Synthesis of 2-(aminomethyl)aziridines and their microwave-assisted ring opening to 1,2,3-triaminopropanes as novel antimalarial pharmacophores.
@article{Dhooghe2011SynthesisO2, title={Synthesis of 2-(aminomethyl)aziridines and their microwave-assisted ring opening to 1,2,3-triaminopropanes as novel antimalarial pharmacophores.}, author={Matthias D’hooghe and Sara Kenis and Karel Vervisch and Carmen A Lategan and Peter J. Smith and Kelly Chibale and Norbert de Kimpe}, journal={European journal of medicinal chemistry}, year={2011}, volume={46 2}, pages={ 579-87 } }
33 Citations
A new synthesis of 1,3-difunctionalized 2-sulfonamidopropane derivatives via regioselective ring opening reactions of 2-(bromomethyl)-1-sulfonylaziridines by substituted arylsulfonamides
- ChemistryMonatshefte für Chemie - Chemical Monthly
- 2020
Abstract The novel functionalized N , N′ -[2-(arylsulfonamido)propane-1,3-diyl]bis( N -allylarylsulfonamide) and N , N′ -[2-(methylsulfonamido)propane-1,3-diyl]bis( N -benzylarylsulfonamide)…
Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone.
- ChemistryOrganic & biomolecular chemistry
- 2011
Novel primary β-iodo amines were obtained by regioselective ring opening of these 2-(trifluoromethyl)aziridines using alkyl iodides, and their synthetic potential was demonstrated by converting them into novel α-CF(3)-β-phenylethylamines upon treatment with lithium diphenylcuprate.
Chemical and enzymatic synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and their conversion into δ-lactams and γ-lactones.
- ChemistryOrganic letters
- 2012
Chemical hydrolysis of 2-(2-cyanoethyl)aziridines using KOH in EtOH/H(2)O furnished the corresponding potassium 3-(azIRidin-2-yl)propanoates, which, upon acidification with acetic acid, smoothly rearranged into 4-(aminomethyl)butyrolactones.
Syntheses of imidazo-, oxa-, and thiazepine ring systems via ring-opening of aziridines/Cu-catalyzed C-N/C-C bond formation.
- ChemistryThe Journal of organic chemistry
- 2014
A simple and unpredicted synthetic pathway toward racemic and scalemic tetrahydrodibenzoimidazoazepines has been invented serendipitously proceeding through an S(N)2-type ring-opening of N-activated…
Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity
- Chemistry, BiologyBeilstein journal of organic chemistry
- 2011
A variety of 2-amino-3-arylpropan-1-ols, anti-1,2,3-triazol-1 -yl)methyl]aziridines were prepared selectively through elaboration of trans-4-aryl- 3-chloro-β-lactams and showed moderate antiplasmodial activity against both a chloroquine-sensitive and a chlorquine-resistant strain of Plasmodium falciparum.
SYNTHESIS OF ALKYL 3-CHLOROAZETIDINE-3-CARBOXYLATES VIA REGIOSELECTIVE RING TRANSFORMATION OF ALKYL 2-(BROMOMETHYL)AZIRIDINE-2-CARBOXYLATES (Dedicated to Professor Victor Snieckus on the occasion of his 77th birthday)
- Chemistry
- 2014
The synthesis of alkyl 3-chloroazetidine-3-carboxylates was developed by ring transformation of alkyl 2-(bromomethyl)aziridine-2-carboxylates utilizing ring opening with hydrochloric acid at the more…
Syntheses of Tetrahydrobenzodiazepines via SN2-Type Ring-Opening of Activated Aziridines with 2-Bromobenzylamine Followed by Copper-Powder-Mediated C−N Bond Formation
- Chemistry
- 2015
A synthetic route to 2,3,4,5-tetrahydrobenzodiazepines has been devised through an SN2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by an intramolecular cyclization…
Solvent-controlled selective transformation of 2-bromomethyl-2-methylaziridines to functionalized aziridines and azetidines.
- ChemistryThe Journal of organic chemistry
- 2012
The experimentally observed solvent-dependent behavior of 2-bromomethyl-2-methylaziridines was further supported by means of DFT calculations and the choice of the solvent has a profound influence on the reaction outcome.
Enantioselective synthesis of 4,5-dihydropyrroles via domino ring-opening cyclization (DROC) of N-activated aziridines with malononitrile.
- Chemistry, BiologyThe Journal of organic chemistry
- 2013
The DROC reaction serves as a tool for the synthesis of a large variety of substituted 4,5-dihydropyrroles in enantiomerically pure forms.
Chemistry of phosphorus ylides 31: Reaction of azidocoumarin with active phosphonium ylides, synthesis and antitumour activities of chromenones
- ChemistryJournal of Chemical Sciences
- 2013
AbstractThe reaction of 4- azidochromen-2-one (1) with the nucleophilic phosphacumulene ylides 2, 8, and 12 afforded the new heterocyclic triazoles, triazepines, aziridine, pyrrolone containing a…
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