Chemicals and DrugsPhenomena and Processes
AziridinesAlkadienesAzirinesVinyl CompoundsMolecular StructureStereoisomerism
Polyfunctional aziridineAsymmetric SynthesisCyclizationEpoxidesDerivativeReactionPreparationAminoYieldsMarketAminesEpoxides and AziridinesSynthesis of AziridinesIsocyanatesTrans-aziridinesReagentAllylic sulfonamidesCrosslinkersCross-linkerAzetidinesCyclicOrganolithiumRearrangementCarbonReactiveAlkylNitrogenPolymerizationChemistryNucleophileComputationalEvaluationMildChlorinating agentsChemicalHighGroupsProductRing-OpeningTypeAlternativeFullShown
Polyfunctional aziridine2
  • PolyAziridine Global pledges to address this by offering not just a complete line of polyfunctional aziridine cross-linkers but also to provide the technical support so important to their successful use. (polyaziridineglobal.com)
  • The request noted concerns about workers' exposure to a new, two-component, water-based polyurethane paint (water-based polyurethane paint with polytetrafluoroethylene and a polyfunctional aziridine cross-linker) that is applied to automotive/truck rubber seals (vehicle sealing) on the dual durometer (DD) extrusion lines. (cdc.gov)
Asymmetric Synthesis1
  • A convenient protocol for the asymmetric synthesis of stereodefined aziridine-2-carboxylic acid derivatives from alpha,beta-unsaturated acryloyl- and crotonoyl camphor sultams is reported. (metu.edu.tr)
Cyclization3
  • Less hindered aziridines can be obtained in high yields by tosylation and in situ cyclization effected by potassium hydroxide in water/dichloromethane. (organic-chemistry.org)
  • Ghorai, Manas K. (2020) Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes The Journal of Organic Chemistry, 85 (2). (ias.ac.in)
  • A mild one-pot stereospecific synthetic route to highly functionalized imidazolidines and oxazolidines via SN2-type ring-opening of the corresponding activated aziridines and epoxides with amines followed by p-toluenesulfonic acid (PTSA)-catalyzed intramolecular cyclization with aldehydes has been developed. (ias.ac.in)
Epoxides1
  • Morandi, B. Atom-economical cobalt-catalysed regioselective coupling of epoxides and aziridines with alkenes. (mpg.de)
Derivative1
  • An example is the development of a unified platform for the enantioselective synthesis of a- and ß-substituted amines and ethers, some of the most ubiquitous scaffolds in medicinal chemistry, via Ni-catalyzed coupling with radicals derived from acetals, aziridines, and iminium ions accessed via condensation of an amine and carbonyl derivative. (hhs.gov)
Reaction4
  • However, there had been no variant of this reaction for nitrogen-containing rings so far, e.g., for the preparation of aziridines, which are three-membered heterocycles with one nitrogen atom. (chemistryviews.org)
  • Using this reaction allowed them to synthesize highly substituted aziridines (general structure pictured above). (chemistryviews.org)
  • The living anionic polymerization of activated aziridines: a systematic study of reaction conditions and kinetics. (mpg.de)
  • It can be manufactured through the ammonolysis of isethionic acid or the reaction of aziridine with sulfurous acid. (lookchem.com)
Preparation1
  • Preparation methods of aziridine-2-carboxylates are discussed. (heterocycles.jp)
Amino2
  • Two alternative and complementary one-pot procedures for the direct transformation of 2-amino alcohols to N -tosyl aziridines are presented. (organic-chemistry.org)
  • The present study reports the crystal structures of two enzyme-inhibitor complexes of DAP epimerase from Arabidopsis thaliana with different isomers of the irreversible inhibitor and substrate mimic, 2-(4-amino-4-carboxybutyl)-aziridine-2-carboxylate, at 1.95 and 2.3 A resolution. (rcsb.org)
Yields1
  • The desired aziridine products were obtained in moderate to good yields in many cases. (chemistryviews.org)
Market1
  • PolyAziridine Global is dedicated to the aziridine crosslinker market and to be the repository of this technology. (polyaziridineglobal.com)
Amines5
  • Ring opening of aziridines with amines takes place readily in the presence of catalytic amount of ytterbium triflate, giving the corresponding 1, 2-diamines in good to high yields. (elsevier.com)
  • Allylic amines from aziridine 17 . (beilstein-journals.org)
  • Recently, we described a Pd(II)-catalyzed process for β-C-H amination on hindered alkyl amines to form aziridines, which proceeded by direct intramolecular C-N reductive elimination from an aminoalkyl Pd(IV) intermediate. (europa.eu)
  • Reaction of vinyl triflates of α-keto esters with primary amines: efficient synthesis of aziridine carboxylates. (hapinutrition.co.uk)
