dc.contributor.author | SCANLAN, EOIN | en |
dc.date.accessioned | 2014-11-24T16:41:43Z | |
dc.date.available | 2014-11-24T16:41:43Z | |
dc.date.issued | 2004 | en |
dc.date.submitted | 2004 | en |
dc.identifier.citation | Scanlan, Eoin M.; Slawin, Alexandra M. Z.; Walton, John C., Preparation of b- and g-lactams from carbamoyl radicals derived from oxime oxalate amides., Organic & Biomolecular Chemistry, 2, 2004, 716, 724 | en |
dc.identifier.other | Y | en |
dc.identifier.uri | http://hdl.handle.net/2262/72177 | |
dc.description | PUBLISHED | en |
dc.description.abstract | A general synthetic route to oxime oxalate amides was developed and applied to the preparation of molecules
incorporating
N
-benzyl-
N
-alkenyl amides linked with acetone oxime or benzaldoxime units. In addition,
2-substituted-thiazolidine-4-carboxylic acid methyl ester amides of oxalyl benzaldoxime were also prepared. It was
shown by EPR spectroscopy that the oxalyl benzaldoxime amides dissociated to produce benziminyl and carbamoyl
(aminoacyl) radicals when photolysed with 4-methoxyacetophenone as a photosensitizer. Carbamoyl radicals derived
from
N
-alk-3-enyl oxime oxalate amides underwent ring closure to a
ff
ord pyrrolidin-2-ones. The analogous
N
-alk-2-
enyl precursors a
ff
orded azetidin-2-ones. Reactions of the cyclohexenyl and cinnamyl oxime oxalate amides a
ff
orded
a bicyclic
β
-lactam and a 3-benzyl-substituted
β
-lactam respectively. Interestingly, both products were isolated as
hydroxylated compounds. A thiazolidine-derived oxime oxalate amide containing an isobutenyl side chain also
dissociated with production of the corresponding thiazolidinyl-carbamoyl radical, as shown by EPR spectroscopy.
GC-MS evidence indicated that this radical cyclised to a
ff
ord some of the corresponding penicillin derivative | en |
dc.format.extent | 716 | en |
dc.format.extent | 724 | en |
dc.language.iso | en | en |
dc.relation.ispartofseries | Organic & Biomolecular Chemistry | en |
dc.relation.ispartofseries | 2 | en |
dc.rights | Y | en |
dc.subject | Chemistry | en |
dc.title | Preparation of b- and g-lactams from carbamoyl radicals derived from oxime oxalate amides. | en |
dc.type | Journal Article | en |
dc.type.supercollection | scholarly_publications | en |
dc.type.supercollection | refereed_publications | en |
dc.identifier.peoplefinderurl | http://people.tcd.ie/scanlae | en |
dc.identifier.rssinternalid | 50439 | en |
dc.rights.ecaccessrights | openAccess | |