Thermal intramolecular Diels-Alder reaction of furan; synthesis of nitrogen tetracycles, isobenzofuran and isobenzothiophene

dc.contributor.authorKaraarslan M.
dc.contributor.authorGokturk E.
dc.contributor.authorDemircan A.
dc.date.accessioned2019-08-01T13:38:39Z
dc.date.available2019-08-01T13:38:39Z
dc.date.issued2007
dc.departmentNiğde ÖHÜ
dc.description.abstractThermal intramolecular Diels-Alder (IMDA) reaction of furan cored compounds has been further investigated; a series of key precursors to the IMDA reaction of furan diene (9a-c) have been prepared via facile alkylation and protection. While the cycloaddition process for (10a-c) was afforded in hot toluene, a commercial microwave (2450 MHz) was used for the synthesis of (12a-b). Treatment of fused oxy- and thio-heterotricycles (12a-b) with borontrifluoride-etherate in dichloromethane at -78°C cleaved epoxy bridge and concomitant aromatisation gave the isobenzo-furan and thiophene (13a-b) in 72-76% yields respectively.
dc.identifier.doi10.3184/030823407X191967
dc.identifier.endpage120
dc.identifier.issn0308-2342
dc.identifier.issue2
dc.identifier.scopus2-s2.0-34248218738
dc.identifier.scopusqualityN/A
dc.identifier.startpage117
dc.identifier.urihttps://dx.doi.org/10.3184/030823407X191967
dc.identifier.urihttps://hdl.handle.net/11480/1229
dc.identifier.wosWOS:000250766800019
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthor[0-Belirlenecek]
dc.language.isoen
dc.relation.ispartofJournal of Chemical Research
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectAromatisation
dc.subjectCycloaddition
dc.subjectIntramolecular Diels-Alder
dc.titleThermal intramolecular Diels-Alder reaction of furan; synthesis of nitrogen tetracycles, isobenzofuran and isobenzothiophene
dc.typeArticle

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