Demircan, AydinKandemir, Muhammet K.Colak, MedineKaraarslan, Muhsin2019-08-012019-08-0120160039-78811437-210Xhttps://dx.doi.org/10.1055/s-0035-1562458https://hdl.handle.net/11480/3579A 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.eninfo:eu-repo/semantics/closedAccesscycloadditioncascade reactionsintramolecular Diels-Alder reactionheterocyclesfuranArticle48172873288010.1055/s-0035-15624582-s2.0-84979210513Q1WOS:000384022700019Q2