European Journal of Chemistry 2011, 2(2), 173-177 | doi: https://doi.org/10.5155/eurjchem.2.2.173-177.283 | Get rights and content






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

Research on the reaction of furil with ammonium acetate


Shuaijun Wang (1) , Qiang Gu (2) , Xiaodong Chen (3) , Tianqi Zhao (4) , Yumin Zhang (5,*)

(1) College of Chemistry, Jilin University, Changchun 130012, China
(2) College of Chemistry, Jilin University, Changchun 130012, China
(3) Experimental Center of Testing Science, Jilin University, Changchun 130023, China
(4) College of Chemistry, Jilin University, Changchun 130012, China
(5) College of Chemistry, Jilin University, Changchun 130012, China
(*) Corresponding Author

Received: 15 Sep 2010 | Revised: 29 Nov 2010 | Accepted: 08 Dec 2010 | Published: 30 Jun 2011 | Issue Date: June 2011

Abstract


The direct reaction of furil with ammonium acetate in refluxing glacial acetic acid under the absence of appropriate aldehydes was systematically studied. The principal product with furan rings and imidazole ring 2,4,5-tri(furan-2-yl)-1H-imidazole (I) was obtained in moderate yield, and two new byproducts containing furan rings were successfully purified by C18 reversed phase column. All compounds were characterized by elemental analysis, MS, IR, 1H and 13C NMR spectroscopy. The structure of I was further confirmed by the 13C-1H COSY spectroscopy. The putative reaction mechanism via stable 1,2-di(furan-2-yl)ethane-1,2-diimine, furan-2-yl-(2,4,5-tri-furan-2-yl-2H-imidazol-2-yl)-methanone and intermediate 5 traced by GC-MS was proposed.2_2_173_177_800

Keywords


1,2-di(furan-2-yl)ethane-1,2-diimine; Furil; Ammonium acetate; Heterocycles; Mechanism; Furan derivatives

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.2.173-177.283

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 1179 times | PDF Article downloaded 373 times


Citations

/


[1]. Eduardo Varanda, Maíra Do Prado, Renata A. Simão, Katia Regina Hostílio Cervantes Dias
Effect of in-office bleaching agents on the surface roughness and morphology of different dental composites: An AFM study
Microscopy Research and Technique  76(5), 481, 2013
DOI: 10.1002/jemt.22190
/


[2]. Rajendran Suresh, Shanmugam Muthusubramanian, Muthusamy Boominathan, Govindaswamy Manickam
Acid controlled generation of indanes and oxazolines from β-hydroxyarylethanamide
Tetrahedron Letters  54(19), 2315, 2013
DOI: 10.1016/j.tetlet.2013.02.033
/


[3]. Mahmoud H. El-Maghrabey, Naoya Kishikawa, Kaname Ohyama, Naotaka Kuroda
Analytical method for lipoperoxidation relevant reactive aldehydes in human sera by high-performance liquid chromatography–fluorescence detection
Analytical Biochemistry  464, 36, 2014
DOI: 10.1016/j.ab.2014.07.002
/


[4]. Lu Yao Wang, Dong Meng, Lu Li, Xin Cai
An Efficient Synthesis of Furil
Advanced Materials Research  554-556, 764, 2012
DOI: 10.4028/www.scientific.net/AMR.554-556.764
/


References

[1]. Balalaie, S.; Arabanian, A. Green Chem. 2000, 2, 274-276.
doi:10.1039/b006201o

[2]. Zhang, C. Z.; Moran, E. J.; Woiwode, T. F. Tetrahedron Lett. 1996, 37(6), 751-754.
doi:10.1016/0040-4039(95)02310-0

[3]. Huang, W.; Pei, J.; Chen, B.-Z.; Pei, W. W.; Ye, X. L. Tetrahedron 1996, 52(30), 10131-10136.
doi:10.1016/0040-4020(96)00552-2

[4]. Fang, Z. J.; Wang, S. M.; Zhao, L.; Xu, Z. X.; Ren, J.; Wang, X. B.; Yang, Q. F. Materials Lett. 2007, 61, 4803-4806.
doi:10.1016/j.matlet.2007.03.038

[5]. Parveen, A.; Ahmed M. R. S.; Shaikh K. A.; Deshmukh S. P.; Pawar R. P. Arkivoc 2007, 16, 12-18.

