Browse
Submit Data
Databases
API
Help

Dataset Information

12 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation.

ABSTRACT: The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and N-substituted maleimide in stereoselective fashion.

SUBMITTER: Zhang X

PROVIDER: S-EPMC5082442 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation.

Zhang Xiaofeng X Pham Kenny K Liu Shuai S Legris Marc M Muthengi Alex A Jasinski Jerry P JP Zhang Wei W

Beilstein journal of organic chemistry 20161018

The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and <i>N</i>-substituted maleimide in stereoselective fashion. ...[more]

PMID: 27829928

Similar Datasets

One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation.

Project description:A novel dicyclopenta-fused peropyrene derivative 1 was synthesized via a palladium-catalyzed four-fold alkyne annulation of 1,3,6,8-tetrabromo-2,7-diphenylpyrene (5) with diphenylacetylene. The annulative π-extension reaction toward 1 involved a twofold [3 + 2] cyclopentannulation and subsequent twofold [4 + 2] benzannulation. The structure of 1 is unambiguously confirmed by X-ray crystallography; 1 adopted a twisted geometry due to the steric hindrance of the phenyl rings and the hydrogen substituents at the bay regions. Notably, compound 1 exhibits a narrow energy gap (1.78 eV) and a lower LUMO energy level than the parent peropyrene without the fusion of the five-membered rings. In addition, the effects of the peri-fused pentagons on the aromaticity and molecular orbitals of 1 were evaluated by theoretical calculations. This work presents an efficient method to develop π-extended aromatic hydrocarbons with cyclopenta moieties.

| S-EPMC7188986 | biostudies-literature

Stereoselective one-pot synthesis of polypropionates.

Project description:Polypropionates-motifs with alternating methyl and hydroxy groups-are important segments of many natural products possessing high bioactivity and therapeutic value. Synthetic access to these structures remains an area of intensive interest, focusing on the establishment of the contiguous stereocentres and a desire for operational simplicity. Here we report an efficient strategy for the stereoselective assembly of polypropionates with three or four stereocentres through a three-step relay process that include Diels-Alder reaction, silylenol ether hydrolysis and Baeyer-Villiger oxidation. The stereochemistry and functionality of the resulting polypropionates depend on the substitution pattern of the diene and dienophile substrates of the Diels-Alder cycloaddition. More importantly, the relay sequence is effectively performed in one pot, and the product could potentially undergo the same sequence for further elaboration. Finally, the C1-C9 segment of the macrolide etnangien is constructed with four of the six stereogenic centres established using the relay sequence.Polypropionates are present in many natural products possessing high bioactivity and therapeutic value. Here the authors show a strategy for the stereoselective assembly of polypropionates with three or four stereocentres through a process that includes a Diels-Alder reaction, silylenol ether hydrolysis and Baeyer-Villiger oxidation.

| S-EPMC5612996 | biostudies-literature

One-Pot, Highly Stereoselective Synthesis of Dithioacetal-?,?-Diglycosides.

Project description:A one-step access to dithioacetal-?,?-diglycosides is reported. The synthetic strategy is based on the thioacetalization of aldehydes or ketones via highly stereoselective ring-opening of 1,6 anhydrosugars with bis(trimethylsilyl)sulfide.

| S-EPMC6017313 | biostudies-literature

Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3'-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction.

Project description:Described herein is the development of a facile and efficient methodology for the synthesis of novel turmerone motif-fused 3,3'-pyrrolidinyl-dispirooxindoles 3-5 via a multicomponent 1,3-dipolar cycloaddition of dienones 2 with azomethine ylides (thermally generated in situfrom isatins and proline or thioproline or sarcosine). Products bearing four or three consecutive stereocenters consist of two oxindole moieties and a pyrrolidinyl core, including vicinal spiroquaternary stereocenters fused in one ring structure were smoothly obtained in high yields (up to 93% yield) with good diastereoselectivity (up to >20:1). Another valuable application of this method was for the design of new hybrid architectures for biological screening through the adequate fusion of these sub-units of turmerone and 3,3'-pyrrolidinyl-dispirooxindole, generating drug-like molecules.

| S-EPMC6154684 | biostudies-literature

Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharides.

Project description:The use of an N-acyloxazolidinone-protected S-adamantanyl thiosialoside allows the highly stereoselective, one-pot multicomponent synthesis of alpha-sialoside-based oligosaccharides.

| S-EPMC2726932 | biostudies-literature

Synthesis of new functionalized thiazolo pyridine-fused and thiazolo pyridopyrimidine-fused spirooxindoles via one-pot reactions.

Project description:A sequential multi-component reaction of the nitroketene dithioacetals, cysteamine hydrochloride, isatin and different CH-acids is described. This efficient method provides new functionalized thiazolo pyridine-fused spirooxindoles and thiazolo pyridopyrimidine-fused spirooxindoles in good yields. In the case of using isatin derivatives (5-bromoisatin and 5-chloroisatin), the reaction was carried out by using nano-SiO2 (20 mol%) as an effective heterogeneous Lewis acid promoter. This type of reaction provides a range of skeletally different polycyclic spiro thiazole-based heterocyclic structures and represents attractive advantages including straightforward one-pot operation under the catalyst-free condition and simple workup procedures without using tedious purification procedure.

| S-EPMC7114753 | biostudies-literature

One-pot synthesis of 1-alkyl-1H-indazoles from 1,1-dialkylhydrazones via aryne annulation.

Project description:The reaction of readily accessible 1,1-dialkylhydrazones with commercially available o-(trimethylsilyl)aryl triflates provides a direct one-step route to pharmaceutically important 1-alkylindazoles. The products are obtained in high yields by one-pot NCS-chlorination/aryne annulation or Ac(2)O-acylation/deprotection/aromatization protocols.

| S-EPMC3764999 | 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 synthesis of highly substituted N-fused heteroaromatic bicycles from azole aldehydes.

Project description:An efficient route to substituted N-fused aromatic heterocycles, including indolizines, imidazo[1,2-a]pyridines, and imidazo[1,5-a]pyridines from azole aldehydes, is reported. Wittig olefination of the aldehydes with fumaronitrile and triethylphosphine affords predominantly E-alkenes that undergo rapid cyclization upon treatment with a mild base. Substituent control of the 1-, 2-, and 3-positions of the resulting heteroaromatic bicycles is shown. Alternatively, the isolable E-alkene undergoes selective alkylation with electrophiles, followed by in situ annulation to indolizines additionally substituted at the 6-position.

| S-EPMC4500639 | biostudies-literature

Facile One-Pot Synthesis of Functionalized Quinoline-Fused Fluorescent Dihydro/Spiro-quinazolinone Derivatives.

Project description:A facile and efficient method has been developed for the synthesis of quinoline-fused fluorescent dihydro/spiro-quinazolinones. A plausible mechanism involving an acid-mediated enaminone intermediate is provided. The reaction proceeded using p-toluene sulfonic acid as a green promoter. The methodology was successful in synthesizing various quinoline-appended spiro-quinazolinones 4a-o. The synthetic utility of compounds 4a-o was demonstrated by synthesizing compounds 6a-d via Suzuki coupling as a key reaction. Significantly, the π-π* electronic transition of compounds 4c and 4k showed a blue shift. The molar extinction coefficient (ε), Stoke's shift (Δu̅), and quantum yield (Φf)c were calculated for these derivatives (4c and 4k).

| S-EPMC9219092 | 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