7007-07-0Relevant articles and documents
Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors
Ahn, Gwang-Noh,Kim, Dong-Pyo,Lahore, Santosh,Nikam, Arun V.,Sharma, Brijesh M.
, (2022/02/25)
This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask
Solar photo-thermochemical syntheses of 4-bromo-2,5-substituted oxazoles from N-arylethylamides
Dinda, Milan,Samanta, Supravat,Eringathodi, Suresh,Ghosh, Pushpito K.
, p. 12252 - 12256 (2014/03/21)
Solar photo-thermochemical C(sp3)-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.
