{"?xml":{"@version":"1.0"},"edm:RDF":{"@xmlns:dc":"http://purl.org/dc/elements/1.1/","@xmlns:edm":"http://www.europeana.eu/schemas/edm/","@xmlns:wgs84_pos":"http://www.w3.org/2003/01/geo/wgs84_pos","@xmlns:foaf":"http://xmlns.com/foaf/0.1/","@xmlns:rdaGr2":"http://rdvocab.info/ElementsGr2","@xmlns:oai":"http://www.openarchives.org/OAI/2.0/","@xmlns:owl":"http://www.w3.org/2002/07/owl#","@xmlns:rdf":"http://www.w3.org/1999/02/22-rdf-syntax-ns#","@xmlns:ore":"http://www.openarchives.org/ore/terms/","@xmlns:skos":"http://www.w3.org/2004/02/skos/core#","@xmlns:dcterms":"http://purl.org/dc/terms/","edm:WebResource":[{"@rdf:about":"http://www.dlib.si/stream/URN:NBN:SI:doc-LZCZCGGQ/3067952f-b5b2-4198-9393-83e58adc8f30/HTML","dcterms:extent":"60 KB"},{"@rdf:about":"http://www.dlib.si/stream/URN:NBN:SI:doc-LZCZCGGQ/aad81817-2dc8-4709-9b50-71a43f25d28e/PDF","dcterms:extent":"223 KB"},{"@rdf:about":"http://www.dlib.si/stream/URN:NBN:SI:doc-LZCZCGGQ/49fb2754-a185-48c1-ac02-2927a0ddefd5/TEXT","dcterms:extent":"50 KB"}],"edm:TimeSpan":{"@rdf:about":"1998-2025","edm:begin":{"@xml:lang":"en","#text":"1998"},"edm:end":{"@xml:lang":"en","#text":"2025"}},"edm:ProvidedCHO":{"@rdf:about":"URN:NBN:SI:doc-LZCZCGGQ","dcterms:isPartOf":[{"@rdf:resource":"https://www.dlib.si/details/URN:NBN:SI:spr-KC6O72BG"},{"@xml:lang":"sl","#text":"Acta chimica slovenica"}],"dcterms:issued":"2006","dc:creator":["Grošelj, Uroš","Meden, Anton","Rečnik, Simon","Stanovnik, Branko","Svete, Jurij"],"dc:format":[{"@xml:lang":"sl","#text":"12 strani"},{"@xml:lang":"sl","#text":"številka:3"},{"@xml:lang":"sl","#text":"letnik:53"},{"@xml:lang":"sl","#text":"str. 245-256"}],"dc:identifier":["ISSN:1318-0207","COBISSID:27954437","URN:URN:NBN:SI:doc-LZCZCGGQ"],"dc:language":"en","dc:publisher":{"@xml:lang":"sl","#text":"Slovensko kemijsko društvo"},"dc:subject":[{"@xml:lang":"sl","#text":"derivati pirazola"},{"@xml:lang":"sl","#text":"enaminoni"},{"@xml:lang":"sl","#text":"heterociklične spojine"},{"@xml:lang":"sl","#text":"kafra"},{"@xml:lang":"sl","#text":"kondenzacija"},{"@xml:lang":"sl","#text":"NMR spektroskopija"},{"@xml:lang":"sl","#text":"organska kemija"},{"@xml:lang":"sl","#text":"rentgenska strukturna analiza"},{"@xml:lang":"sl","#text":"sinteza"},{"@xml:lang":"sl","#text":"stereoselektivne sinteze"}],"dcterms:temporal":{"@rdf:resource":"1998-2025"},"dc:title":{"@xml:lang":"sl","#text":"Synthesis and transformations of some N-substituted (1R,4S)-3-aminomethylidene-1,7,7-trimethylbicyclo2.2.1-heptan-2-ones|"},"dc:description":[{"@xml:lang":"sl","#text":"Acid-catalysed reactions of (1R,3E,4S)-3-(dimethylamino)methylidene-1,7,7-trimethylbicyclo2.2.1hept an-2 -one (2) with amino acid derivatives 3a-d and pyrazolidin-3-ones 5a-e gave the substitution products 4/4a-d and 6a-e, respectively, in 40-83% yields. Compound 4a was transformed with Bredereckćs reagent into the 3-(dimethylamino)propenoate 