Browse
Submit Data
Databases
API
Help

Dataset Information

21 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Gram-Scale Synthesis of a Bench-Stable 5,5?-Unsubstituted Terpyrrole.

ABSTRACT: The controlled preparation of higher order oligopyrrolic species holds broad utility across the chemical and material sciences. Here, we describe the gram-scale synthesis of a bench-stable 5,5?-unsubstituted terpyrrole in excellent yield via a tandem Suzuki cross-coupling with in situ deprotection. The solution and solid-state stability as well as UV-vis, fluorescence, and single crystal X-ray diffraction structure are also detailed.

SUBMITTER: Brewster JT

PROVIDER: S-EPMC6381930 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Gram-Scale Synthesis of a Bench-Stable 5,5″-Unsubstituted Terpyrrole.

Brewster James T JT Zafar Hadiqa H McVeigh Matthew M Wight Christopher D CD Anguera Gonzalo G Steinbrück Axel A Lynch Vincent M VM Sessler Jonathan L JL

The Journal of organic chemistry 20180703 16

The controlled preparation of higher order oligopyrrolic species holds broad utility across the chemical and material sciences. Here, we describe the gram-scale synthesis of a bench-stable 5,5″-unsubstituted terpyrrole in excellent yield via a tandem Suzuki cross-coupling with in situ deprotection. The solution and solid-state stability as well as UV-vis, fluorescence, and single crystal X-ray diffraction structure are also detailed. ...[more]

PMID: 29927588

Similar Datasets

Multi-gram scale synthesis of FR180204.

Project description:A concise synthesis of the ERK inhibitor FR180204 has been developed. The synthesis consists of six operationally simple steps and can be utilized to make multi-gram quantities of FR180204.

| S-EPMC2862695 | biostudies-literature

Synthesis of Functionalized 1,3,2-Benzodiazaborole Cores Using Bench-Stable Components.

Project description:The azaborine motif provides a unique opportunity to develop core isosteres by inserting B-N units in place of C═C bonds within aromatic scaffolds, creating new pseudoaromatic building blocks that retain comparable structural features. Previous synthetic routes to the 1,3,2-benzodiazaborole core have used organoboron dichlorides and boronic acids as the boron precursors. The transformation developed herein utilizes entirely bench stable starting materials, including organotrifluoroborates, enabling a wider array of substrate analogues under facile reaction conditions. Furthermore, physical, structural, and electronic properties of these compounds were explored computationally to understand the influence of the B-N replacement on the structure, aromaticity, and isosteric viability of these analogues.

| S-EPMC4862404 | biostudies-literature

Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.

Project description:A reasonable synthesis design by strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (-)-zephyranthine. The concise route includes a catalytic Michael/Michael cascade for the asymmetric synthesis of a penta-substituted cyclohexane with three contiguous stereogenic centers, a remarkable 8-step one-pot operation to easily assemble the zephyranthine tetracyclic skeleton, the regioselective construction of a double bond in the C ring and an asymmetric dihydroxylation. This synthesis is also flexible and paves a potential path to a variety of cyclohexylamine-fused tricyclic or polycyclic alkaloids.

| S-EPMC8278928 | biostudies-literature

Synthesis of Highly Functionalizable Symmetrically and Unsymmetrically Substituted Triarylboranes from Bench-Stable Boron Precursors.

Project description:A novel and convenient methodology for the one-pot synthesis of sterically congested triarylboranes by using bench-stable aryltrifluoroborates as the boron source is reported. This procedure gives systematic access to symmetrically and unsymmetrically substituted triarylboranes of the types BAr2 Ar' and BArAr'Ar'', respectively. Three unsymmetrically substituted triarylboranes as well as their iridium-catalyzed C-H borylation products are reported. These borylated triarylboranes contain one to three positions that can subsequently be orthogonally functionalized in follow-up reactions, such as Suzuki-Miyaura cross-couplings or Sonogashira couplings.

| S-EPMC8360097 | biostudies-literature

Gram-scale synthesis of the A'B'-subunit of angelmicin B.

Project description:A gram-scale enantiospecific synthesis of the A'B'-subunit of angelmicin B is reported. The synthesis involves a Lewis acid catalyzed contrasteric Diels-Alder reaction and a tandem silyl zincate 1,6-addition/enolate oxidation sequence.

| S-EPMC3237735 | biostudies-literature

One-Pot Gram-Scale Synthesis of Hydrogen-Terminated Silicon Nanoparticles.

