Alpha-sulfanyl and alpha-selanyl propadienyl cations: regioselective generations and cycloadditions with thioamides and selemides controlled by MeNO2-H2O system.
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.
Yoshimatsu
Mitsuhiro
M
Department of Chemistry, Faculty of Education, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan. yoshimae@gifu-u.ac.jp
Yamamoto
Teruhisa
T
Sawa
Arisa
A
Kato
Tomohiro
T
Tanabe
Genzoh
G
Muraoka
Osamu
O
D002384:Catalysis; D002412:Cations; D003500:Cyclization; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D012538:Scandium / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013854:Thioamides / Q000737:chemistry*
D002412:Cations; D008698:Mesylates; D016566:Organoselenium Compounds; D013438:Sulfhydryl Compounds; D013844:Thiazoles; D013854:Thioamides; C436603:scandium triflate; D012538:Scandium