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dc.creatorJevtić, Ivana I.
dc.creatorDošen-Mićović, Ljiljana
dc.creatorIvanović, Evica R.
dc.creatorTodorović, Nina
dc.creatorIvanović, Milovan
dc.date.accessioned2018-11-22T00:40:40Z
dc.date.available2018-11-22T00:40:40Z
dc.date.issued2017
dc.identifier.issn0039-7881
dc.identifier.urihttps://cherry.chem.bg.ac.rs/handle/123456789/2492
dc.description.abstractThe synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.en
dc.publisherGeorg Thieme Verlag Kg, Stuttgart
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172032/RS//
dc.rightsrestrictedAccess
dc.sourceSynthesis, Stuttgart
dc.subjectheterocyclesen
dc.subjectrearrangementen
dc.subjectacylationen
dc.subjectprotecting groupsen
dc.subjectdiastereoselectivityen
dc.titleSynthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanylen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractИвановић, Милован; Досен-Мицовиц, Љиљана И.; Тодоровиц, Нина М.; Ивановиц, Евица Р.; Јевтиц, Ивана И.;
dc.citation.volume49
dc.citation.issue14
dc.citation.spage3126
dc.citation.epage3136
dc.identifier.wos000406066800009
dc.identifier.doi10.1055/s-0036-1588985
dc.citation.other49(14): 3126-3136
dc.citation.rankM22
dc.description.otherSupplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3249]
dc.type.versionpublishedVersion
dc.identifier.scopus2-s2.0-85017147328
dc.identifier.rcubKon_3308


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