  • My long-standing claim has been that nature does not know how to make C-N bonds by oxidation, which culminates in the inability of biosynthesis to produce aziridines (and other amines) by oxidative C-N bond formation. (amphoteros.com)
Epoxides and Aziridines3
  • de los Santos JM , Ochoa de retana AM, Martínez de marigorta E, Vicario J, Palacios F. Catalytic Asymmetric Darzens and Aza‐Darzens Reactions for the Synthesis of Chiral Epoxides and Aziridines. (wjgnet.com)
  • Deprotonation of terminal epoxides and aziridines with organolithium/diamine combinations or lithium amides allows the regio- and stereoselective formation of α-lithiated species. (iupac.org)
  • The intermediate 2a,3a- and 2ß,3ß-epoxides and aziridines were cleaved to vicinal trans-diaxial amino- and azido-alcohols, which in turn yielded the isomers by a series of functional group inversions and transformations. (hw.ac.uk)
Synthesis of Aziridines1
Isocyanates2
  • There are two common crosslinking agents used in waterbornes: aziridines and isocyanates. (woodweb.com)
  • In general, these systems are not toxic and dangerous, as are aziridines and isocyanates. (woodweb.com)
Trans-aziridines4
  • Chapter 1 and 2 detailed the use of organocatalysts sulfenate anion (RSO-) and selenenate anion (RSeO-) to catalyze the synthesis of trans-aziridines, trans-stilbenes, and ppv (poly(p-phenylene vinylene))-type polymers with good to excellent yields. (upenn.edu)
  • In Chapter 1, a broadly applicable and diastereoselective synthetic method is reported for the synthesis of trans-aziridines from imines and benzylic or alkyl halides utilizing sulfenate anions (PhSO-) as the catalyst. (upenn.edu)
  • Zheng, Zhipeng, "Catalytic Synthesis Of Trans-Aziridines, Trans-Stilbenes And Bulky Pyridine-Based Ligands" (2020). (upenn.edu)
  • The catalytic reaction produces both cis and trans-aziridines. (ttu.edu)
Reagent4
  • The product distributions are highly dependent on the organolithium reagent employed and the structure of the methoxy aziridine Thus, together with our previous reports, the full scope and limitations of this approach to allylic sulfonamides are established. (lancs.ac.uk)
  • Magnesium metal in methanol was used as a simple electron transfer induced ring-opening reagent of 2-(bromomethyl)aziridines to afford allylamines derivatives in 70-90% yield. (uantwerpen.be)
  • This involved the reduction of a 1,2-azido alcohol, using a solid-supported triphenylphosphine reagent, to an aziridine that undergoes conjugate addition onto a tethered dehydroamino acid in situ. (bl.uk)
  • A Highly Potent Reagent for Regioselective and Stereospecific Synthesis of Polyenes Bearing Terminal Aziridine Groups. (unamur.be)
Allylic sulfonamides1
  • The organolithium-mediated conversion of cyclic trans-p-methoxy aziridines and cis-beta-methoxy aziridines with a tertiary alkoxy group adjacent to the aziridine into the corresponding substituted allylic sulfonamides is reported. (lancs.ac.uk)
Crosslinkers1
  • They are an excellent alternative for more hazardous isocyanate and aziridine crosslinkers. (com.vn)
Cross-linker1
  • Occupational asthma and contact dermatitis in a spray painter after introduction of an aziridine cross-linker. (nih.gov)
Azetidines1
  • This research involves the study of regio- and stereoselective ring transformations of constrained (phosphonylated) azaheterocycles such as aziridines, azetidines and beta-lactams. (ugent.be)
Cyclic1
  • Here, we demonstrate a conjugation strategy whereby cyclic RGD-containing macrocycles are prepared using aziridine aldehydes, isocyanides, and linear peptides, followed by conjugation to a cysteamine linker. (utoronto.ca)
Organolithium1
  • Organolithium-induced alkylative ring opening of aziridines: synthesis of unsaturated amino alcohols and ethers. (ox.ac.uk)
Rearrangement2
  • Synthesis and rearrangement of aziridine 1a . (beilstein-journals.org)
  • A variety of N-butenyl substituted pyrroles have been found to undergo an extraordinary photocycloaddition/rearrangement sequence to give tricyclic fused aziridines of high molecular complexity. (ukri.org)
Carbon1
  • The presented work concerning the reactivity of 2-bromomethyl-1-tosylaziridine stands in contrast to the behaviour of the corresponding 1-tosyl-2-(tosyloxymethyl)aziridine with respect to nucleophiles, which undergoes a clean ring-opening/ring-closure process with inversion of configuration at the asymmetric aziridine carbon atom. (ugent.be)
Reactive1
