One-Pot Cascade Synthesis of Fused Nitrogen-Containing Heterocycles in Aqueous Media - Utility of N-Protective Groups in Intramolecular Diels-Alder Reaction of Furan

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dc.contributor.authorDemircan, Aydin
dc.contributor.authorKandemir, Muhammet K.
dc.contributor.authorColak, Medine
dc.contributor.authorKaraarslan, Muhsin
dc.date.accessioned2019-08-01T13:38:39Z
dc.date.available2019-08-01T13:38:39Z
dc.date.issued2016
dc.departmentNiğde ÖHÜ
dc.description.abstractA metal-free, thermal, intramolecular Diels-Alder (IMDA) reaction of furan in aqueous media without the use of microwave irradiation was investigated. Protection of the amine functionality and the cycloaddition reaction were performed as a one-pot, two-component process. Various nitrogen-protecting groups and their electronic and steric effects on the cycloaddition reaction were studied. The protection-intramolecular Diels-Alder reaction sequence proceeds under environmentally benign aqueous conditions, which are tolerated by substrates with a broad range of nitrogen-protecting groups such as benzyloxycarbonyl (Cbz), trityl, tert-butoxycarbonyl (Boc), trifluoroacetyl, tosyl, mesyl, and p-nosyl [(4-nitrophenyl)sulfonyl]. This study allowed the development of a stereoselective, tandem allylamine isomerization-Diels-Alder cycloaddition sequence leading to the rapid assembly of complex nitrogen-containing heterocycles in a simple one-pot process.
dc.description.sponsorshipScientific and Technological Research Council of Turkey TUBITAK [PN: 107T831]
dc.description.sponsorshipThe authors are grateful to The Scientific and Technological Research Council of Turkey TUBITAK (PN: 107T831) for financial support of this work. We thank Dr. Davit Jishkariani at the University of Pennsylvania, USA, for proofreading.
dc.identifier.doi10.1055/s-0035-1562458
dc.identifier.endpage2880
dc.identifier.issn0039-7881
dc.identifier.issn1437-210X
dc.identifier.issue17
dc.identifier.scopus2-s2.0-84979210513
dc.identifier.scopusqualityQ1
dc.identifier.startpage2873
dc.identifier.urihttps://dx.doi.org/10.1055/s-0035-1562458
dc.identifier.urihttps://hdl.handle.net/11480/3579
dc.identifier.volume48
dc.identifier.wosWOS:000384022700019
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthor[0-Belirlenecek]
dc.language.isoen
dc.publisherGEORG THIEME VERLAG KG
dc.relation.ispartofSYNTHESIS-STUTTGART
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectcycloaddition
dc.subjectcascade reactions
dc.subjectintramolecular Diels-Alder reaction
dc.subjectheterocycles
dc.subjectfuran
dc.titleOne-Pot Cascade Synthesis of Fused Nitrogen-Containing Heterocycles in Aqueous Media - Utility of N-Protective Groups in Intramolecular Diels-Alder Reaction of Furan
dc.typeArticle

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