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

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (2): 208-211.doi: 10.1007/s40242-015-4410-1

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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).

Abstract

Abstract:

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.

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]. Chemical Research in Chinese Universities, 2015, 31(2): 208-211.

References

[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

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