Preparation of New Nitrogen-Bridged Heterocycles. 53. Syntheses of 3-(Benzylthio)thieno[3,4-b]indolizine Derivatives and Their Intramolecular Arene-Arene Interactions.
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Accession number;03A0040962
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| Title;Preparation of New Nitrogen-Bridged Heterocycles. 53. Syntheses of 3-(Benzylthio)thieno[3,4-b]indolizine Derivatives and Their Intramolecular Arene-Arene Interactions. |
| Author;
KAKEHI A
(Shinshu Univ., Nagano, Jpn)
ITO S
(Shinshu Univ., Nagano, Jpn)
SUGA H
(Shinshu Univ., Nagano, Jpn)
MIWA T
(Shinshu Univ., Nagano, Jpn)
MORI T
(Shinshu Univ., Nagano, Jpn)
FUJII T
(Shinshu Univ., Nagano, Jpn)
TANAKA N
(Shinshu Univ., Nagano, Jpn)
KOBAYASHI T
(Shinshu Univ., Matsumoto, Jpn)
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Journal Title;Chem Pharm Bull
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Journal Code:G0504A
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ISSN:0009-2363
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VOL.51;NO.1;PAGE.75-84(2003)
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| Figure&Table&Reference;FIG.7, TBL.3, REF.9 |
| Pub. Country;Japan |
| Language;English |
| Abstract;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 1H-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. (author abst.) |
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