Project description:Silicon nanoparticles (Si NPs) are highly attractive materials for typical quantum dots functions, such as in light-emitting and bioimaging applications, owing to silicon's intrinsic merits of minimal toxicity, low cost, high abundance, and easy and highly stable functionalization. Especially nonoxidized Si NPs with a covalently bound coating serve well in these respects, given the minimization of surface defects upon hydrosilylation of H-terminated Si NPs. However, to date, methods to obtain such H-terminated Si NPs are still not easy. Herein, we report a new synthetic method to produce size-tunable robust, highly crystalline H-terminated Si NPs (4-9 nm) using microwave irradiation within 5 min at temperatures between 25 and 200 °C and their further covalent functionalization. The key step to obtain highly fluorescent (quantum yield of 7-16%) green-red Si NPs in one simple step is the reduction of triethoxysilane and (+)-sodium l-ascorbate, yielding routinely ∼1 g of H-Si NPs via a highly scalable route in 5-15 min. Subsequent functionalization via hydrosilylation yielded Si NPs with an emission quantum yield of 12-14%. This approach can be used to easily produce high-quality H-Si NPs in gram-scale quantities, which brings the application of functionalized Si NPs significantly closer.

| S-EPMC6160286 | biostudies-literature

Gram-Scale Synthesis of a β-Secretase 1 (BACE 1) Inhibitor.

Project description:Development of a scalable synthesis of an oxazine class of β-secretase inhibitor is described. Trifluoromethylated acyloin synthesis by the reaction of a mandelic acid with trifluoroacetic anhydride in the presence of pyridine (Dakin-West reaction) was used as an efficient strategy to install the key trifluoromethyl substituent on the oxazine ring. Diastereoselective addition of methyl magnesium bromide to a cyclic sulfamidate imine and trimethylsilyl trifluoromethanesulfonate catalyzed intramolecular amidine formation to yield oxazine-3-amine are some of the significant, novel synthetic methods developed in this synthesis. These critical transformations allowed a concise 11-step route to the target compound with excellent overall yields.

| S-EPMC6044763 | biostudies-literature

Gram-Scale Synthesis of 1,8-Naphthyridines in Water: The Friedlander Reaction Revisited.

Project description:The products of the Friedlander reaction, i.e., 1,8-naphthyridines, have far-reaching impacts in materials science, chemical biology, and medicine. The reported synthetic methodologies elegantly orchestrate the diverse synthetic routes of naphthyridines but require harsh reaction conditions, organic solvents, and expensive metal catalysts. Here, we introduce gram-scale synthesis of 1,8-naphthyridines in water using an inexpensive and biocompatible ionic liquid (IL) as a catalyst. This is the first-ever report on the synthesis of naphthyridines in water. This is a one-step reaction, and the product separation is relatively easy. The choline hydroxide (ChOH) is used as a metal-free, nontoxic, and water-soluble catalyst. In comparison to other catalysts reported in the literature, ChOH has the advantage of forming an additional hydrogen bond with the reactants, which is the vital step for the reaction to happen in water. Density functional theory (DFT) and noncovalent interaction (NCI) plot index analysis provide the plausible reaction mechanism for the catalytic cycle and confirm that hydrogen bonds with the IL catalyst are pivotal to facilitate the reaction. Molecular docking and molecular dynamics (MD) simulations are also performed to demonstrate the potentialities of the newly synthesized products as drugs. Through MD simulations, it was established that the tetrahydropyrido derivative of naphthyridine (10j) binds to the active sites of the ts3 human serotonin transporter (hSERT) (PDB ID: 6AWO) without perturbing the secondary structure, suggesting that 10j can be a potential preclinical drug candidate for hSERT inhibition and depression treatment.

| S-EPMC8320145 | biostudies-literature

Gram-Scale Domino Synthesis in Batch and Flow Mode of Azetidinium Salts.

Project description:Azetidinium salts are important motifs in organic synthesis but are difficult to obtain due to extremely long synthetic protocols. Herein, a rapid continuous-flow process for the on-demand synthesis of azetidinium salts is described. In particular, the nucleophilic addition of secondary amines and the subsequent intramolecular N-cyclization have been investigated in batch and continuous-flow modes, exploring the effects of solvent type, temperature, reaction time, and amine substituent on the synthesis of azetidinium salts. This has enabled us to quickly identify optimal reaction conditions and obtain microkinetic parameters, verifying that the use of a flow reactor leads to a reduction of the activation energy for the epichlorohydrin aminolysis due to the better control of mass and heat transfer during reaction. This confirms the key role of continuous-flow technologies to affect the kinetics of a reaction and make synthetic protocols ultrarapid and more efficient.

| S-EPMC8524416 | biostudies-literature

Gram-Scale Synthesis and Supramolecular Complex of Precursors of Clar's Hydrocarbon Triangulene.

Project description:We present to date the most efficient gram-scale synthesis of triangulene-4,8-dione and 12-hydroxytriangulene-4,8-dione, the precursors of Clar's hydrocarbon, in overall yields >50%. The direct dihydroprecursors of triangulene, obtained upon reduction of triangulene-4,8-dione, were stabilized in a supramolecular complex with a tetracationic cyclophane ExBox4+ and characterized by single-crystal X-ray crystallography. This result represents the first step in an endeavor to stabilize the fragile core of triangulene in an inclusion complex in solution and solid state.

| S-EPMC6737831 | 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