European Journal of Chemistry 2011, 2(3), 308-310 | doi: https://doi.org/10.5155/eurjchem.2.3.308-310.126 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis and optimization of methyl 5-acetyl-1,4-dihydro-2,6-dimethyl-4-(substituent benzylidene)pyridine-3-carboxylate


Rui Dong Liu (1) , Jian Zhang (2,*)

(1) College of Chemistry and Materials, South-Central University for Nationalities, Wuhan, 430074, China
(2) College of Chemistry and Materials, South-Central University for Nationalities, Wuhan, 430074, China
(*) Corresponding Author

Received: 27 May 2010 | Revised: 24 Feb 2011 | Accepted: 28 Oct 2010 | Published: 30 Sep 2011 | Issue Date: September 2011

Abstract


Two 1,4-dihydro-Hantzsch pyridine derivatives were synthesized by three steps. In the condensation step, the reaction time can be shortened to 1.5 h through using H2SO4-acetic anhydride system as a catalyst rather than the acetic acid-piperidine systemin the cyclization step, the reaction time was shortened from 20 h in ethanol to 15 h in polar aprotic solvent, and the yield of two products also was increased from 43.3% and 39.7% in traditional solvent to 93.2% and 90.1% in polar aprotic solvent.

2_3_308_310_800


Keywords


Unsymmetrical; 1,4-dihydro-Hantzsch pyridine; Condensation; Catalyst; Cyclization; Polar aprotic solvent

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.3.308-310.126

Links for Article


| | | | | | |

| | | | | | |

| |

Related Articles




Article Metrics

This Abstract was viewed 612 times | PDF Article downloaded 341 times

Funding information


South-Central University for Nationalities

Citations

/


[1]. Ling Jiang, Hongwei Yu
Enzymatic promiscuity: Escherichia coli BioH esterase-catalysed Aldol reaction and Knoevenagel reaction
Chemical Research in Chinese Universities  30(2), 289, 2014
DOI: 10.1007/s40242-014-3401-y
/


[2]. Hua Li, Deliang Zhang, Mengna Gao, Lumei Huang, Longguang Tang, Zijing Li, Xiaoyuan Chen, Xianzhong Zhang
Highly specific C–C bond cleavage induced FRET fluorescence for in vivo biological nitric oxide imaging
Chemical Science  8(3), 2199, 2017
DOI: 10.1039/C6SC04071C
/


References

[1]. Satish, K.; Poonam, S.; Kamal, K. Tetrahedron 2008, 64, 536-538.
http://dx.doi.org/10.1016/j.tet.2007.11.008

[2]. Javid, S. M.; Mojarrad, V. D.; Carlos, V.; Edward, E. K. Bioorg. Med. Chem. Lett. 2005, 13, 4085-4091.
http://dx.doi.org/10.1016/j.bmc.2005.03.047

[3]. Muchchinatala, M.; Vidavalur, S.; Yerra, K. R. J Mol. Catal. A: Chem. 2006, 260, 179-180.
http://dx.doi.org/10.1016/j.molcata.2006.07.024

[4]. Churchil, A. A.; Kannan, S. Appl. Catal. A: General 2008, 338, 121-125.
http://dx.doi.org/10.1016/j.apcata.2007.12.028

[5]. Shi, D. Q.; Mou, J.; Tu, S. J. Chinese J. Org. Chem. 2004, 24, 1042-1044.

[6]. Saikat, D. S.; Parasa, H.; Dllip, K. Catal. Commun. 2008, 9, 709-714.
http://dx.doi.org/10.1016/j.catcom.2007.08.008

[7]. Zhang, B. L.; He, W.; Shi, X.; Huan, M. L.; Huang, Q. J. Bioorg. Med. Chem. Lett. 2010, 20, 805-806.
http://dx.doi.org/10.1016/j.bmcl.2009.12.104

[8]. Deng, L.; Xu, M. X. Chem. Res. Appl. 2002, 14, 233-234.

[9]. Lin, C. Z.; Ko, S. K. Tetrahedron Lett. 2005, 46, 5771-5774.
http://dx.doi.org/10.1016/j.tetlet.2005.05.148

[10]. Zhang, X. Y.; Li, Y. Z.; Fan, X. S.; Qu, G. R. Chinese Chem. Lett. 2006, 17, 150-152.

[11]. Amini, M. A.; Golabchifar. A.; Dehpour A. R. Drug Res. 2002, 52, 21-26.

[12]. Dondoni, A.; Massi, A.; Minghini, E.; Bertolasi, V. Tetrahedron 2004, 60, 2311-2326.
http://dx.doi.org/10.1016/j.tet.2004.01.011

[13]. Liu, H. C.; Feng, Y. Q. Chem. Ind. Eng. 2006, 23, 88-91.

How to cite


Liu, R.; Zhang, J. Eur. J. Chem. 2011, 2(3), 308-310. doi:10.5155/eurjchem.2.3.308-310.126
Liu, R.; Zhang, J. Synthesis and optimization of methyl 5-acetyl-1,4-dihydro-2,6-dimethyl-4-(substituent benzylidene)pyridine-3-carboxylate. Eur. J. Chem. 2011, 2(3), 308-310. doi:10.5155/eurjchem.2.3.308-310.126
Liu, R., & Zhang, J. (2011). Synthesis and optimization of methyl 5-acetyl-1,4-dihydro-2,6-dimethyl-4-(substituent benzylidene)pyridine-3-carboxylate. European Journal of Chemistry, 2(3), 308-310. doi:10.5155/eurjchem.2.3.308-310.126
Liu, Rui, & Jian Zhang. "Synthesis and optimization of methyl 5-acetyl-1,4-dihydro-2,6-dimethyl-4-(substituent benzylidene)pyridine-3-carboxylate." European Journal of Chemistry [Online], 2.3 (2011): 308-310. Web. 28 Nov. 2020
Liu, Rui, AND Zhang, Jian. "Synthesis and optimization of methyl 5-acetyl-1,4-dihydro-2,6-dimethyl-4-(substituent benzylidene)pyridine-3-carboxylate" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


DOI Link: https://doi.org/10.5155/eurjchem.2.3.308-310.126

| | | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2011, 2(3), 308-310 | doi: https://doi.org/10.5155/eurjchem.2.3.308-310.126 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.