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Novel Synthesis of 4H-Quinolizine Derivatives Using Sulfonyl Ketene Dithioacetals

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Title: Novel Synthesis of 4H-Quinolizine Derivatives Using Sulfonyl Ketene Dithioacetals
Authors: Hagimori, Masayori / Matsui, Sayaka / Mizuyama, Naoko / Yokota, Kenichirou / Nagaoka, Junko / Tominaga, Yoshinori
Issue Date: Nov-2009
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry, 2009(33), pp.5847-5853; 2009
Abstract: 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.
Keywords: Nitrogen heterocycles / Sulfur / Fluorescence / Organic light-emitting ­diodes
URI: http://hdl.handle.net/10069/22620
ISSN: 1434193X
DOI: 10.1002/ejoc.200900783
Rights: Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim / 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.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/22620

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