Back to Search
Start Over
A study of three reactions leading to isomeric 2-(N,N-disubstituted amino)thiazol-5-yl ketones
- Source :
- Journal of the Chemical Society, Perkin Transactions 1. :2311
- Publication Year :
- 1987
- Publisher :
- Royal Society of Chemistry (RSC), 1987.
-
Abstract
- N-Imidoyl-N,N-disubstituted thioureas react with α-halogeno ketones in the presence of triethylamine to give the expected 2-(N,N-disubstituted amino) thiazol-5-yl ketones in high yield. The corresponding reactions of N-acyl-N,N-disubstituted thioureas lead to mixtures of these products and isomers which arise from rearrangement between cyclic intermediates. Mixtures of the isomeric thiazolyl ketones are also formed by treating N,N-disubstituted thioureas with 2-bromo 1,3-diketones. The mixtures from the second and third routes contain the same products but in significantly different proportions. A mechanistic scheme which accounts for the main findings was developed.During the work 40 new 2-(N,N-disubstituted amino)thiazol-5-yl ketones were prepared and their structures rigorously established; characteristic mass spectral fragmentation patterns were particularly useful in identifying the substituents at positions 4 and 5 of the thiazole ring.
Details
- ISSN :
- 13645463 and 0300922X
- Database :
- OpenAIRE
- Journal :
- Journal of the Chemical Society, Perkin Transactions 1
- Accession number :
- edsair.doi...........34fb2c2665fa9cc439b06f087c5d100d
- Full Text :
- https://doi.org/10.1039/p19870002311