0000000000017528

AUTHOR

Josep Bonjoch

0000-0002-5551-6720

showing 2 related works from this author

Translocation versus cyclisation in radicals derived from N-3-alkenyl trichloroacetamides

2011

Under radical reaction conditions, two different and competitive reaction pathways were observed for N-(alpha-methylbenzyl)trichloroacetamides with a N-3-cyclohexenyl substituent: 1,4-hydrogen translocation and radical addition to a double bond. However, for radicals with an acyclic alkenyl side chain, the direct cyclisation process was exclusively observed. The dichotomy between translocation and direct radical cyclisation in these substrates has been theoretically studied using density functional theory (DFT) methods at the B3LYP/6-31G** computational level.

Models MolecularFree RadicalsDouble bondStereochemistryRadicalSubstituentChromosomal translocationAlkenesBiochemistryPolarizable continuum modelchemistry.chemical_compoundQUIMICA ORGANICAAcetamidesQUIMICA ANALITICASide chainMoleculeTOOLChloroacetatesTrichloroacetic AcidPhysical and Theoretical ChemistryAMIDESchemistry.chemical_classificationMolecular StructureChemistryOrganic ChemistryCOPPER-COMPLEXESCyclizationPOLARIZABLE CONTINUUM MODELDensity functional theory
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Functionalized 2-azabicyclo[3.3.1]nonanes. IV. synthesis of the indolo[3,2-f]morphan system.

1982

Abstract A short route to the 2-azabicyclo[3.3.1]nonan-7-one system is described. Condensation of 4-piperidones with diethyl 2-oxopropylphosphonate, followed by catalytic hydrogenation furnished the corresponding piperidylpropanones 6 which were cyclized with mercuric acetate in acetic acid to the target target bicyclic ketones 1 . The Fischer indole synthesis from 1 a afforded regioselectively the indole [3,2-f]morphan 2 , a new heteromorphan type.

Indole testBicyclic moleculeChemistryOrganic ChemistryCondensationMercuric acetateBiochemistryMorphanAcetic acidchemistry.chemical_compoundFischer indole synthesisDrug DiscoveryOrganic chemistryCatalytic hydrogenationTetrahedron
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