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.
Kakehi
Akikazu
A
Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano, Japan. akakehi@gipwc.shinshu-u.ac.jp
Suga
Hiroyuki
H
Kako
Tomonao
T
Fujii
Tsuneo
T
Tanaka
Nobuaki
N
Kobayashi
Tomoshige
T
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