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Novel Synthesis of 4H-Quinolizine Derivatives Using Sulfonyl Ketene Dithioacetals
http://hdl.handle.net/10069/22620
http://hdl.handle.net/10069/22620e6f90eb7-e389-4529-a17d-10a141416bcb
名前 / ファイル | ライセンス | アクション |
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EJOC33_5847.pdf (340.7 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2009-12-09 | |||||
タイトル | ||||||
タイトル | Novel Synthesis of 4H-Quinolizine Derivatives Using Sulfonyl Ketene Dithioacetals | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Nitrogen heterocycles | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Sulfur | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Fluorescence | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Organic light-emitting -diodes | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Hagimori, Masayori
× Hagimori, Masayori× Matsui, Sayaka× Mizuyama, Naoko× Yokota, Kenichirou× Nagaoka, Junko× Tominaga, Yoshinori |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | In the synthesis of 4H-quinolizine derivatives involving the use of a sulfonyl ketene dithioacetal, we found a novel reaction in which the remaining methylsulfanyl group was replaced with a proton after the ring-closure reaction in the quinolizine skeleton under mild conditions, without the use of any metallic reagent. The reaction of 3,3-bis(methylsulfanyl)-2-phenylsulfonylacrylonitriles (1a,b) with 2-pyridylacetonitrile (2a) in the presence of potassium carbonate as a base in DMSO afforded 4-imino-2-methylsulfanyl-3-phenylsulfonyl-4H-quinolizine-1-carbonitriles (3a,b). The methylsulfanyl group at the 2-position of 3a,b was readily removed under methanol reflux conditions to afford 4-imino-3-phenylsulfonyl-4H-quinolizine-1-carbonitriles (4a,b) in good yields. Alkyl 3-phenylsulfonyl-4H-quinolizine-1-carboxylates (4c-f) were directly synthesized from sulfonyl ketene dithioacetal (1a,b) with alkyl 2-pyridylacetates (2b,c) and involved desulfanylation by simple hydrolysis. In addition, the fluorescent properties of these compounds were investigated. | |||||
書誌情報 |
European Journal of Organic Chemistry 巻 2009, 号 33, p. 5847-5853, 発行日 2009-11 |
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出版者 | ||||||
出版者 | Wiley-VCH Verlag GmbH & Co. KGaA | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 1434193X | |||||
書誌レコードID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AA1118165X | |||||
DOI | ||||||
関連タイプ | isVersionOf | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.1002/ejoc.200900783 | |||||
権利 | ||||||
権利情報 | Copyright c 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim | |||||
権利 | ||||||
権利情報 | This is the pre-peer reviewed version of the following article: European Journal of Organic Chemistry, 2009(33), pp.5847-5853; 2009, which has been published in final form at http://www3.interscience.wiley.com/journal/122613631/abstract. | |||||
著者版フラグ | ||||||
出版タイプ | AM | |||||
出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | European Journal of Organic Chemistry, 2009(33), pp.5847-5853; 2009 |