20771-08-8Relevant academic research and scientific papers
O-Transfer-facilitated cyclizations of propargylamides with TMSN3: Selective synthesis of tetrazoles and dihydroimidazoles
Hu, Yancheng,Yi, Ruxia,Yu, Xinzhang,Xin, Xiaoyi,Wang, Chunxiang,Wan, Boshun
supporting information, p. 15398 - 15401 (2015/10/20)
An unprecedented formal [3+2] annulation of propargylamides with TMSN3 to deliver functionalized tetrazoles is developed. Oxygen-atom transfer (OAT) from the amide group to the CC bond was realized via a NIS-triggered-cyclization/ring-opening cascade pathway. The OAT process enables the amide to serve as a two-atom unit in the reactions. Notably, in situ umpolung of azide occurred when terminal propargylamides were employed in this reaction, providing an array of diiodomethylated dihydroimidazoles.
Thermal rearrangement of azido ketones into oxazoles via azirines: One-pot, metal-free heteroannulation to functionalized 1,3-oxazoles
Shah, Shailesh R.,Navathe, Sudhanva S.,Dikundwar, Amol G.,Guru Row, Tayur N.,Vasella, Andrea T.
supporting information, p. 264 - 267 (2013/02/26)
α-Azidoacetophenones were converted into 2-aryl-1,3-oxazole-4- carbaldehydes through rearrangement of the carbon framework upon exposure to DMF/POCl3. The unprecedented rearrangement occurs via alkenyl azides and 2H-azirines. A mechanism for this unusual reaction was proposed and evidenced.
A flexible synthetic approach to the hennoxazoles
Zylstra, Eric J.,She, Miles W.-L.,Salamant, Walter A.,Leahy, James W.
, p. 623 - 627 (2007/10/03)
Three advanced intermediates corresponding to the carbon skeleton of the hennoxazoles have been prepared. Central to the strategy is the synthesis of the oxazoles prior to coupling with the other fragments and a dithiane addition to allow for the generati
