Zirconium-mediated Selective Synthesis of Quinoline Derivatives

doi:10.1007/s40242-016-6021-x

高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (4): 621-624.doi: 10.1007/s40242-016-6021-x

Zirconium-mediated Selective Synthesis of Quinoline Derivatives

MEN Yican¹, ZHANG Jiqian², ZHOU Lishan³, LI Junqiu¹, LIU Jun¹, LI Juan¹, QU Hongmei¹

1. Key Laboratory of Systems Bioengineering, Ministry of Education, Tianjin Key Laboratory of Biological and Pharmaceutical Engineering, Department of Pharmaceutical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China;
2. Nantong Dongchang Chemical Industrial Co., Ltd., Nantong 226407, P. R. China;
3. China National Offshore Oil Corp., Tianjin Chemical Research and Design Institute, Tianjin 300131, P. R. China

收稿日期:2016-01-20 修回日期:2016-03-18 出版日期:2016-08-01 发布日期:2016-05-30
通讯作者: QU Hongmei E-mail:ququhongmei@126.com
基金资助:
Supported by the National Natural Science Foundation of China(No.21102099).

Zirconium-mediated Selective Synthesis of Quinoline Derivatives

MEN Yican¹, ZHANG Jiqian², ZHOU Lishan³, LI Junqiu¹, LIU Jun¹, LI Juan¹, QU Hongmei¹

1. Key Laboratory of Systems Bioengineering, Ministry of Education, Tianjin Key Laboratory of Biological and Pharmaceutical Engineering, Department of Pharmaceutical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China;
2. Nantong Dongchang Chemical Industrial Co., Ltd., Nantong 226407, P. R. China;
3. China National Offshore Oil Corp., Tianjin Chemical Research and Design Institute, Tianjin 300131, P. R. China

Received:2016-01-20 Revised:2016-03-18 Online:2016-08-01 Published:2016-05-30
Contact: QU Hongmei E-mail:ququhongmei@126.com
Supported by:
Supported by the National Natural Science Foundation of China(No.21102099).

摘要/Abstract

摘要：

A series of quinoline derivatives was obtained in high yields by an efficient one-pot reaction of substituted o-diiodobenzenes with azazirconacyclopentadienes, which were conveniently prepared from one internal alkyne and one nitrile mediated by zirconocene. This proposed synthetic method provides a feasible way to the synthesis of large N-heterocyclic π-conjugated molecules.

关键词: Azazirconacyclopentadiene, One-pot reaction, Quinoline derivative, Zirconocene

Abstract:

Key words: Azazirconacyclopentadiene, One-pot reaction, Quinoline derivative, Zirconocene

MEN Yican, ZHANG Jiqian, ZHOU Lishan, LI Junqiu, LIU Jun, LI Juan, QU Hongmei. Zirconium-mediated Selective Synthesis of Quinoline Derivatives[J]. 高等学校化学研究, 2016, 32(4): 621-624.

MEN Yican, ZHANG Jiqian, ZHOU Lishan, LI Junqiu, LIU Jun, LI Juan, QU Hongmei. Zirconium-mediated Selective Synthesis of Quinoline Derivatives[J]. Chemical Research in Chinese Universities, 2016, 32(4): 621-624.

参考文献

[1] Kwiek J. K., Haystead T. A., Rudolph J., Biochemistry, 2004, 43(15), 4538
[2] EI-Zohry M. F., Ahmed A. N., Omar F. A., Abd-Alla M. A., J. Chem. Technol. Biotechnol., 1992, 53(4), 329
[3] Yuan J., Su X., Zhang X., Cong L., Guo C., Chem. Res. Chinese Universities, 2011, 27(6), 955
[4] Patel N. C., Mehta A. G., Ultra Scientist of Physical Sciences, 2004, 16(1), 147
[5] Hu H., Jiang M. Y., Xie L. J., Hu G., Zhang C. R., Zhang L. X., Zhou S. G., Zhang M. H., Chem. Res. Chinese Universities, 2015, 31(5), 746
[6] Luo Z. G., Zeng C. C., Wang F., He H. Q., Wang C. X., Du H. G., Hu L. M., Chem. Res. Chinese Universities, 2009, 25(6), 841
[7] Rafiee E., Nejad F. K., Joshaghani M., Chin. Chem. Lett., 2011, 22(3), 288
[8] Zhu H., Yang R. F., Yun L. H., Li J., Chin. Chem. Lett., 2010, 21(1), 35
[9] Cohn B. E., Gustavson R. G., J. Am. Chem. Soc., 1928, 50, 2709
[10] Guo Q. X., Rao S. S., Ren S. Y., Xu J., Chem. Res., 2013, 24(6), 569
[11] Wang Y. X., Liao Q., Zhao P., Xi C. J., Adv. Synth. Catal., 2011, 353(14), 2659
[12] Kong L. H., Yu S. J., Zhou X. K., Li X. W., Org. Lett., 2016, 18(3), 588
[13] Takahashi T., Xi Z. F., Yamazaki A., Liu Y. H., Nakajima K., Kotora M., J. Am. Chem. Soc., 1998, 120(8), 1672
[14] Xi Z. F., Zhang W. X., Synlett., 2008, (17), 2557
[15] Xi Z. F., Li Z. P., Topics in Organometallic Chemisty, 2005, 8, 27
[16] Chen C., Xi C. J., Jiang Y. F., Hong X. Y., J. Am. Chem. Soc., 2005, 127(22), 8024
[17] Takahashi T., Li Y. Z., Stepnicka P., Kitamura M., Liu Y. J., Nakajima K., Kotora M., J. Am. Chem. Soc., 2002, 124(4), 576
[18] Gu D., Harpp D. N., Tetrahedron Lett., 1993, 34(1), 67
[19] Takahashi T., Xi C. J., Xi Z. F., Kageyama M., Fischer R., Nakajima K., Negishi E., J. Org. Chem., 1998, 63(20), 6802
[20] Li S., Qu H. M., Zhou L. S., Kanno K., Guo Q. X., Shen B. J., Takahashi T., Org. Lett., 2009, 11(15), 3318
[21] Seri T., Qu H. M., Zhou L. S., Kanno K., Takahashi T., Chem. Asian J., 2008, 3(2), 388

Zirconium-mediated Selective Synthesis of Quinoline Derivatives

Zirconium-mediated Selective Synthesis of Quinoline Derivatives

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