Preparation of New Nitrogen-Bridged Heterocycles. 58. : Syntheses and Intramolecular Arene-π Interactions of 3-(Allylthio)- and 3-(Propargylthio)thieno[3,4-b]indolizine Derivatives

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Various thieno[3, 4-b]indolizine derivatives having an allylthio or propargylthio group at the 3-position were prepared and their intramolecular arene-π interactions were investigated. Their ^1H-NMR spectra showed significant low-field shifts (δ0.10-0.34ppm) to the 5-proton on the thieno[3, 4-b]indolizine ring, and this effect was the reverse to that observed in 3-(arylmethylthio)thieno[3, 4-b]indolizines. However, their UV spectra exhibited a characteristic absorption band due to the arene-π interaction near 430nm and these values were almost similar to those for arene-arene interaction of 3-arylmethylthio derivatives though their molar extinction coefficients were largely varied by the 3-substituents. Furthermore, both types of gauche conformations in which the intramolecular arene-π interactions are possible in one form and impossible in the other were confirmed by X-ray analyses of some compounds.
公益社団法人日本薬学会の論文
2005-11-01