127978-78-3Relevant articles and documents
Exocyclic N-Acyliminium Ion (NAI) Cyclization: Access to Fully Substituted Oxazoles and Furocoumarins
Babu, Venkata Nagarjuna,Murugan, Arumugavel,Katta, Narenderreddy,Devatha, Suman,Sharada, Duddu S.
, p. 6631 - 6641 (2019/06/07)
A concise, one-pot route to oxazoles and furocoumarins has been reported. The key step in this transformation involves in situ generation of N-acyliminium ion (NAI) precursor under catalyst and solvent-free conditions and their further transformations promoted by superacid in the same pot. We have also presented the experimental evidence for the involvement of proto-solvated novel exocyclic N-acyliminium ion. Further, the UV-visible and fluorescence studies revealed that few of the compounds reported here exhibited emission of blue light upon irradiation in EtOH in the region of 404-422 nm.
Synthesis of α-keto-imides via oxidation of ynamides
Al-Rashid, Ziyad F.,Johnson, Whitney L.,Hsung, Richard P.,Wei, Yonggang,Yao, Pei-Yuan,Liu, Renhei,Zhao, Kang
supporting information; experimental part, p. 8780 - 8784 (2009/04/11)
(Chemical Equation Presented) A de novo preparation of α-keto-imides via ynamide oxidation is described. With a number of alkyne oxidation conditions screened, a highly efficient RuO2-NaIO4 mediated oxidation and a DMDO oxidation have been identified to tolerate a wide range of ynamide types. In addition to accessing a wide variety of α-keto-imides, the RuO2-NaIO4 protocol provides a novel entry to the vicinal tricarbonyl motif via oxidation of push-pull ynamides, and imido acylsilanes from silyl-substituted ynamides. Chemoselective oxidation of ynamides containing olefins can be achieved by using DMDO, while the RuO 2-NaIO4 protocol is not effective. These studies provide further support for the synthetic utility of ynamides.