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

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...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 12; pp. 1975 - 1980
Main Authors Loughlin, Wendy A., Henderson, Luke C., Elson, Kathryn E., Murphy, Michelle E.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 14.06.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
cyclizations
amines
oxazoles
pyrroles
parallel synthesis
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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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-942390