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Investigations into the parallel synthesis of novel pyrrole-oxazole analogues of the insecticide pirate

Loughlin, Wendy A., Henderson, Luke C., Elson, Kathryn E. and Murphy, Michelle E. 2006, Investigations into the parallel synthesis of novel pyrrole-oxazole analogues of the insecticide pirate, Synthesis: journal of synthetic organic chemistry, vol. 12, pp. 1975-1980, doi: 10.1055/s-2006-942390.

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Title Investigations into the parallel synthesis of novel pyrrole-oxazole analogues of the insecticide pirate
Author(s) Loughlin, Wendy A.
Henderson, Luke C.ORCID iD for Henderson, Luke C. orcid.org/0000-0002-4244-2056
Elson, Kathryn E.
Murphy, Michelle E.
Journal name Synthesis: journal of synthetic organic chemistry
Volume number 12
Start page 1975
End page 1980
Publisher Stuttgart, Germany
Place of publication Thieme
Publication date 2006
ISSN 0039-7881
1437-210X
Summary Investigations into the parallel synthesis of selected analogues of a structurally unique pyrrole-oxazole analogue of the pyrrole insecticide pirate, are reported. Acylaminoketone salts were obtained from ketobromides in moderate to high yields and excellent purity. A number of N-tosyl pyrroles were obtained; however, formation of the target acyl tosyl pyrroles was thwarted by the stereoelectronic effects of the pyrrole substituents. During the pyrrole subunit chemistry, an interesting pyrrole derivative, vinyl pyrrole, was isolated. By restricting diversity to the aryl subunit, the parallel synthesis of selected pyrrole-oxazoles in moderate purity, was achieved when electron-donating or no groups were present on the aryl ring.
Language eng
DOI 10.1055/s-2006-942390
Field of Research 030503 Organic Chemical Synthesis
HERDC Research category C1.1 Refereed article in a scholarly journal
Copyright notice ©2006, Georg Thieme Verlag Stuttgart
Persistent URL http://hdl.handle.net/10536/DRO/DU:30028583

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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