Synthesis of Bridged Azacycles and Propellanes via Nitrene/Alkyne Cascades was written by Wang, Qinxuan;May, Jeremy A.. And the article was included in Organic Letters in 2020.Safety of 1-Tosylpiperidin-4-one This article mentions the following:
A nitrene/alkyne cascade reaction terminating in C-H bond insertion to form functionalized bridged azacycles from carbonazidates is presented. Due to an initial Huisgen cyclization, all carbonazidates reacted with the alkyne in an exo mode in contrast to the use of sulfamate esters, which react predominately in an endo mode. Substrates with different ring sizes as well as different aryl and heteroaryl groups were also explored. Variation of the nitrene tether showed that 7-membered rings were the maximum ring size to be formed by nitrene attack on the alkyne. Examples incorporating stereocenters on the carbonazidate’s tether induced diasteroselectivity in the formation of the bridged ring and two new stereocenters. Addnl., propellanes containing aminals, hemiaminals, and thioaminals formed from the bridged azacycles in the same reaction via an acid-promoted rearrangement. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Safety of 1-Tosylpiperidin-4-one).
1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Safety of 1-Tosylpiperidin-4-one
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem