Alpha-sulfanyl and alpha-selanyl propadienyl cations: regioselective generations and cycloadditions with thioamides and selemides controlled by MeNO2-H2O system

Mitsuhiro Yoshimatsu; Teruhisa Yamamoto; Arisa Sawa; Tomohiro Kato; Genzoh Tanabe; Osamu Muraoka

doi:10.1021/ol9011844

Alpha-sulfanyl and alpha-selanyl propadienyl cations: regioselective generations and cycloadditions with thioamides and selemides controlled by MeNO2-H2O system

Org Lett. 2009 Jul 2;11(13):2952-5. doi: 10.1021/ol9011844.

Authors

Mitsuhiro Yoshimatsu¹, Teruhisa Yamamoto, Arisa Sawa, Tomohiro Kato, Genzoh Tanabe, Osamu Muraoka

Affiliation

¹ Department of Chemistry, Faculty of Education, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. yoshimae@gifu-u.ac.jp

PMID: 19505122
DOI: 10.1021/ol9011844

Abstract

Alpha-sulfanyl and alpha-selanyl propadienyl cations were easily generated by the catalytic system, scandium triflate-nitromethane-H(2)O in the presence of Bu(4)NHSO(4), to regioselectively afford the multifunctionalized thiazoles and selenazoles in high yields.

MeSH terms

Catalysis
Cations
Cyclization
Mesylates / chemistry
Molecular Structure
Organoselenium Compounds / chemical synthesis
Organoselenium Compounds / chemistry*
Scandium / chemistry
Stereoisomerism
Sulfhydryl Compounds / chemistry*
Thiazoles / chemical synthesis*
Thiazoles / chemistry
Thioamides / chemistry*

Substances

Cations
Mesylates
Organoselenium Compounds
Sulfhydryl Compounds
Thiazoles
Thioamides
scandium triflate
Scandium