SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 08: 1547 - 1551

DOI: https://doi.org/10.6023/cjoc1112301

研究简报

萘基薁并[2,1-d]嘧啶-4-胺类衍生物的合成

  • 王道林 ,
  • 于家懿 ,
  • 李伟 ,
  • 崔庆涛 ,
  • 冯姗姗
展开
  • 渤海大学化学化工与食品安全学院 辽宁省功能化合物合成与应用重点实验室 锦州 121003

收稿日期: 2011-12-30

  修回日期: 2012-03-01

  网络出版日期: 2012-04-11

基金资助

辽宁省科技厅(No. 2011220022)资助项目.

收起

Synthesis of Naphthylazuleno[2,1-d]pyrimidin-4-amines

  • Wang Daolin ,
  • Yu Jiayi ,
  • Li Wei ,
  • Cui Qingtao ,
  • Feng Shanshan
Expand
  • Key Laboratory of Synthesis & Application of Functional Compound, College of Chemistry, Chemical Engineering & Food Safety, Bohai University, Jinzhou 121003

Received date: 2011-12-30

  Revised date: 2012-03-01

  Online published: 2012-04-11

Supported by

Project supported by the Science and Technology Department of Liaoning Province (No. 2011220022).

Fold

摘要

研究了萘基薁并[2,1-d]嘧啶-4-胺类衍生物的合成方法. 以托酚酮、萘乙酸乙酯、N,N-二甲基甲酰胺二甲缩醛(DMF-DMA)及芳香胺为原料, 依次经过氯代、缩合、环加成、环化反应得到目标产物. 该反应操作简单、条件温和、收率良好. 产物的结构经1H NMR, IR及元素分析等得以证实.

关键词： 薁; 薁并[2,1-d]嘧啶; 萘乙酸乙酯; N,N-二甲基甲酰胺二甲缩醛(DMF-DMA); 芳香胺; 合成

本文引用格式

王道林 , 于家懿 , 李伟 , 崔庆涛 , 冯姗姗 . 萘基薁并[2,1-d]嘧啶-4-胺类衍生物的合成[J]. 有机化学, 2012 , 32(08) : 1547 -1551 . DOI: 10.6023/cjoc1112301

Abstract

In this paper, a synthetic method for naphthylazuleno[2,1-d]pyrimidin-4-amines was reported, which began from cheap tropolone, ethyl naphthaleneacetate, malononitrile N,N-dimethylformamide dimethyl acetal (DMF-DMA) and anilines, followed by chlorination, condensation, cyclization and then Dimroth rearrangement reaction, to give naphthylazuleno[2,1-d]pyrimidin-4-amines in moderate yields. The structures of synthesized compounds were determined by 1H NMR, IR spectra and elemental analysis. This method provides several advantages such as good yield and simple work-up procedure.

Key words： azulene; azuleno[2,1-d]pyrimidine; ethyl naphthaleneacetate; DMF-DMA; aniline; synthesis

参考文献

[1] MeGuire, J. J. Curr. Pharm. Des. 2003, 9, 2593.

[2] Baraldi, P. G.; Caceiari, B.; Rorllagnoli, R.; Merighi, S.; Varani, K.; Borea, P. A.; Spalluto, G. Med. Res. Rev. 2000, 20, 103.

[3] Bridges, A. J. Chem. Rev. 2001, 101, 2541.

[4] Berger, M.; Albrecht, B.; Berces, A.; Ettmayer, P.; Neruda, W.; Woisetschlager, M. J. Med. Chem., 2001, 44(18), 3031.

[5] Ravi Kanth, S.; Venkat Reddy, G.; Hara Kishore, K.; Shanthan Rao, P.; Narsaiah, B.; Surya Narayana Murthy, U. Eur. J. Med. Chem. 2006, 41, 1011.

[6] Frank. S.; Matthias, Z.; Markus, S.; Michael, D. Helv. Chim. Acta 2000, 83, 910.

