Palladium-catalyzed denitrogenation reaction of 1,2,3-benzotriazin-4(3H)-ones incorporating isocyanides

Tomoya Miura; Yui Nishida; Masao Morimoto; Motoshi Yamauchi; Masahiro Murakami

doi:10.1021/ol103143a

Palladium-catalyzed denitrogenation reaction of 1,2,3-benzotriazin-4(3H)-ones incorporating isocyanides

Org Lett. 2011 Mar 18;13(6):1429-31. doi: 10.1021/ol103143a. Epub 2011 Feb 14.

Authors

Tomoya Miura¹, Yui Nishida, Masao Morimoto, Motoshi Yamauchi, Masahiro Murakami

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.

PMID: 21319832
DOI: 10.1021/ol103143a

Abstract

1,2,3-Benzotriazin-4(3H)-ones and 1,2,3,4-benzothiatriazine 1,1(2H)-dioxide reacted with isocyanides in the presence of a palladium catalyst to give 3-(imino)isoindolin-1-ones and 3-(imino)thiaisoindoline 1,1-dioxides, respectively, in high yield. An intermediate azapalladacycle was generated through denitrogenation of the triazine moiety, and an isocyanide was incorporated therein.