Search results for "Bicyclic molecule"

showing 10 items of 254 documents

Reactions of 1-isopropyl-3-methyl- and 2,3-dimethylindoles with triethyl orthoformate: New trisindolylmethanes

1987

Indoles 1 and 2 react with triethyl orthoformate under proton–catalyzed conditions to form trisindolylmethanes. The regioisomer distribution of the products is controlled by steric and electronic factors.

Steric effectschemistry.chemical_compoundchemistryBicyclic moleculeOrganic ChemistryStructural isomerOrganic chemistryOrthoesterNuclear magnetic resonance spectroscopyTriethyl orthoformateIsopropylJournal of Heterocyclic Chemistry
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Triazolopyridines. 14. Substitution reactions of 7-amino[1,2,3]triazolo[1,5-a]pyridines.

1993

Abstract Reaction between 7-aminotriazolopyridines 1 or 2 and sulphuric acid gives hydroxyalkylpyridines 3 and 4 ; bromination gives brominated pyridine 5 or triazolopyridine 6. The anions from amines 1 or 2 are ambident, acylating on N but alkylating on N or on C6; in the latter case triazolylalkenylcyanides 16 – 20 or the 6,6-dialkylated derivative 19 are obtained. An X-ray diffraction study has confirmed structure 19.

Substitution reactionbiologyBicyclic moleculeOrganic ChemistryHalogenationBiochemistryMedicinal chemistrychemistry.chemical_compoundchemistryDrug DiscoveryPyridineX-ray crystallographybiology.proteinTriazolopyridineDerivative (chemistry)Organic anionTetrahedron
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Exploring reactivity of a bis-sulfonium zirconocene-ate dimer: synthesis of various zwitterionic phosphonium anionic zirconocene complexes

2007

Abstract Formal [3+2] cycloaddition reactions between the bis-sulfonium zirconocene-ate dimer 1a and methylpropiolate, benzaldehyde and carbon disulfide afforded stable zwitterionic phosphonium zirconocene-ate complexes 2–4, respectively, with two orthocondensed five-membered heterocycles. X-ray crystal structure of 4 has been determined. Elemental chalcogens (S, Se, Te) gave rise also to a new variety of five-coordinate zirconium(IV) complexes (5–7) by a formal [3+1] cycloaddition reaction. In these bicyclic zirconates, sulfur is included in a five-membered ring while the second chalcogen is in a four-membered one.

SulfoniumDimer010402 general chemistry01 natural sciencesBiochemistryMedicinal chemistryInorganic ChemistryBenzaldehydechemistry.chemical_compoundChalcogenanionic zirconoceneMaterials ChemistryOrganic chemistry[CHIM.COOR]Chemical Sciences/Coordination chemistryReactivity (chemistry)PhosphoniumPhysical and Theoretical ChemistryComputingMilieux_MISCELLANEOUSBicyclic molecule010405 organic chemistrysulfoniumOrganic Chemistry[ CHIM.COOR ] Chemical Sciences/Coordination chemistryzirconocene-atephosphoniumCycloaddition3. Good health0104 chemical scienceschemistrychalcogenszwitterionic complexes
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Synthesis of a new family of bi- and polycyclic compounds via Pd-catalyzed amination of 1,7-di(3-bromobenzyl)cyclen

2008

Abstract New bicyclic cryptand type compounds are synthesized by reacting 1,7-di(3-bromobenzyl)cyclen with 1 equiv of linear polyamines under dilute conditions using Pd-catalyzed amination. Bis(cyclen) and tris(cyclen) compounds containing linear polyamine linkers between benzylated cyclens are obtained by a similar procedure using different reaction conditions. Cyclization of these species via intramolecular catalytic diamination led to tri- and tetracyclic polyaza compounds.

TrisCryptand010402 general chemistry01 natural sciencesBiochemistryMedicinal chemistrycyclenCatalysischemistry.chemical_compoundCyclen[ CHIM.ORGA ] Chemical Sciences/Organic chemistryDrug DiscoveryOrganic chemistryComputingMilieux_MISCELLANEOUSAminationPd-catalyzed aminationBicyclic molecule[CHIM.ORGA]Chemical Sciences/Organic chemistry010405 organic chemistryOrganic Chemistrybicyclic cryptand0104 chemical scienceschemistryIntramolecular forcefunctionalizationPolyamineTetrahedron Letters
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Antimykotische Wirkstoffe, Mitt. Chlor-(1-piperazinyl)-1,3,5-triazine

