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
| Autor: | Masatoshi Shinohara, Tomonao Kako, Hiroyuki Suga, Akikazu Kakehi, Motoo Shiro, Takeshi Sekiguchi, Yukihisa Okumura |
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| Rok vydání: | 2009 |
| Předmět: |
chemistry.chemical_classification
Magnetic Resonance Spectroscopy Molecular Structure Sulfide Nitrogen Stereochemistry Indolizines Molecular Conformation chemistry.chemical_element Thio General Chemistry General Medicine Xylenes Crystallography X-Ray p-Xylene chemistry.chemical_compound chemistry Heterocyclic Compounds Drug Discovery Molecule Dehydrogenation Sulfhydryl Compounds Pyridinium |
| Zdroj: | Chemical and Pharmaceutical Bulletin. 57:1385-1390 |
| ISSN: | 1347-5223 0009-2363 |
| DOI: | 10.1248/cpb.57.1385 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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