433211-65-5Relevant academic research and scientific papers
Preparation of new nitrogen-bridged heterocycles. 53. Syntheses of 3-(benzylthio)thieno[3,4-b]indolizine derivatives and their intramolecular arene-arene interactions.
Kakehi, Akikazu,Ito, Suketaka,Suga, Hiroyuki,Miwa, Takeyuki,Mori, Takashi,Fujii, Tsuneo,Tanaka, Nobuaki,Kobayashi, Tomoshige
, p. 75 - 84 (2007/10/03)
Various ethyl 1-arylcarbonyl-3-[(un)substituted methylthio]thieno[3,4-b]indolizine-9-carboxylates were synthesized in good yields by a novel methodology in which the S-alkylation of 5-arylcarbonyl-4-ethoxycarbonylmethyl-3-(1-pyridinio)thiophene-2-thiolates with alkyl or benzyl halides, the 1,5-dipolar cyclization of the resulting pyridinium salts in the presence of a base, and the aromatization were performed. In the X-ray analyses of some 3-(benzylthio)thieno[3,4-b]indolizine-9-carboxylates, a gauche and two anti conformers in relation to the exocyclic sulfide linkage were found. Interestingly, all of the 3-(benzylthio)thieno[3,4-b]indolizine derivatives showed significant high-field shifts (delta up to 0.3 ppm) for the 5- and 6-proton signals compared with those of the 3-methylthio derivatives in the (1)H-NMR spectra and exhibited a definite absorption band near 425 nm in their UV spectra, indicating an intramolecular arene-arene interaction between the thieno[3,4-b]indolizine and the phenyl ring.
A through-space interaction of 3-benzylthiothieno-[3,4-b]indolizine derivatives combined by a highly flexible spacer
Kakehi, Akikazu,Ito, Suketaka,Suga, Hiroyuki,Miwa, Takeyuki,Mori, Takashi,Kobayashi, Tomoshige
, p. 17 - 20 (2007/10/03)
Some ethyl 1-benzoyl-3-[(un)substituted benzylthio]thieno-[3,4-b]indolizine-9-carboxylates were prepared and their conformations were investigated. In the solid state and the chloroform solution they had stacked structures in which the phenyl ring and the pyridine moiety of theino[3,4-b]indolizine ring are partly overlapped.
