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Synthesis, solid-state fluorescence properties, and computational analysis of novel 2-aminobenzo[4,5]thieno[3,2-d]pyrimidine 5,5-dioxides


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Title: Synthesis, solid-state fluorescence properties, and computational analysis of novel 2-aminobenzo[4,5]thieno[3,2-d]pyrimidine 5,5-dioxides
Authors: Yokota, Kenichirou / Hagimori, Masayori / Mizuyama, Naoko / Nishimura, Yasuhisa / Fujito, Hiroshi / Shigemitsu, Yasuhiro / Tominaga, Yoshinori
Issue Date: 16-Feb-2012
Publisher: Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
Citation: Beilstein Journal of Organic Chemistry, 8, pp.266-274; 2012
Abstract: New fluorescent compounds, benzo[4,5]thieno[3,2-d]pyrimidine 5,5-dioxides (3a-g), 2-amino-4-methylsulfanylbenzo[4,5]thieno[3,2-d]pyrimidine (6), and 2-amino-4-methylsulfanyl-7-methoxybenzo[4,5]furo[3,2-d]pyrimidine (7), were synthesized in good yields from heterocyclic ketene dithioacetals (1a-c) and guanidine carbonate (2a) or (S)-methylisothiourea sulfate (2b) in pyridine under reflux. Among the fused pyrimidine derivatives, compound 3c, which has an amino group at the 2-position and a benzylamino group at the 4-position of the pyrimidine ring, showed the strongest solid-state fluorescence. The absorption and emission properties of the compounds were quantitatively reproduced by a series of ab initio quantum-chemical calculations.
Keywords: Amino group / Fluorescence / HOMO/LUMO / Pyrimidine / Solid-state
URI: http://hdl.handle.net/10069/28989
DOI: 10.3762/bjoc.8.28
Rights: © 2012 Yokota et al; licensee Beilstein-Institut. / This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
Type: Journal Article
Text Version: publisher
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/28989

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