Preparation of new nitrogen-bridged heterocycles. 54.increased arene-arene interactions of 3-(bicyclic and tricyclic arylmethylthio)thieno[3,4-b]indolizine derivatives.
Some thieno[3,4-b]indolizine derivatives having a 1-naphthylmethylthio, 2-methyl-1-naphthylmethylthio, 2-naphthylmethylthio, or 9-anthrylmethylthio group at the 3-position were prepared and their intramolecular arene-arene interactions were investigated. In comparison with 3-(methylthio)thieno[3,4-b]indolizines which have no such interactions, the (1)H-NMR spectra of title compounds showed large high-field shifts (delta 0.06-0.89 ppm) for the protons of the pyridine ring in the thieno[3,4-b]indolizine, and these values were considerably larger than those (delta <0.3 ppm) in 3-(benzylthio)thieno[3,4-b]indolizines. The UV spectra also exhibited a characteristic absorption band near 425 nm attributable to the arene-arene interaction. In the X-ray analyses of some compounds, however, the presence of both the gauche and the anti conformers at the sulfide spacer were confirmed.
Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano, Japan. akakehi@gipwc.shinshu-u.ac.jp
Akikazu
A
Kakehi
Hiroyuki
H
Suga
Tomonao
T
Kako
Tsuneo
T
Fujii
Nobuaki
N
Tanaka
Tomoshige
T
Kobayashi
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007202:Indicators and Reagents; D007212:Indolizines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D007212:Indolizines