Platinum-catalyzed dehydroalkoxylation-cyclization cascade via N-O bond cleavage

Itaru Nakamura; Yusuke Sato; Masahiro Terada

doi:10.1021/ja900174t

Platinum-catalyzed dehydroalkoxylation-cyclization cascade via N-O bond cleavage

J Am Chem Soc. 2009 Apr 1;131(12):4198-9. doi: 10.1021/ja900174t.

Authors

Itaru Nakamura¹, Yusuke Sato, Masahiro Terada

Affiliation

¹ Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. itaru-n@mail.tains.tohoku.ac.jp

PMID: 19267436
DOI: 10.1021/ja900174t

Abstract

ortho-Alkynylphenylureas and -acetamides 1, with an alkoxy and aryl group on the nitrogen atom, were subjected to platinum-catalyzed cyclization reactions to afford the corresponding tetracyclic compounds 2, via N-O bond cleavage, in good to excellent yields. For example, N-methoxy-N'-methyl-N'-(2-(pent-1-ynyl)phenyl)-N-phenylurea (1a) was reacted for 12 h in the presence of PtI(4) (10 mol%) in 1,4-dioxane at 100 degrees C to afford 5-methyl-12-propylindolo[1,2-c]quinazolin-6(5H)-one (2a) in 93% yield, via an iminium-bound platinum carbenoid intermediate, followed by an aromatic C-H insertion.