Preparation of new nitrogen-bridged heterocycles 67. syntheses of alpha,alpha'-Bis[(thieno[3,4-b]indolizin-3-yl)thio]-o-, m-, and p-xylene derivatives and their conformational structures.
The alkaline treatment and dehydrogenation of pyridinium salts, formed from the S-alkylations of 3-(1-pyridinio)thiophene-2-thiolates with alpha,alpha-dibromo-o-, m-, or p-xylene, provided the corresponding alpha,alpha'-bis[(thieno[3,4-b]indolizin-3-yl)thio]-o-, m-, and p-xylene derivatives in low to good yields. Both (1)H-NMR and UV-Vis spectra of these products supported distinctly the predominance of the gauche-gauche conformation in relation to the two sulfide linkages as the spacer in these molecules. On the other hand, the X-ray analyses indicated the expected gauche-gauche conformation for the m- and the p-xylene derivatives, but the anti-anti one for the o-xylene derivative.
Kakehi
Akikazu
A
Department of Chemistry and Material Engineering, Shinshu University, Wakasato, Nagano, Japan. xkakehi@ shinshu-u.ac.jp
Suga
Hiroyuki
H
Okumura
Yukihisa
Y
Shinohara
Masatoshi
M
Kako
Tomonao
T
Sekiguchi
Takeshi
T
Shiro
Motoo
M
D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D014992:Xylenes / Q000138:chemical synthesis* / Q000737:chemistry*
D006571:Heterocyclic Compounds; D007212:Indolizines; D013438:Sulfhydryl Compounds; D014992:Xylenes; C035094:indolizine; C031286:4-xylene; D009584:Nitrogen