1988

Aus der Umsetzung von Cyanurchlorid (1) mit den Piperazinderivaten 2a–c bei –20 bis 10° gehen die Dichlor-(1-piperazinyl)-1,3,5-triazine 3a–c hervor. Bei der erhohten Reaktionstemperatur von 40° erfolgt aus 1 und den Piperazinderivaten 4a–b Bildung der 2-Chlor-4,6-bis(piperazinyl)-1,3,5-triazine 5a–b. Zu gemischt substituierten Chlor-1,3,5-triazinen 9 fuhrt die nacheinander erfolgende Umsetzung von 1 mit 2 verschiedenen cyclischen sekundaren Aminen (6 und 8). Die Strukturtypen 3, 5 und 9 zeigen in den 1H-NMR-Spektren zwei fur Piperazinringe charakteristische Signalgruppen im Bereich 2.4–4.0 ppm. Unter den neu entwickelten Verbindungen finden sich Vertreter mit sehr starker antimykotischer W…

biologyBicyclic moleculeStereochemistryCyanuric chloridePharmaceutical ScienceTrichophyton rubrumbiology.organism_classificationPiperazinechemistry.chemical_compoundReaction temperaturechemistryDrug DiscoveryMicrosporum canisMicrosporumArchiv der Pharmazie
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New umbelliferone sesquiterpene ethers from roots ofLigularia persica

1991

An extract of roots of Ligularia persica yielded thirteen umbelliferone sesquiterpene ethers, among them the new ones ligupersin A (11) and ligupersin B (13).

biologyBicyclic moleculeStereochemistryLigulariaOrganic ChemistryEtherNuclear magnetic resonance spectroscopySesquiterpenebiology.organism_classificationUmbelliferoneCoumarinchemistry.chemical_compoundchemistryOrganic chemistryPhysical and Theoretical ChemistryLiebigs Annalen der Chemie
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Synthesis of conformationally restricted 1,2,3-triazole-substituted ethyl β- and γ-aminocyclopentanecarboxylate stereoisomers. Multifunctionalized al…

2010

Abstract Stereoisomers of 1,2,3-triazole-functionalized, conformationally restricted β- or γ-amino esters with a cyclopentane skeleton were efficiently synthetized from the bicyclic β-lactam 6-azabicyclo[3.2.0]hept-3-en-7-one (1) and Vince γ-lactam (15) in five or six steps involving the azide–alkyne 1,3-dipolar cycloaddition of azido-substituted amino ester stereoisomers with nonsymmetric acetylenes. The azide–alkyne click reactions were investigated under thermal and Cu(I)-catalyzed conditions. Surprisingly, the thermally induced cycloaddition furnished the corresponding 1,4-triazoles regioselectively, which also took place selectively in response to Cu(I) catalysis.

chemistry.chemical_classification123-TriazoleAmino estersBicyclic moleculeStereochemistryOrganic ChemistryBiochemistryChemical synthesisCycloadditionchemistry.chemical_compoundAlicyclic compoundchemistryDrug Discovery13-Dipolar cycloadditionClick chemistryTetrahedron
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Stereoselective Conjugate Addition of Mixed Organoaluminum Reagents to ?,?-Unsaturated N-Acyloxazolidinones Derived from Carbohydrates.

2005

The stereoselective synthesis of β-branched carboxylic acid derivatives was accomplished by conjugate addition of mixed organoaluminum reagents to chiral α,β-unsaturated N-acyloxazolidinones. Mixed organoaluminum reagentswere generated in situ by transmetalation of Grignard or organolithium compounds with methylaluminum dichloride. Efficient stereocontrol was achieved using different bicyclic glycosamine-derived oxazolidinones, yielding alternatively (R)- or (S)-configured β-branched carboxylic acid derivatives.

chemistry.chemical_classificationAddition reactionTransmetalationchemistryBicyclic moleculeOrganolithium compoundsReagentCarboxylic acidOrganic chemistryStereoselectivityGeneral MedicineConjugateChemInform
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Stereoselective Synthesis of the Glycosidase Inhibitor Australine through a One-Pot, Double-Cyclization Strategy

2006

[reaction: see text] A stereocontrolled, convergent synthesis of the alkaloid australine, a glycosidase inhibitor of the pyrrolizidine class, is described. The chiral starting materials were ketone 3, derived from L-erythrulose, and alpha-alkoxy aldehyde 4, prepared from L-malic acid. A key step of the synthesis was the highly stereoselective aldol reaction between 4 and a Z boron enolate derived from 3. Another key step was the one-pot construction of the bicyclic pyrrolizidine system by means of a three-step sequence of SN2 displacements induced by benzylamine on a trimesylate precursor.

chemistry.chemical_classificationAldehydesKetoneGlycoside HydrolasesMolecular StructureBicyclic moleculeStereochemistryOrganic ChemistryConvergent synthesisStereoisomerismKetonesBiochemistryAldehydechemistry.chemical_compoundBenzylaminechemistryAldol reactionCyclizationPyrrolizidineSN2 reactionEnzyme InhibitorsPhysical and Theoretical ChemistryPyrrolizidine AlkaloidsOrganic Letters
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ChemInform Abstract: Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Qua…

2010

Cyclization of the chiral imino lactones with allylic or propargylic groups required acidic conditions to afford spirocyclic (II) or (XII).

chemistry.chemical_classificationAllylic rearrangementchemistryBicyclic moleculeIntramolecular forceIminiumGeneral MedicineMedicinal chemistryIonAmino acidChemInform
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