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Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives
dc.creator | Yucel, Baris | |
dc.creator | Valentić, Nataša | |
dc.creator | Noltemeyer, Mathias | |
dc.creator | de Meijere, Armin | |
dc.date.accessioned | 2021-03-10T10:48:29Z | |
dc.date.available | 2021-03-10T10:48:29Z | |
dc.date.issued | 2007 | |
dc.identifier.issn | 1434-193X | |
dc.identifier.uri | http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1171 | |
dc.description.abstract | A palladium-catalyzed reaction of methylenespiropentane (11) with iodobenzene (12) under typical Heck conditions [Pd(OAC)(2), PPh3, Et3N, DMF] produced a mixture of the unstable [3]dendralene 13 and allylidenecyclopropane 14 in 38 % yield. When an analogous reaction with iodobenzene was carried out in the presence of morpholine (25) and of tris(2-furyl)phosphane (TFP) instead of triphenylphosphane, the dienes 26, 28 and 31 were generated by nucleophilic trapping of pi-allylpalladium intermediates 30 and 32. The cross coupling of methylenespiropentane (11) with the functionalized aryl iodides 33a-g in the presence of a palladium precatalyst [Pd(OAc)2, TFP, Et3N, DMF] at 80 degrees C, 3 h, provided the seven-membered 3,4-dimethylene-substituted heterocycles 34a-g and 35b which, upon addition of dimethyl fumarate (19), underwent Diels-Alder reactions to furnish bicyclic and higher oligocyclic dihydrobenzoxepine and -benzazepine derivatives 36a-g and 37b, yet in rather moderate yields of 18-29 % only. The overall process constitutes a one-pot, two-step, three-component queuing cascade. ( | en |
dc.publisher | Wiley-VCH Verlag Gmbh, Weinheim | |
dc.rights | restrictedAccess | |
dc.source | European Journal of Organic Chemistry | |
dc.subject | pi-allylpalladium species | en |
dc.subject | benzazepine | en |
dc.subject | benzoxepine | en |
dc.subject | bicyclopropylidene | en |
dc.subject | methylenespiropentane | en |
dc.title | Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives | en |
dc.type | article | |
dc.rights.license | ARR | |
dc.citation.epage | 4090 | |
dc.citation.issue | 24 | |
dc.citation.other | 2007(24): 4081-4090 | |
dc.citation.rank | M21 | |
dc.citation.spage | 4081 | |
dc.citation.volume | 2007 | |
dc.identifier.doi | 10.1002/ejoc.200700354 | |
dc.identifier.scopus | 2-s2.0-34548083408 | |
dc.identifier.wos | 000249057500014 | |
dc.type.version | publishedVersion |