[7] Munchhof, M. J.; Beebe, J. S.; Casavant, J. M.; Cooper, B. A.; Doty, J. L.; Higdon, R. C.; Hillerman, S. M.; Soderstrom, C. I.; Knauth, E. A.; Marx, M. A.; Rossi, A. M. K.; Sobolov, S. B.; Sun, J. Bioorg. Med. Chem. Lett. 2004, 14, 21.

[8] (a) Matsuno, K.; Seishi, T.; Nakajima, T.; Ichimura, M.; Giese, N. A.; Yu, J. C.; Oda, S.; Nomoto, Y. Bioorg. Med. Chem. Lett. 2003, 13, 3001.(b) Peng, J. S.; Lin, W. Q.; Jiang, D. H.; Yuan, S. X.; Chen. Y. W. J. Comb. Chem. 2007, 9, 431

[9] Santagada, V.; Perissutti, E.; liendo, G. Curr. Med. Chem. 2002, 9, 1251.

[10] Yanagisawa, T.; Wakabayashi, S.; Tomiyama, T.; Yasunami, M.; Takase, K. Chem. Pharm. Bull. 1988, 36, 641.

[11] (a) Asato, A. E.; Peng, A.; Hossain, M. Z.; Mirzadegan, T.; Bertram, J. J. Med. Chem. 1993, 36, 3137.(b) Hong, B. C.; Jiang, Y. F.; Kumar, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 1981.

[12] Becker, D. A.; Ley, J. J.; Echegoyen, L.; Alvarado, R. J. Am. Chem. Soc. 2002, 124, 4678.

[13] (a) Fisher, G. Advances in Heterocyclic Chemistry, Ed.: Katritzky, A. R., Academic Press, New York, 1995, 64, p. 81.(b) Fisher, G. Advances in Heterocyclic Chemistry, Ed.: Katritzky, A. R., Academic Press, New York, 1996, 66, p. 285.

[14] (a) Wang, D. L.; Xu, J.; Han, S.; Gu, Z. Chin. J. Org. Chem. 2007, 27, 1305 (in Chinese).(王道林, 徐姣, 韩珊, 谷峥, 有机化学, 2007, 27, 1305.)(b) Imafuku, K.; Wang, D. L. Heterocycles 2002, 58, 405.(c) Wang, D. L.; Imafuku, K. Heterocycles 2001, 54, 647.

[15] (a) Wang, D. L.; Xu, J.; Gu, Z.; Han, S. Chin. J. Org. Chem. 2007, 27, 1404 (in Chinese).(王道林, 徐姣, 谷峥, 韩珊, 有机化学, 2007, 27, 1404.)(b) Wang, D. L.; Den, J. J.; Xu, J.; Gu, Z.; Han, S.; Imafuku, K. Heterocycles 2007, 71, 2237. (c) Wang, D. L.; Imafuku, K. J. Heterocycl. Chem. 2004, 41, 723.

[16] Wang, D. L.; Han, S.; Gu, Z.; Xu, J. Chin. J. Org. Chem. 2008, 28, 1641 (in Chinese).(王道林, 韩珊, 谷峥, 徐姣, 有机化学, 2008, 28, 1641.)

[17] (a) Sun, S. G.; Gu, Z.; Wang, D. L.; Han, S.; Huang, X. D. Chin. J. Org. Chem. 2009, 29, 2012 (in Chinese).(孙曙光, 谷峥, 王道林, 韩珊, 黄孝东, 有机化学, 2009, 29, 2012.)(b) Wang, D. L.; Lin, L. N.; Li, S. F.; Li, W.; Li, Y. F. Chin. J. Org. Chem. 2010, 30, 1774 (in Chinese).(王道林, 林力男, 李少飞, 李伟, 李元峰, 有机化学, 2010, 30, 1774.)

[18] Wang, D. L.; Gu, Z.; Xu, J.; Han, S.; Imafuku, K. Synth. Commun. 2009, 39, 2329.

[19] Noze, T.; Takase, K.; Nakazawa, T.; Fukuta, S. Tetrahedron 1971, 27, 3357.

[20] Chandregowda, V.; Rao, G. V.; Reddy, G. C. Org. Process Res. Dev. 2007, 11, 813.
Options
文章导航

/

〈 〉