Rhodium(II)-catalyzed annulation of N-sulfonyl1,2,3-triazoles with 1,3,5-triazinanes to produce octahydro-1H-purine derivatives: a combined experimental and computational study

Jiemin Ge, Xueli Wu and Xiaoguang Bao ^*（鲍晓光）

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China

Chem. Commun., 2019, 55, 6090--6093

The Rh(II)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with 1,3,5-triazinanes leading to the octahydro-1H-purine derivatives with moderate to good yields is described in this communication. Mechanistic studies via DFT calculations suggest that the 1,3,5-triazinanes might undergo a formal [6+3] cycloaddition with the Rh(II)-azavinyl carbene intermediates, which are generated from Rh(II)-catalyzed denitrogenation of 1,2,3-triazoles. Afterwards, ring-closure of the formed nine-membered ring intermediate via intramolecular nucleophilic addition followed by subsequent rearrangements could afford the final octahydro-1H-purine derivatives.

链接：https://pubs.rsc.org/en/content/articlelanding/2019/CC/C9CC02294E#!divAbstract