Browse
Submit Data
Databases
API
Help

Dataset Information

16 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines: application in the construction of the communesin ring system.

ABSTRACT: A new protocol for generating aza-ortho-xylylenes via acid-catalyzed or fluoride-promoted ring opening of 2-(2-acylaminophenyl)aziridines is described. This methodology has been exploited in the rapid construction of a hexacyclic substructure of communesin B.

SUBMITTER: Crawley SL

PROVIDER: S-EPMC2547339 | biostudies-literature | 2006 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Generation of aza-ortho-xylylenes via ring opening of 2-(2-acylaminophenyl)aziridines: application in the construction of the communesin ring system.

Crawley Seth L SL Funk Raymond L RL

Organic letters 20060801 18

A new protocol for generating aza-ortho-xylylenes via acid-catalyzed or fluoride-promoted ring opening of 2-(2-acylaminophenyl)aziridines is described. This methodology has been exploited in the rapid construction of a hexacyclic substructure of communesin B. ...[more]

PMID: 16928057

Similar Datasets

Synthesis of ?-substituted tryptamines by regioselective ring opening of aziridines.

Project description:Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis if site selectivity can be controlled. 4-Nitrobenzyl carbamate (PNZ)-protected aziridines undergo regioselective ring opening to produce ?-substituted tryptamines for a series of indoles. The PNZ-protected tryptamines can be further manipulated by PNZ removal under mild conditions.

| S-EPMC4930112 | biostudies-literature

Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines.

Project description:Predominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with ?-bromoallyllithium in the presence of freshly fused ZnCl2. These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally with good regioselectivity.

| S-EPMC3678660 | biostudies-literature

A specific nucleophilic ring-opening reaction of aziridines as a unique platform for the construction of hydrogen polysulfides sensors.

Project description:A hydrogen polysulfide mediated aziridine ring-opening reaction was discovered. Based on this reaction, a novel H2S(n)-specific chemosensor (AP) was developed. AP showed high sensitivity and selectivity for H2S(n). Notably, the fluorescent turn-on product (1) exhibited excellent two-photon photophysical properties, a large Stokes shift, and high solid state luminescent efficiency.

| S-EPMC4460920 | biostudies-literature

Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with ?-Keto Esters

Project description:We herein report an ammonium salt-catalyzed protocol for the regioselective ring opening of aryl-aziridines with ?-keto esters. The reaction gives access to a variety of highly functionalized target molecules with two consecutive stereo-genic centers and can be rendered enantioselective (up to e.r. = 91:9) by using bifunctional chiral ammonium salt catalysts.

| S-EPMC7116117 | biostudies-literature

Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with β-Keto Esters.

Project description:We herein report an ammonium salt-catalyzed protocol for the regioselective ring opening of aryl-aziridines with β-keto esters. The reaction gives access to a variety of highly functionalized target molecules with two consecutive stereo-genic centers and can be rendered enantioselective (up to e.r. = 91:9) by using bifunctional chiral ammonium salt catalysts.

| S-EPMC7508174 | biostudies-literature

Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B2pin2: Experimental and Computational Studies.

Project description:The possibility to form new C-B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individuation of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2pin2) in a regioselective nucleophilic addition reaction under copper catalysis.

| S-EPMC8659106 | biostudies-literature

Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines.

Project description:Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of β-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to β-methyllanthionines and allows production of over 30 g of β-methyllanthionine in a single batch.

| S-EPMC6542561 | biostudies-literature

Ring closing and opening reactions leading to aza-polycyclic aromatic compounds.

Project description:A series of functionalized aza-polycyclic aromatic compounds were prepared by a superacid-promoted ring closing and opening reaction cascade. A reaction mechanism is proposed, which involves reactive dicationic intermediates. A key step in the conversions involves ipso protonation of an aryl group and elimination of an alkyl phenyl group.

| S-EPMC3797622 | biostudies-literature

A Mild and Regioselective Ring-Opening of Aziridines with Acid Anhydride Using TBD or PS-TBD as a Catalyst.

Project description:The ring-opening of N-tosylaziridines with various acid anhydrides catalyzed by 5 mol % of 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) afforded the corresponding ?-amino esters in excellent yields under mild reaction conditions. Polymer-supported catalyst, PS-TBD also acts as a good catalyst for this reaction. PS-TBD was easily recovered and reused with minimal loss of activity.

| S-EPMC6332191 | biostudies-literature

Stereospecific ring expansion of chiral vinyl aziridines.

Project description:In this report, it is demonstrated that chiral vinyl aziridines can be stereospecifically ring expanded. This synthetic approach allows controlled access to chiral 2,5-cis- or 2,5-trans-3-pyrroline products from starting materials with the appropriate aziridine geometry. Twenty three ring expansion examples, most of which feature a stereospecific cyclization, are presented.

| S-EPMC3072884 | 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