Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Open vessel mode microwave-assisted synthesis of 2-oxazolines from carboxylic acids.

ABSTRACT: Microwave-assisted synthesis of 2-oxazolines from carboxylic acids using the open vessel technique is described. This efficient method involves direct condensation of carboxylic acids with excess 2-amino-2-methyl-1-propanol at 170 °C to give the corresponding 2-oxazolines in moderate to excellent yields.

SUBMITTER: Sharma R

PROVIDER: S-EPMC3083025 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Open vessel mode microwave-assisted synthesis of 2-oxazolines from carboxylic acids.

Sharma Rishi R Vadivel Subramanian K SK Duclos Richard I RI Makriyannis Alexandros A

Tetrahedron letters 20091001 42

Microwave-assisted synthesis of 2-oxazolines from carboxylic acids using the open vessel technique is described. This efficient method involves direct condensation of carboxylic acids with excess 2-amino-2-methyl-1-propanol at 170 °C to give the corresponding 2-oxazolines in moderate to excellent yields. ...[more]

PMID: 21533007

Similar Datasets

Microwave-Assisted Catalytic Method for a Green Synthesis of Amides Directly from Amines and Carboxylic Acids.

Project description:Amide bonds are among the most interesting and abundant molecules of life and products of the chemical pharmaceutical industry. In this work, we describe a method of the direct synthesis of amides from carboxylic acids and amines under solvent-free conditions using minute quantities of ceric ammonium nitrate (CAN) as a catalyst. The reactions are carried out in an open microwave reactor and allow the corresponding amides to be obtained in a fast and effective manner when compared to other procedures of the direct synthesis of amides from acids and amines reported so far in the literature. The amide product isolation procedure is simple, environmentally friendly, and is performed with no need for chromatographic purification of secondary amides due to high yields. In this report, primary amines were used in most examples. However, the developed procedure seems to be applicable for secondary amines as well. The methodology produces a limited amount of wastes, and a catalyst can be easily separated. This highly efficient, robust, rapid, solvent-free, and additional reagent-free method provides a major advancement in the development of an ideal green protocol for amide bond formation.

| S-EPMC7221698 | biostudies-literature

A Facile Microwave-Assisted Synthesis of Oxazoles and Diastereoselective Oxazolines Using Aryl-Aldehydes, <i>p</i>-Toluenesulfonylmethyl Isocyanide under Controlled Basic Conditions.

Project description:In this study, a highly efficient two-component [3 + 2] cycloaddition reaction of substituted aryl aldehydes with 4-toluenesulfonylmethyl isocyanide (TosMIC) in the presence of 2 equiv of potassium phosphate as a base to 5-substituted oxazoles were established in a isopropanol medium under microwave irradiation. However, using 1 equiv of K3PO4 as a base resulted in the diastereoselective synthesis of 4,5-disubstituted oxazolines under identical reaction conditions. The foremost benefits of these protocols are the moderate-to-excellent yields with good functional group compatibility, simple experimental procedure, inexpensive readily available starting materials, nonchromatographic purification, and high bond-forming efficiency. The synthetic manipulation reported herein represents a cleaner route to the sustainable preparation of 5-substituted oxazoles and diastereoselective 4,5-disubstituted oxazolines derivatives.

| S-EPMC7643254 | biostudies-literature

Microwave-Assisted Knoevenagel-Doebner Reaction: An Efficient Method for Naturally Occurring Phenolic Acids Synthesis.

Project description:The common chemical method to synthesize Phenolic Acids (PAs) involves a relatively considerable energy intake. In order to solve this issue, microwave-assisted Knoevenagel-Doebner condensations were developed. Nevertheless, these synthetic procedures prove difficult to reproduce. Herein, we developed and optimized-by using a combination of a Design of Experiment and a standard optimization approach-a reliable procedure that converts naturally occuring p-hydroxybenzaldehydes into the corresponding PAs with conversions of 86-99% and in 85-97% yields.

| S-EPMC6156279 | biostudies-literature

Microwave-Assisted Synthesis of N-Phenylsuccinimide.

