Journal
RSC ADVANCES
Volume 4, Issue 24, Pages 12252-12256Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ra47603k
Keywords
-
Categories
Funding
- CSIR [OLP-0069]
- CSIR
Ask authors/readers for more resources
Solar photo-thermochemical C(sp(3))-H bromination, conducted efficiently in a specially designed reactor, was reported recently. In the present study, the more complex formation of 4-bromo-2,5-substituted oxazoles from N-arylethylamides using this approach was achieved. The one-pot syntheses were carried out with N-bromosuccinimide-dichloroethane over 6 h (10.00 am to 4.00 pm) on sunny days. The isolated yields were in the range 42-82%. Benzylic bromination, followed by O-C bond formation through intramolecular nucleophilic substitution, and a second benzylic bromination followed by HBr elimination, gave the oxazole ring. A third bromination of the ring yielded the final product. The feasibility of synthesizing thiazole derivatives using a similar approach was also demonstrated. During the course of the reactions, succinimide and HBr were co-generated in the aqueous phase. Treatment with NaBrO3 and additional acid returned the reagent in 57% isolated yield upon chilling. The overall methodology was greener as a result.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available