Synthesis and Structure Characterization of Novel 3-Substituted-(thio)chroman-4-one Derivatives

doi:10.6023/cjoc1108011

Chin. J. Org. Chem. ›› 2012, Vol. ›› Issue (03): 608-611.DOI: 10.6023/cjoc1108011 Previous Articles Next Articles

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新型3-取代(硫)色满-4-酮衍生物的合成及其结构表征

吴利欢, 郭海福, 黄新仪, 吴瑞芬

肇庆学院化学化工学院肇庆 526060

收稿日期:2011-08-01 修回日期:2011-09-18 发布日期:2012-03-24
通讯作者: 吴利欢 E-mail:zqwlh@126.com
基金资助:
肇庆市科技创新计划(No. 2009G12)和广东省自然科学基金(No. 07010338)资助项目.

Synthesis and Structure Characterization of Novel 3-Substituted-(thio)chroman-4-one Derivatives

Wu Lihuan, Guo Haifu, Wang Xinyi, Wu Ruifen

School of Chemistry and Chemical Engineering, Zhaoqing University, Zhaoqing 526060

Received:2011-08-01 Revised:2011-09-18 Published:2012-03-24
Supported by:
Project supported by the Scientific and Technological Innovation of Zhaoqing City (No. 2009G12) and the Natural Science Foundation of Guangdong Province (No. 07010338).

A series of novel 3-substituted-(thio)chroman-4-one derivatives 3a～3l were synthesized by the condensation of substituted (unsubstituted)-(thio)chromanone with aromatic aldehydes in the presence of sodium hydroxide, via two different methods of conventional solvent method and solvent-free grinding method which has advantages of simple work-up procedure, shorter reaction time, milder conditions and environ-mental friendliness. The structures of the title compounds 3a～3l were characterized by IR, ¹H NMR, ¹³C NMR and MS techniques.

Key words: chromanone, solvent-free, grinding

Cite this article

Wu Lihuan, Guo Haifu, Wang Xinyi, Wu Ruifen . Synthesis and Structure Characterization of Novel 3-Substituted-(thio)chroman-4-one Derivatives[J]. Chin. J. Org. Chem., 2012, (03): 608-611.

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[1] Li, X.-L.; Wang, Y.-M.; Meng, J.-B.; Du, C.-P. Chin. J. Org. Chem.1998, 18(1), 20 (in Chinese).(李晓陆, 王永梅, 孟继本, 杜灿屏, 有机化学, 1998, 18(1), 20.)

[2] Loggia, R. D.; Negro, P. D.; Tubaro, A.; Barone, G.; Parrilli, M.Planta Med. 1989, 55(6): 587

[3] Likhitwitayawuid, K.; Sawasdee, K.; Kirtikara, K. Planta Med.2002, 68, 8413.

[4] Fisher, M. J.; Happ, A. M.; Jakubowski, J. A.; Kinnick, M. D.;Kline, A. D.; Martinelli, M. J.; Morin, J. J. M.; Paal, M.; Ruhter, G.;Ruterbories, K. J.; Sall, D. J.; Schotten, T.; Skelton, M. A.; Stenzel,W.; Vasileff, R. T. US 6448269, 2002 [Chem. Abstr. 1997, 126,330553].

[5] Bikker, J.; Dobrusin, E. M.; Doherty, A. M.; Drowns, M.; Kaltenbronn,J. S.; Kleinschroth, J.; McNamara, D. J.; Quin, J.; Repine, J.T.; Stasiak, M. US 6528535, 2003 [Chem. Abstr. 1998, 129,175640].

[6] Perjési, P.; Das, U.; De, Clercq E.; Balzarini, J.; Kawase, M.; Sakagami,H.; Lorand, T.; Rozmer, Z.; Dimmock, J. R. Eur. J. Med.Chem. 2008, 43(4), 839.

[7] Nakib, A. T.; Bezjak, V.; Meegan, M. J.; Chandy, R. Eur. J. Med.Chem. 1990, 25(5), 455.

[8] Xu, P.; Jin, Y.-H.; Guo, C.; Fang, L. Chin. J. Med. Chem. 2003,13(3), 134 (in Chinese).(齐平, 靳颖华, 郭春, 方林, 中国药物化学杂志, 2003, 13(3),134.)

[9] Tramontini, M.; Angiolini, L. Tetrahedron 1990, 46(6), 1791.

[10] Wu, L.-H.; Guo, H.-F.; Li, S.-H. Guangdong Chem. Ind. 2007,34(1), 91 (in Chinese).(吴利欢, 郭海福, 李顺华, 广东化工, 2007, 34(1), 91.)

[11] Hu, S.-G.; Chen, J.-D.; Jian, J.-X. Chin. J. Pharmaceut. 1990,21(5): 220-223.)(胡水根, 陈健东, 蒋继新. 中国医药工业杂志, 1990, 21(5),220～223.)

[12] Wu, L.-H.; Lin, Z.-H.; Cai, L.-Q. Fine Chem. Intermediates 2010,40(2), 38 (in Chinese).(吴利欢, 林真辉, 蔡立琼, 精细化工中间体, 2010, 40(2), 38.)

[13] Hurd, C. D.; Shin, H. J. Am. Chem. Soc., 1954, 76(20), 5065.

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新型3-取代(硫)色满-4-酮衍生物的合成及其结构表征

Synthesis and Structure Characterization of Novel 3-Substituted-(thio)chroman-4-one Derivatives

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