  • The resulting aziridines will themselves be reactive species and should undergo a number of useful bond forming ring opening reactions. (ukri.org)
Alkyl1
  • The niobium complex NbCl, in combination with NBu4I, emerged as the best catalyst of the overall series to convert aziridines with small N-alkyl substituents into the corresponding 5-aryl-oxazolidin-2-ones. (pubfacts.com)
Nitrogen1
  • Over the past few years, we have studied molecular motion in the form of nitrogen inversion in aziridines. (bham.ac.uk)
Polymerization3
  • Living Anionic Polymerization of Functional Aziridines. (mpg.de)
  • Aziridine Termination of Living Anionic Polymerization. (mpg.de)
  • and the branched form, produced by cationic polymerization of aziridine monomers. (medscape.com)
Chemistry1
  • Modeling studies showed that aziridine aldehyde cyclization chemistry stabilized the RGD motif into the required bioactive conformation and that this cyclization chemistry modulated the geometry of macrocycles of different residue lengths. (utoronto.ca)
Nucleophile1
  • According to these computational analyses, the synthesis of chiral 2-substituted 1-tosylaziridines can take place with inversion (through ring opening/ring closure) or retention (through direct bromide displacement) of configuration upon treatment of the corresponding 2-(bromomethyl)aziridines with one equivalent of a nucleophile, whereas chiral 2-substituted 1-benzylaziridines are selectively obtained with retention of configuration (via direct bromide displacement). (ugent.be)
Computational1
  • To verify the computational findings experimentally, chiral 1-benzyl-2-(bromomethyl)aziridines and 2-bromomethyl-1-tosylaziridines were treated with sodium methoxide in methanol. (ugent.be)
Evaluation3
  • Genetic Toxicity Evaluation of Aziridine in Salmonella/E.coli Mutagenicity Test or Ames Test. (nih.gov)
  • Some aziridines, N-, S- & O-mustards and selenium / this publication represents the views of an IARC Working Group on the Evaluation of the Carcinogenic Risk of Chemicals to Man, which met in Lyon, 8-14 April 1975. (who.int)
  • 6. Novel Class of Proteasome Inhibitors: In Silico and In Vitro Evaluation of Diverse Chloro(trifluoromethyl)aziridines. (nih.gov)
Mild1
  • A mild, selective, palladium-catalyzed boronation of vinyl cyclopropane, vinyl aziridine, and allyl acetate substrates could be accomplished using tetrahydroxydiboron in the presence of a palladium pincer complex catalyst to give synthetically useful linear trifluoro(allyl)borates or allyl boronates incorporating a trans double bond. (organic-chemistry.org)
Chlorinating agents1
  • Aziridine/ gives the explosive 1-chloroazidine on treatment with /chlorinating agents/ eg sodium hypochlorite solution. (nih.gov)
Chemical1
  • The chemical name for thiotepa is Aziridine, 1,1'1"-phosphinothioylidynetris-, or Tris (1-aziridinyl) phosphine sulfide. (nih.gov)
High1
Groups1
  • Further functionalization of aziridines containing cyclopropyl or cyclobutyl groups was achieved through ring-opening reactions, with a cyclobutyl-substituted norephedrine derivative obtained through a four-step synthesis. (upenn.edu)
Product1
  • Vous pouvez soutenir notre travail en donnant à Open Product Facts et aussi en utilisant le moteur de recherche Lilo . (openproductsfacts.org)
Ring-Opening5
  • However, ring opening was found to be only feasible for the epoxide and the activated aziridine, and not for the non-activated aziridine. (ugent.be)
  • Our method involves site-selective aziridine ring-opening with the nucleophilic sulfhydryl group of cysteamine. (utoronto.ca)
  • Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or b-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N -protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs). (tudublin.ie)
  • The required DAPs were also synthesised by ring-opening of N -protected aziridine 2-carboxylates with para -methoxybenzylamine. (tudublin.ie)
  • O'Brien, K., O Proinsias, K., Kelleher, F.: Synthesis of Orthogonally Protected Azalanthionines (Lanazanines) by Sequential Ring-Opening of N-Substituted Aziridine 2-Carboxylates. (tudublin.ie)
Type1
  • Part A 61 , 1505-1517 ( 2005 ) Development and Validation of a Separation Method for the Diastereomers and Enantiomers of Aziridine-type Protease Inhibitors. (yairtal.com)
Alternative1
Full1
  • Aziridines, in particular, are extremely dangerous, and are generally applied wearing a full body suit with a supplied air respirator. (woodweb.com)
Shown1
  • Once the imine has been consumed, the trans-isomer is shown to undergo a catalytic decomposition, leaving cis-aziridine and by-products. (ttu.edu)