibility to recycle multicomponent materials, such as carpets, through selective hydrolysis. It can also contribute to a circular economy, producing original monomers and materials ready for a new life-cycle.

| S-EPMC8272014 | biostudies-literature

Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles.

Project description:A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide-internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.

| S-EPMC3596043 | biostudies-other

Phosphine-Catalyzed α-Umpolung-Aldol Reaction for the Synthesis of Benzo[ b]azapin-3-ones.

Project description:A novel phosphine-catalyzed intermolecular cyclization between 2-sulfonamidobenzaldehyes and ynones is reported. This methodology serves as a conduit for the construction of benzo[ b]azepin-3-ones in good to excellent yields under mild conditions. The resulting 2-benzylidene moieties are formed exclusively in the E-configuration. Mechanistically, this unusual annulation occurs through a phosphine-catalyzed α-umpolung addition, followed by an aldol reaction. One of the benzo[ b]azepin-3-one products was converted to the core structure of 3-amino-[ a]benzazepin-2-one-1-alkanoic acids, many of which function as angiotensin-converting enzyme inhibitors.

| S-EPMC7338222 | biostudies-literature

Microwave-assisted xylanase reaction: impact in the production of prebiotic xylooligosaccharides.

Project description:The enzymatic production of prebiotic xylooligosaccharides (XOS) has become an attractive way to valorise lignocellulosic biomass. However, despite numerous xylanases reported for potential use in the production of XOS, most of the family GH10 also produce xylose. This monosaccharide can negatively affect the selectivity to stimulate the growth of intestinal microorganisms beneficial to human health. In this work, thermostable alkali-tolerant xylanase (BhXyn10A) from Bacillus halodurans S7 has been used to produce XOS under conventional convective heat transfer and microwave radiation. The microwave-assisted reaction markedly decreases the xylose content in the hydrolysates and significantly increases the yield of XOS, compared to conventional heating. Molecular dynamics simulations of BhXyn10A have shown increased fluctuations of the amino acids of the aglycone subsites suggesting that these subsites can determine the production of xylose. Thus, microwave heating could affect the amino acid fluctuations in the aglycone subsites reducing the xylose formation. These findings open up new avenues in enzyme technology for the production of XOS.

| S-EPMC8696575 | biostudies-literature

Highly diastereoselective synthesis of modified nucleosides via an asymmetric multicomponent reaction.

Project description:We have developed a practical synthesis of unique nucleoside derivatives via TiCl(4) promoted multicomponent reaction of optically active dihydrofuran, ethyl pyruvate/glyoxylate, and a TMS protected nucleobase in a single-pot operation.

| S-EPMC6037177 | biostudies-literature

A Microwave-Assisted Boudouard Reaction: A Highly Effective Reduction of the Greenhouse Gas CO2 to Useful CO Feedstock with Semi-Coke.

Project description:The conversion of CO2 into more synthetically flexible CO is an effective and potential method for CO2 remediation, utilization and carbon emission reduction. In this paper, the reaction of carbon-carbon dioxide (the Boudouard reaction) was performed in a microwave fixed bed reactor using semi-coke (SC) as both the microwave absorber and reactant and was systematically compared with that heated in a conventional thermal field. The effects of the heating source, SC particle size, CO2 flow rate and additives on CO2 conversion and CO output were investigated. By microwave heating (MWH), CO2 conversion reached more than 99% while by conventional heating (CH), the maximum conversion of CO2 was approximately 29% at 900 °C. Meanwhile, for the reaction with 5 wt% barium carbonate added as a promoter, the reaction temperature was significantly reduced to 750 °C with an almost quantitative conversion of CO2. Further kinetic calculations showed that the apparent activation energy of the reaction under microwave heating was 46.3 kJ/mol, which was only one-third of that observed under conventional heating. The microwave-assisted Boudouard reaction with catalytic barium carbonate is a promising method for carbon dioxide utilization.

| S-EPMC8001657 | biostudies-literature

Rapid and efficient microwave-assisted synthesis of highly sulfated organic scaffolds.

Project description:Sulfation of multiply hydroxylated small organic molecules is fraught with problems of poor yield, multitude of products and long reaction times. We have developed a rapid microwave-based method for synthesis of highly sulfated small organic molecules, which affords the per-sulfated product in moderate to excellent yields and high purity. The method is expected to be of value in the discovery of per-sulfated organic molecules as mimics of glycosaminoglycans, which are being increasingly recognized as modulators of key physiological functions.

| S-EPMC2084256 | biostudies-literature

Microwave-Assisted Kabachnik⁻Fields Reaction with Amino Alcohols as the Amine Component.

Project description:In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik-Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-α-aminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified. N,N-Bis(phosphinoylmethyl)amines containing a hydroxyethyl group were also prepared by the double Kabachnik-Fields reaction of ethanolamine with an excess of paraformaldehyde and secondary phosphine oxides. The crystal structure of a 2-hydroxyethyl-α-aminophosphine oxide and a bis(phosphinoylmethyl)ethanolamine was studied by X-ray analysis.

| S-EPMC6514811 | biostudies-literature

Free MoS2 Nanoflowers Grown on Graphene by Microwave-Assisted Synthesis as Highly Efficient Non-Noble-Metal Electrocatalysts for the Hydrogen Evolution Reaction.

Project description:Advanced approaches to preparing non-noble-metal electrocatalysts for the hydrogen evolution reaction (HER) are considered to be a significant breakthrough in promoting the exploration of renewable resources. In this work, a hybrid material of MoS2 nanoflowers (NFs) on reduced graphene oxide (rGO) was synthesized as a HER catalyst via an environmentally friendly, efficient approach that is also suitable for mass production. Small-sized MoS2 NFs with a diameter of ca. 190 nm and an abundance of exposed edges were prepared by a hydrothermal method and were subsequently supported on rGO by microwave-assisted synthesis. The results show that MoS2 NFs were distributed uniformly on the remarkably reduced GO and preserved the outstanding original structural features perfectly. Electrochemical tests show that the as-prepared hybrid material exhibited excellent HER activity, with a small Tafel slope of 80 mV/decade and a low overpotential of 170 mV.

| S-EPMC4996486 | biostudies-literature

Direct Synthesis of the Phenanthroviridone Skeleton Using a Highly Regioselective Nitroquinone Diels-Alder Reaction.

Project description:A variety of nucleophiles react efficiently with in situ generated nitroquinones. The reaction with substituted resorcinols led to the direct synthesis of the phenanthroviridinone and lagumycin skeleton via a highly regioselective Diels-Alder reaction.

| S-EPMC7191567 | 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