One-Pot Three-Component Synthesis of New β-Indole Derivatives in Gluconic Acid Aqueous Solution

doi:10.6023/cjoc201406010

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2487-2492.DOI: 10.6023/cjoc201406010 Previous Articles Next Articles

ARTICLE

葡萄糖酸溶液中三组分一锅法合成新型β-吲哚衍生物

严楠^a,b, 夏剑辉^b, 熊云奎^b, 熊斌^b, 林春花^a,b, 廖维林^a,b

a. 国家单糖化学合成工程技术研究中心南昌 330027;
b. 江西师范大学化工研发中心南昌 330027

收稿日期:2014-06-18 修回日期:2014-07-09 发布日期:2014-08-29
通讯作者: 林春花 E-mail:ldyannan104@tom.com
基金资助:
国家科技支撑计划(No.2009BAI75B02)、江西省研究生创新基金(No.YC2014)、江西师范大学优秀博士论文培育计划资助项目.

One-Pot Three-Component Synthesis of New β-Indole Derivatives in Gluconic Acid Aqueous Solution

Yan Nan^a,b, Xia Jianhui^b, Xiong Yunkui^b, Xiong Bin^b, Lin Chunhua^a,b, Liao Weilin^a,b

a. National Monosaccharide Chemical Synthesis Engineering Research Center, Nanchang 330027;
b. Chemical Research and Development Center, Jiangxi Normal University, Nanchang 330027

Received:2014-06-18 Revised:2014-07-09 Published:2014-08-29
Supported by:
Project supported by the National Science and Technology Support Program of China (No. 2009BAI75B02), the Innovation Fund Designated for Graduate Students of Jiangxi Province (No. YC2014), and the Outstanding Doctoral Dissertation Cultivation Program of Jiangxi Normal University.

One-pot three-component reactions of aldehydes with indole and 2,2-pentamethylene-1,3-dioxane-4,6-dione afforded thirteen kinds of 5-[(indol-3-yl)-methyl]-2,2-pentamethylene-1,3-dioxane-4,6-dione derivatives (β-indole derivatives) in the presence of gluconic acid aqueous solution in 66.4%～98.5% yields. The advantages of this protocol were mild reaction conditions, wide substrate scope, high yields and benign to environment, which afforded an effective method to synthesize β-indole derivatives.

Key words: 2,2-pentamethylene-1,3-dioxane-4,6-dione, gluconic acid aqueous solution, three-component reactions, β-indole derivatives

Cite this article

Yan Nan, Xia Jianhui, Xiong Yunkui, Xiong Bin, Lin Chunhua, Liao Weilin. One-Pot Three-Component Synthesis of New β-Indole Derivatives in Gluconic Acid Aqueous Solution[J]. Chin. J. Org. Chem., 2014, 34(12): 2487-2492.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Yang, D.-L.; Li, J.-R.; Sun, K.-N.; Lu, H.-Y.; Liu, M.-X.; Shi, D.-X. Chin. J. Org. Chem. 2013, 33, 2341 (in Chinese). (杨德利, 李加荣, 孙克宁, 路红燕, 刘明星, 史大昕, 有机化学, 2013, 33, 2341.)
[2] Tong, G.-J.; Fan, W.; Jiang, B. Chin. J. Org Chem. 2013, 33, 2578 (in Chinese). (佟光进, 范威, 姜波, 有机化学, 2013, 33, 2578.)
[3] Dömling, A. Chem. Rev. 2006, 106, 17.
[4] Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083.
[5] Francesco, E.; Salvatore, G.; Ornelio, R.; Silvia, T.; Caroline, P.; Massimo, C. Tetrahedron Lett. 2011, 52, 568.
[6] Csaba, N.; Laurent, J.; Janos, S.-T. Tetrahedron Lett. 2000, 56, 5479.
[7] Stéphane, G.; Bérangère, L.; Antonella, F.; Paolode, M.; Janos, S. Tetrahedron 2010, 66, 3065.
[8] Armstrong, E.-L.; Grover, H.-K.; Kerr, M.-A. J. Org. Chem. 2013, 78, 10534.
[9] Oikawa, Y., Hirasawa, H., Yonemitsu, O. Tetrahedron Lett. 1978, 19(20), 1759.
[10] Wang, H.-Y.; Li, L.-L.; Li, W.; Huang, Z.-B.; Shi, D.-Q. Chin. J. Org. Chem. 2013, 33, 1616 (in Chinese). (汪辉员, 李丽丽, 林伟, 黄志斌, 史达清, 有机化学, 2013, 33, 1616.)
[11] Renzetti, A.; Dardennes, E.; Fontana, A.; Maria, P.-D.; Sapi, J.; Gerard, S. J. Org. Chem. 2008, 73, 6824.
[12] Chandrasekhar, S.; Patro, V.; Reddy, G.-P.; Grée, R. Tetrahedron Lett. 2012, 53, 6223.
[13] Qu, Y.-Y.; Ke, F.; Zhou, L.; Li, Z.-K.; Xiang, H.-F.; Wu, D.; Zhou, X.-G. Chem. Commun. 2011, 47, 3912.
[14] Liu, B.-M.; Zhang, D.-L.; Guo, X.-M.; Li, H.-Z. Chin. J. Synth. Chem. 2004, 12, 505 (in Chinese). (刘卉闵, 张冬暖, 果秀敏, 李惠章, 合成化学, 2004, 12, 505.)
[15] Wang, C.; Zhang, Y.-Q.; Li, G.-S.; Li, J.-C.; Li, X.-L. Chin. J. Org. Chem. 2003, 23, 1416 (in Chinese). (王春, 张英群, 李贵深, 李敬慈, 李晓陆, 有机化学, 2003, 23, 1416.)
[16] Sheng, W.-L.; Du, Y.-Y.; Tian, F.-L.; Han, L.-M.; Zhu, N. Chemistry 2012, 75, 1026 (in Chinese). (盛万里, 杜玉英, 田福利, 韩利民, 竺宁, 化学通报, 2012, 75, 1026.)
[17] Zhou, B.-H.; Yang, J.; Li, M.-H.; Gu, Y.-L. Green Chem. 2011, 13, 2204.
[18] Guo, R.-Y.; Wang, P.; Wang, G.-D.; Mo, L.-P.; Zhang, Z.-H. Tetrahedron 2013, 69, 2056.
[19] Yan, N.; Xiong, B.; Liao, W.-L.; Xu, Z.-H. Chin. J. Org. Chem. 2010, 30, 1391 (in Chinese). (严楠, 熊斌, 廖维林, 许招会, 有机化学, 2010, 30, 1391.)

葡萄糖酸溶液中三组分一锅法合成新型β-吲哚衍生物

One-Pot Three-Component Synthesis of New β-Indole Derivatives in Gluconic Acid Aqueous Solution

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	Lin Chunhua, Yuan Jianjun, Liu Deyong, Zhang Houfu, Xu Zhaohui. Efficient Synthesis of 5,5-(Phenylmethylene)bis(2,2-dimethyl-1,3-dioxane-4,6-dione) Derivatives in Biobased Gluconic Acid Aqueous Solution [J]. Chin. J. Org. Chem., 2017, 37(6): 1560-1564.
[2]	Lü Chengwei, Liu Yanhang, Zhou Xiaoxia. Efficient and Green Synthesis of 5-[(Indole-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione Derivatives in the Melt [J]. Chin. J. Org. Chem., 2016, 36(6): 1407-1411.