[6]. Santos, J.; Mintz, E. A.; Zehnder, O.; Bosshard, C.; Bu, X. R.; Günter, P. Tetrahedron Lett. 2001. 42(5), 805-808.
doi:10.1016/S0040-4039(00)02143-2

[7]. Dora, B. K.; Dash, B.; Panda, C. S. J. Indian Chem. Soc. 1979, LVI, 620-624.

[8]. Colin L. R.; Gareth W.; Cave, V. J. J. Chem. Edu. 2005, 82, 468-469.
doi:10.1021/ed082p468

[9]. Wang, J.; Mason, R.; VanDerveer, D.; Feng, K.; Bu, X. R. J. Org. Chem. 2003, 68, 5415-5418.
doi:10.1021/jo0342020
PMid:12816512

[10]. Zhao, L.; Li, Sh. B.; Wen, G. A.; Peng, B.; Huang, W. Mater. Chem. Phy. 2006, 100, 460-463.
doi:10.1016/j.matchemphys.2006.01.025

[11]. Crouch, R. D.; Howard, J. L.; Zile, J. L.; Barker, K. H. J. Chem. Edu. 2006, 83(11), 1658-1660.
doi:10.1021/ed083p1658

[12]. Radziszewski, B. Ber. Deut. Chem. Ges. (Ber.) 1882, 15(2), 1493-1496.
doi:10.1002/cber.18820150207

[13]. Davidson, D.; Weiss, M.; Jelling, M. J. Org. Chem. 1937, 2, 319-327.
doi:10.1021/jo01227a004

[14]. Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles: Structures, Reaction, Synthesis and Application, Wiley-Vch Gmbh Co. KgaA, 46-47, 2003.

[15]. Wu, Y. L.; Ma, Sh. M.; Dai, L. X. Advances in Modern Organic Synthetic Chemistry, 1st edition, Chemical Industry Press, 2005.

[16]. Li, Y. Zh.; Zhang, F.; Jia, X. F.; Gao, D. W.; Zhang, Y. M.; Zhao, T. Q.; Chen, X. D. Heterocycl. Commun. 2006, 12, 361-364.
doi:10.1515/HC.2006.12.5.361

[17]. Gao, D. W.; Yu, H. F.; Jia, J. L.; Hua, S. Y.; Chen, X. D. Acta Sci. Naturalium Universitatis Jilinensis 1998, 1, 107-109.

[18]. Davidson, D.; Weiss, M.; Jelling, M. J. Org. Chem. 1937, 2, 328-334.
doi:10.1021/jo01227a005

[19]. Wang, S. J.; Gu, Q; Su, Q; Chen, X. D.; Zhang, Y. M. Acta Cryst. 2009, E65, o3194-o3194.

Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Wang, S.; Gu, Q.; Chen, X.; Zhao, T.; Zhang, Y. Eur. J. Chem. 2011, 2(2), 173-177. doi:10.5155/eurjchem.2.2.173-177.283
Wang, S.; Gu, Q.; Chen, X.; Zhao, T.; Zhang, Y. Research on the reaction of furil with ammonium acetate. Eur. J. Chem. 2011, 2(2), 173-177. doi:10.5155/eurjchem.2.2.173-177.283
Wang, S., Gu, Q., Chen, X., Zhao, T., & Zhang, Y. (2011). Research on the reaction of furil with ammonium acetate. European Journal of Chemistry, 2(2), 173-177. doi:10.5155/eurjchem.2.2.173-177.283
Wang, Shuaijun, Qiang Gu, Xiaodong Chen, Tianqi Zhao, & Yumin Zhang. "Research on the reaction of furil with ammonium acetate." European Journal of Chemistry [Online], 2.2 (2011): 173-177. Web. 24 Jan. 2020
Wang, Shuaijun, Gu, Qiang, Chen, Xiaodong, Zhao, Tianqi, AND Zhang, Yumin. "Research on the reaction of furil with ammonium acetate" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.2.173-177.283

| | | | |

| | | | | |

Save to Zotero Save to Mendeley

European Journal of Chemistry 2011, 2(2), 173-177 | doi: https://doi.org/10.5155/eurjchem.2.2.173-177.283 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  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 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort