One-pot Three-component Reaction for Efficient and Facile Synthesis of γ-Nitrocarbonyl Compounds Under Solvent-free Conditions

doi:10.1007/s40242-015-4410-1

高等学校化学研究 ›› 2015, Vol. 31 ›› Issue (2): 208-211.doi: 10.1007/s40242-015-4410-1

One-pot Three-component Reaction for Efficient and Facile Synthesis of γ-Nitrocarbonyl Compounds Under Solvent-free Conditions

LÜ Chengwei, LIU Yanhang, ZHOU Xiaoxia, WANG Jiajing

Shcool of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, P. R. China

收稿日期:2014-10-29 修回日期:2014-11-26 出版日期:2015-04-01 发布日期:2015-01-04
通讯作者: LÜ Chengwei E-mail:chengweilv@126.com
基金资助:
Supported by the National Natural Science Foundation of China(No.21403100) and the Doctoral Scientific Research Foundation of Liaoning Province, China(No.20141100).

One-pot Three-component Reaction for Efficient and Facile Synthesis of γ-Nitrocarbonyl Compounds Under Solvent-free Conditions

LÜ Chengwei, LIU Yanhang, ZHOU Xiaoxia, WANG Jiajing

Shcool of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, P. R. China

Received:2014-10-29 Revised:2014-11-26 Online:2015-04-01 Published:2015-01-04
Contact: LÜ Chengwei E-mail:chengweilv@126.com
Supported by:
Supported by the National Natural Science Foundation of China(No.21403100) and the Doctoral Scientific Research Foundation of Liaoning Province, China(No.20141100).

摘要/Abstract

摘要：

A simple and efficient protocol was established to synthesize γ-nitrocarbonyl compounds via three-component one-pot tandem condensation reaction of aldehydes, Meldrum's acid and nitroalkanes under solvent- free conditions. The present method shows fascinating features such as using readily available starting materials, promoting the yields by inexpensive and mild organic base triethylamine, omiting the synthesis of Michael acceptor and avoiding the use of organic solvent. This strategy provides an easy alternative synthetic approach to the useful intermediate, γ-nitrocarbonyl compounds, with moderate to good yields.

关键词: γ-Nitrocarbonyl compound, Multicomponent reaction, One-pot reaction, Solvent free

Abstract:

Key words: γ-Nitrocarbonyl compound, Multicomponent reaction, One-pot reaction, Solvent free

LÜ Chengwei, LIU Yanhang, ZHOU Xiaoxia, WANG Jiajing. One-pot Three-component Reaction for Efficient and Facile Synthesis of γ-Nitrocarbonyl Compounds Under Solvent-free Conditions[J]. 高等学校化学研究, 2015, 31(2): 208-211.

参考文献

[1] Mitchell C. E. T., Brenner S. E., Ley S. V., Chem. Commun., 2005, 41(42), 5346
[2] Mei K., Jin M., Zhang S., Li P., Liu W., Chen X., Xue F., Duan W., Wang W., Org. Lett., 2009, 11(13), 2864
[3] Roca-Lopez D., Sadaba D., Delso I., Herrera R. P., Tejero T., Merino P., Tetrahedron: Asymmetry, 2010, 21(21/22), 2561
[4] Ballini R., Bosica G., Fiorini D., Palmieri A., Petrini M., Chem. Rev., 2005, 105(3), 933
[5] Krishna P. R., Sreeshailam A., Srinivas R., Tetrahedron, 2009, 65(47), 9657
[6] Lia J. H., Li Z. G., Chen Q. G., J. Chem. Res., 2004, 758
[7] Bassas O., Huuskonen J., Rissanen K., KosKinen A. M. P., Eur. J. Org. Chem., 2009, 1340
[8] Didiera D., Sergeyev S., Arkivoc, 2009, (xiv), 124
[9] Kataja A. O., Koskinen A. M. P., Arkivoc, 2010, (ii), 205
[10] Lou H. W., Zhang T., Li K., Zhang M., Li J. H., Chin. J. Org. Chem., 2011, 31(8), 1258
[11] Leyva-Pérez A., García-García P., Corma A., Angew. Chem. Int. Ed., 2014, 53(33), 8687
[12] Schreiber S. L., Science, 2000, 287(5460), 1964
[13] Wen L. R., Li Z. R., Li M., Cao H., Green Chem., 2012, 14(3), 707
[14] Jiang B., Rajale T., Wever W., Tu S. J., Li G. G., Chem. Asian J., 2010, 5(11), 2318
[15] Lin X. F., Mao Z. J., Dai X. X., Lu P., Wang Y. G., Chem. Commun., 2011, 47(23), 6620
[16] Hong D., Zhu Y. X., Li Y., Lin X. F., Lu P., Wang Y. G., Org. Lett., 2011, 13(17), 4668
[17] Ghahremanzadeh R., Rashid Z., Zarnani A. H., Naeimi H., Ultrason. Sonochem., 2014, 21(4), 1451
[18] Toure B. B., Hall D. G., Chem. Rev., 2009, 109(9), 4439
[19] Candeias N. R., Montalbano F., Cal P. M., Gois P. M. P., Chem. Rev., 2010, 110(10), 6169
[20] Ramachary D. B., Jain S., Org. Biomol. Chem., 2011, 9(5), 1277
[21] Bonfield E. R., Li C. J., Adv. Synth. Catal., 2008, 350(3), 370
[22] Elders N., vander Born D., Hendrickx L. J. D., Timmer B. J. J., Krause A., Janssen E., de Kanter F. J. J., Ruijter E., Orru R. V. A., Angew. Chem. Int. Ed., 2009, 48(32), 5856
[23] Brahmachari G., Das S., Tetrahedron Lett., 2012, 53(12), 1479
[24] Deng H., Li Z., Ke F., Zhou X., Chem. Eur. J., 2012, 18(16), 4840
[25] Sunderhaus J. D., Dockendorff C., Martin S. F., Tetrahedron, 2009, 65(33), 6454
[26] Tu X. C., Feng H., Tu M. S., Jiang B., Wang S. L., Tu S. J., Tetrahedron Lett., 2012, 53(25), 3169
[27] Yu J., Shi F., Gong L. Z., Acc. Chem. Res., 2011, 44(11), 1156
[28] Dömling A., Wang W., Wang K., Chem. Rev., 2012, 112(6), 3083
[29] Hajipour A. R., Ghayeb Y., Sheikhan N., Tetrahedron Lett., 2009, 50(40), 5649
[30] Jiang B., Xue L. Y., Wang X. H., Tu M. S., Liu Y. P., Tu S. J., Tetrahedron Lett., 2012, 53(10), 1261
[31] Aditya K., Béla T., Green Chem., 2010, 12(5), 875
[32] Ma N., Jiang B., Zhang G., Tu S. J., Wever W., Li G. G., Green Chem., 2010, 12(8), 1357
[33] Cheng C., Jiang B., Tu S. J., Li G. G., Green Chem., 2011, 13(8), 2107
[34] Martins M. A. P., Frizzo C. P., Moreira D. N., Buriol L., Machado P., Chem. Rev., 2009, 109(9), 4140
[35] Kumar R., Raghuvanshi K., Verma R. K., Singh M. S., Tetrahedron Lett., 2010, 51(45), 5933
[36] Kidwai M., Jahan A., Chauhan R., Mishra N. K., Tetrahedron Lett., 2012, 53(14), 1728
[37] Wen L. R., Li Z. R., Li M., Cao H., Green Chem., 2012, 14(3), 707
[38] Zong C. L., Zeng R. S., Zou J. P., Chem. Res. Chinese Universities, 2014, 30(4), 632
[39] Poe S. L., Kobašlija M., McQuade D. T., J. Am. Chem. Soc., 2006, 128(49), 15586
[40] Poe S. L., Kobašlija M., McQuade D. T., J. Am. Chem. Soc., 2007, 129(29), 9216
[41] Li Y. L., Zhao B., Du B. X., Jiang Q. S., Wang X. S., Cao C. S., Tetrahedron Lett., 2013, 54(3), 227
[42] Gusarova N. K., Volkov P. A., Ivanova N. I., Sukhov B. G., Larina L. I., Kazheva O. N., Alexandrov G. G., D'yachenko O. A., Trofimov B. A., Tetrahedron Lett., 2013, 54(49), 6772
[43] Yavari I., Beheshti S., Hossaini Z., Souri S., Synth. Commun., 2011, 41(6), 907
[44] Wassima G., Raouf B., Abdelmadjid D., Chin. J. Chem., 2012, 30(3), 733

One-pot Three-component Reaction for Efficient and Facile Synthesis of γ-Nitrocarbonyl Compounds Under Solvent-free Conditions

One-pot Three-component Reaction for Efficient and Facile Synthesis of γ-Nitrocarbonyl Compounds Under Solvent-free Conditions

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 8

编辑推荐

Metrics

本文评价

[1]	JIANG Ling, YE Wenting, SU Weike, YU Chuanming. Application of Enzymatic Promiscuity in Pharmaceutical Synthesis: Papain-catalyzed One-pot Synthesis of 1,4-Dihydropyridine Calcium Channel Antagonists and Derivatives[J]. 高等学校化学研究, 2019, 35(1): 21-25.
[2]	WANG Yue, HOU Dalong, LÜ Haoze, ZHANG Baozhen, WANG Ensi. Efficient Synthesis of Beraprost Sodium[J]. 高等学校化学研究, 2016, 32(4): 581-585.
[3]	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.
[4]	WANG Ying-lei, LUO Jun, ZHI Hui-zhen. Preparation of 3,4-Dihydropyrimidones via Biginelli Reaction in Efficient and Recyclable PEG₁₀₀₀-DAIL/Toluene Catalyst-mediumCombined Thermoregulated Biphasic System[J]. 高等学校化学研究, 2013, 29(5): 879-883.
[5]	LIU Zhen-ming, WU Lei, SUN Jing, YAN Chao-guo. Efficient One-pot Synthesis of Pyrrolo[2,1-a]isoquinoline and Pyrrolo[1,2-a]quinoline Derivatives[J]. 高等学校化学研究, 2012, 28(6): 990-993.
[6]	AN Lin, LIU Dong-mei, WANG Jin-xiang and YAN Chao-guo*. Microwave Assisted Synthesis of 3,3',3″,3'″-o-, p-Phenylenedi-methylidinetetrakis-(4-hydroxy-2H-1-benzopyran-2-one)[J]. 高等学校化学研究, 2010, 26(6): 933-936.
[7]	CHEN Jiao, MA Zhen and YAN Chao-guo*. Three-component Reaction of Aromatic Aldehyde, Malononitrile and Aliphatic Amine Leading to Different Pyridine Derivatives[J]. 高等学校化学研究, 2010, 26(6): 937-941.
[8]	JIN Hua, QI Yan-fei, QIN Chao, WANG Xin-long, WANG En-bo, XU Lin. [Ce(H₂ O)₇ Al(OH)₆ Mo₆O₁₈]·4H₂ O: A New One-dimensional Zigzag Chainlike Structure of Anderson Cluster Linked by Cerium Ions[J]. 高等学校化学研究, 2005, 21(6): 637-640.