1214922-06-1Relevant articles and documents
Single-Step Synthesis of Iodinated Oxazoles from N-Propargyl Amides Mediated by I2/Iodosylbenzene/Trimethylsilyl Trifluoromethanesulfonate Systems
Suzuki, Sho,Saito, Akio
, p. 11859 - 11864 (2017)
A combination of I2, iodosylbenzene, and trimethylsilyl trifluoromethanesulfonate (TMSOTf) is effective for single-step synthesis of iodinated oxazoles from N-propargyl amides via the aromatization of the iodocyclized intermediates, which has difficulty proceeding through conventional iodocyclization methods. Compared to the former method consisting of the metal-catalyzed cyclization of N-propargyl amides followed by halogenation of alkylideneoxazolines, the present reaction provides a facile and metal-free procedure.
Cyclization of propargylic amides: Mild access to oxazole derivatives
Weyrauch, Jan P.,Hashmi, A. Stephen K.,Schuster, Andreas,Hengst, Tobias,Schetter, Stefanie,Littmann, Anna,Rudolph, Matthias,Hamzic, Melissa,Visus, Jorge,Rominger, Frank,Frey, Wolfgang,Bats, Jan W.
supporting information; experimental part, p. 956 - 963 (2010/06/12)
The substrate scope, the mechanistic aspects of the gold-catalyzed oxazole synthesis, and substrates with different aliphatic, aromatic, and functional groups in the side chain were investigated. Even molecules with several propargyl amide groups could easily be converted, delivering di- and trioxazoles with interesting optical properties. Furthermore, the scope of the gold(I)-catalyzed alkylidene synthesis was investigated. Further functionalizations of these isolable intermediates of the oxazole synthesis were developed and chelate ligands can be obtained. The use of Barluenga's reagent offers a new and mild access to the synthetically valuable iodoalkylideneoxazoles from propargylic amides, this reagent being superior to other sources of halogens.
