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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.
Keywords
1,2-di(furan-2-yl)ethane-1,2-diimine; Furil; Ammonium acetate; Heterocycles; Mechanism; Furan derivatives
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DOI: 10.5155/eurjchem.2.2.173-177.283
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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.
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. 28 May. 2022
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)
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.2.2.173-177.283
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