Project description:A microwave-assisted synthesis of N-phenylsuccinimide has been developed for the second-semester organic teaching laboratory. Utilizing this procedure, N-phenylsuccinimide can be synthesized by heating a mixture of aniline and succinic anhydride in a domestic microwave oven for four minutes in moderate yields (40-60%). This technique reduces the reaction time as compared to the traditional synthesis by several hours, which allows the preparation to be achieved in a single organic chemistry laboratory period. This reaction is performed in the absence of solvent, is energy efficient, and is atom economical; therefore, it represents a "greener" preparation than the traditional synthesis of N-phenylsuccinimide.

| S-EPMC3224042 | biostudies-literature

Microwave-assisted synthesis of rhodamine derivatives.

Project description:The microwave synthesis of 12 rhodamine-derived imines is described. The present work involves condensation of rhodamine hydrazide with various aromatic aldehydes in ethanol under microwave irradiation. The results obtained indicate that, unlike classical heating, microwave irradiation results in higher yields, shorter reaction time, mild reaction condition and simple work-up procedure. The structures of synthesized compounds were confirmed by 1H-NMR, 13C-NMR, FT-IR and high-resolution mass spectra data.

| S-EPMC7082095 | biostudies-literature

Microwave assisted synthesis of bridgehead alkenes.

Project description:A new, concise method to synthesize triene precursors for the type 2 intramolecular Diels-Alder reaction has been developed. Microwave irradiation of the trienes provides a convenient method for the synthesis of bridgehead alkenes. Higher yields, shorter reaction times, and lower reaction temperatures provide a general and efficient route to this interesting class of molecules.

| S-EPMC3064725 | biostudies-literature

An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids.

Project description:Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis-Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5-chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 ?M) and may represent a novel hit for further SAR studies and antiviral improvement.

| S-EPMC7125588 | biostudies-literature

Microwave assisted synthesis of Py-Im polyamides.

Project description:Microwave synthesis was utilized to rapidly build Py-Im polyamides in high yields and purity using Boc-protection chemistry on Kaiser oxime resin. A representative polyamide targeting the 5'-WGWWCW-3' (W = A or T) subset of the consensus Androgen and Glucocorticoid Response Elements was synthesized in 56% yield after 20 linear steps and HPLC purification. It was confirmed by Mosher amide derivatization of the polyamide that a chiral ?-amino acid does not racemize after several additional coupling steps.

| S-EPMC3365540 | biostudies-literature

Microwave assisted synthesis of triazoloquinazolinones and benzimidazoquinazolinones.

Project description:BackgroundBenzimidazoquinazolinones and related quinazolines are classes of heterocycles that are of considerable interest because of the diverse range of their biological properties. Although numerous classes of quinazolines have been conventionally synthesized, their syntheses have been suffered due to the multiple steps that sometimes have described in their preparation and also their chemical transformations that have been taken hours or even days to be completed. However, microwave energy can offer numerous benefits for performing synthesis of organic compounds including reduced pollution, increased reaction rates, yield enhancements, and cleaner chemistries.ResultsSynthesis of a series of triazoloquinazolinones and benzimidazoquinazolinones has been achieved under microwave irradiation. The products were obtained in nearly quantitative yields within few minutes during the reaction of aromatic aldehydes with 5-amino-1(H)-1,2,4-triazole (or 2-aminobenzimidazole) and dimedone in DMF.ConclusionMicrowave irradiation can be used as a facile and general method for the construction of a wide variety of triazoloquinazolinones and benzimidazoquinazolinones. The reaction involves a three component condensation (with potential for combinatorial work) being carried out with almost productive yields by microwave irradiation and considerably shortened reaction time.

| S-EPMC1847824 | biostudies-literature

Hydrocarbon Synthesis via Photoenzymatic Decarboxylation of Carboxylic Acids.

Project description:A recently discovered photodecarboxylase from Chlorella variabilis NC64A ( CvFAP) bears the promise for the efficient and selective synthesis of hydrocarbons from carboxylic acids. CvFAP, however, exhibits a clear preference for long-chain fatty acids thereby limiting its broad applicability. In this contribution, we demonstrate that the decoy molecule approach enables conversion of a broad range of carboxylic acids by filling up the vacant substrate access channel of the photodecarboxylase. These results not only demonstrate a practical application of a unique, photoactivated enzyme but also pave the way to selective production of short-chain alkanes from waste carboxylic acids under mild reaction conditions.

| S-EPMC6385076 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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