Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides: First Isolation of Oxyselenuranes [10-Se-4(C3O)] as a Reaction Intermediate

Tadashi Kataoka; Shin-ichi Watanabe Si; Keiichirou Yamamoto; Mitsuhiro Yoshimatsu; Genzoh Tanabe; Osamu Muraoka

doi:10.1021/jo980999x

Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides: First Isolation of Oxyselenuranes [10-Se-4(C3O)] as a Reaction Intermediate

J Org Chem. 1998 Sep 4;63(18):6382-6386. doi: 10.1021/jo980999x.

Authors

Tadashi Kataoka¹, Shin-ichi Watanabe Si, Keiichirou Yamamoto, Mitsuhiro Yoshimatsu, Genzoh Tanabe, Osamu Muraoka

Affiliation

¹ Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan, Faculty of Education, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan, and Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.

PMID: 11672273
DOI: 10.1021/jo980999x

Abstract

The reaction of the diphenyl(phenylethynyl)selenonium triflate 1a with active methylene compounds 5 and t-BuOK in THF gave furan derivatives 6. The [10-Se-4(C3O)] selenuranes 8a and 8b could be isolated from the reactions with benzoylacetonitrile 5f and with 1,3-indandione 5g, respectively, as reaction intermediates. The structures of the selenuranes 8 were elucidated by X-ray crystallography and (77)Se high-resolution solid-state NMR spectroscopy. The selenuranes 8 underwent ligand coupling on standing at room temperature or refluxing in chloroform and gave the furan derivatives 6 and the ring-opened product 9. Similarly, the reaction of 1a with benzamide 13a and pivalamide 13d in the presence of NaH in THF afforded oxazole derivatives 14.