7/7. Treatment of 1-{(1R,3Z,4S)-1,7,7-trimethyl-2-oxobicyclo-2.2.1hept-3-ylide-nemethyl}p yrazolidin-3-ones 6a and 6b with dimethyl acetylenedicarboxylate in refluxing anisole furnished the corresponding cycloadducts as mixtures of four diastereomers, the major endo-isomers 10/11a,b and the minor exo-isomers 12/13a,b with moderate endo-selectivity. Chromatographic separation of 10/11/12/13a,b afforded the endo/exo-pairs of diastereomers, 10/13a,b and 11/12a,b. The structures of compounds 4/4, 6, 7/7, and 10/11/12/13were determined by NMR and by X-ray diffraction"},{"@xml:lang":"sl","#text":"Pri kislinsko kataliziranih reakcijah (1R,3E,4S)-3-(dimetilamino)metiliden-1,7,7-trimetilbiciklo-2.2.1heptan- 2-on a (2) z .-aminokislinskimi derivati 3a-d in pirazolidin-3-oni 5a-e poteče izmenjava dimetilaminske skupine, ki vodi do nastanka ustreznih N-substituiranih (1R,4S)-3-aminometiliden-1,7,7-trimetilbiciklo2.2.1heptan-2-onov4/4a-d in 6a-e. Izmenjave dimetilaminske skupine z .-aminokislinskimi derivati 3a-d so vodile do zmesi večinskih (3E)-izomerov 4a-d in manjšinskih (3Z)-izomerov 4a-d, medtem ko so bile pretvorbe enaminona 2 s pirazolidinoni 5a-e stereoselektivne saj so nastali izključno ustrezni (3Z)-izomeri 6a-e. Pretvorba spojine 4a z bis(dimetilamino)-terc-butoksimetanom (Bredereckovim reagentom) je vodila do 3-(dimetilamino)propenoata 7/7. Izvedli smo tudi pretvorbi 1-{(1R,3Z,4S)-1,7,7-trimetil-2-oksobiciklo2.2.1hept-3-ilidenmetil}piraz olid in-3-onov 6a and 6b z dimetil acetilendikarboksilatom (DMAD). V obeh primerih sta nastali ustrezni zmesi štirih diastereomernih spojin, 10/11/12/13a in 10/11/12/13b, z večinskima endo-izomeroma 10 in 11 ter manjšinskima ekso-izomeroma 12 in 13. S preparativno tekočinsko kromatografijo (MPLC) smo zmesi štirih izomerov 10/11, 12/13 uspeli ločiti na dva endo/ekso-para izomerov, 10/13 in 11/12. Strukture produktov so bile potrjene z NMR spektroskopijo in z rentgensko strukturno analizo"}],"edm:type":"TEXT","dc:type":[{"@xml:lang":"sl","#text":"znanstveno časopisje"},{"@xml:lang":"en","#text":"journals"},{"@rdf:resource":"http://www.wikidata.org/entity/Q361785"}]},"ore:Aggregation":{"@rdf:about":"http://www.dlib.si/?URN=URN:NBN:SI:doc-LZCZCGGQ","edm:aggregatedCHO":{"@rdf:resource":"URN:NBN:SI:doc-LZCZCGGQ"},"edm:isShownBy":{"@rdf:resource":"http://www.dlib.si/stream/URN:NBN:SI:doc-LZCZCGGQ/aad81817-2dc8-4709-9b50-71a43f25d28e/PDF"},"edm:rights":{"@rdf:resource":"http://creativecommons.org/licenses/by/4.0/"},"edm:provider":"Slovenian National E-content Aggregator","edm:intermediateProvider":{"@xml:lang":"en","#text":"National and University Library of Slovenia"},"edm:dataProvider":{"@xml:lang":"sl","#text":"Slovensko kemijsko društvo"},"edm:object":{"@rdf:resource":"http://www.dlib.si/streamdb/URN:NBN:SI:doc-LZCZCGGQ/maxi/edm"},"edm:isShownAt":{"@rdf:resource":"http://www.dlib.si/details/URN:NBN:SI:doc-LZCZCGGQ"}}}}