Citation: Razieh Doostmohammadi, Malek Taher Maghsoodlou, Nourallah Hazeri, Sayyed Mostafa Habibi-Khorassani. An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate[J]. Chinese Chemical Letters, ;2013, 24(10): 901-903. shu

An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate

1.
Department of Chemistry, Faculty of Science, The University of Sistan and Baluchestan, PO Box 98135-674, Zahedan, Iran

Corresponding author: Malek Taher Maghsoodlou,
Received Date: 25 March 2013
Available Online: 24 May 2013
Fund Project:

A facile one-pot synthesis of 3,4,5-substituted furan-2(5H)-one derivatives from a three-component reaction of aniline derivatives, dialkylacetylenedicarboxylates and aromatic aldehydes under mild conditions using tetra-n-butylammonium bisulfate as a catalyst has been developed.
- 3,4,5-Substituted furan-2(5H)-one,
- Aniline derivative,
- Dialkyl acetylenedicarboxylate,
- Aromatic aldehyde,
- Tetra-n-butylammonium bisulfate
1. [1]
  [1] F.A.Dean, Naturally Occurring Oxygen Ring Compounds, Butterworth, London, 1963.
2. [2]
  [2] K. Nakanishi, T. Goto, S. Ito, S. Natori, S. Nozoe (Eds.), Natural Products Chemistry, vols. 1-3, Kodansha, Tokyo, 1974.
3. [3]
  [3] F.M. Dean, Recent advances in furan chemistry. Part Ⅱ, in: A.R. Katritzky (Ed.), Advances in Heterocyclic Chemistry, vol. 31, Academic Press,NewYork, 1983, p.237.
4. [4]
  [4] M.V. Sargent, F.M. Dean, Furans and their benzo derivatives: (ii) reactivity, in: C.W. Bird, G.W.H. Cheeseman (Eds.), Comprehensive Heterocyclic Chemistry, vol. 3, Pergamon Press, Oxford, 1984, p. 599.
5. [5]
  [5] B.H. Lipshutz, Five-membered heteroaromatic rings as intermediates in organic synthesis, Chem. Rev. 86 (1986) 795-819.
6. [6]
  [6] I. Bock, H. Bornowski, A. Ranft, H. Theis, New aspects in the synthesis of mono-and dialkylfurans, Tetrahedron 46 (1990) 1199-1210.
7. [7]
  [7] D.S. Mortensen, A.L. Rodriguez, K.E. Carlson, et al., Synthesis and biological evaluation of a novel series of furans: ligands selective for estrogen receptor a, J. Med. Chem. 44 (2001) 3838-3848.
8. [8]
  [8] M. Naim, I. Zuker, U. Zehavi, R.L. Rouseff, Inhibition by thiol compounds of offflavor formation in stored orange juice 2. Effect of L-cysteine and N-acetyl-Lcysteine on p-vinylguaiacol formation, J. Agric. Food Chem. 41 (1993) 1359-1361.
9. [9]
  [9] R. Benassi, Furans and their benzo derivatives: structure, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 2, Pergamon Press, Oxford, 1996, p. 259.
10. [10]
  [10] H. Heaney, J.S. Ahn, Furans and their benzo derivatives: reactivity, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 29, Pergamon Press, Oxford, 1996, p. 297.
11. [11]
  [11] W. Friedrichsen, Furans and their benzo derivatives: synthesis, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 2, Pergamon Press, Oxford, 1996, p. 351.
12. [12]
  [12] B.A. Keay, P.W. Dibble, Furans and their benzo derivatives: applications, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 2, Pergamon Press, Oxford, 1996, p. 395.
13. [13]
  [13] B.M. Trost, I. Fleming, Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991.
14. [14]
  [14] A.I. Meyers, Heterocycles in Organic Synthesis, Wiley-Interscience, New York, 1974.
15. [15]
  [15] X.L. Hou, Z. Yang, H.N.C. Wong, Five-membered ring systems: furans and benzofurans, in: G.W. Gribble, T.L. Gilchrist (Eds.), The Structure, Reactions, Synthesis, and Uses of Heterocyclic Compounds, Progress in Heterocyclic Chemistry, vol. 14, Pergamon Press, Oxford, 2002, p. 139.
16. [16]
  [16] X.L. Hou, H.Y. Cheung, T.Y. Hon, et al., Regioselective syntheses of substituted furans, Tetrahedron 54 (1998) 1955-2020.
17. [17]
  [17] R. Cao, C. Liu, L. Liu, A convenient synthesis of 2(5H)-furanose, Org. Prep. Proc. Int. 28 (1996) 215-216.
18. [18]
  [18] C. Fu, S. Ma, Efficient preparation of 4-iodofuran-2(5H)-ones by iodolactonisation of 2,3-allenoates with I2, Eur. J. Org. Chem. 2005 (2005) 3942-3945.
19. [19]
  [19] (a) G.J. Hollingworth, G. Perkins, J.B. Sweeney, Preparation and palladium-catalysed cross-coupling reactions of 3-and 4-tributylstannylfuran-2(5H)-ones, J. Chem. Soc. Perkin Trans. 1 (1996) 1913-1917;
20. [20]
  (b) R. Mabon, A.M.E. Richecoeur, J.B. Sweeney, Preparation and reactions of 3,4-bis(tributylstannyl)-2(5H)-furanone, J. Org. Chem. 64 (1999) 328-329;
21. [21]
  (c) R. Mabon, A.M.E. Richecoeur, J.B. Sweeney, Preparation and reactions of 3,4-bisstannyl-2(5H)furanones, Tetrahedron 58 (2002) 9117-9129.
22. [22]
  [20] M. Bassetti, A. D'Annibale, A. Fanfoni, F. Minissi, Synthesis of a,b-unsaturated 4, 5-disubstituted g-lactones via ring-closing metathesis catalyzed by the firstgeneration Grubbs' catalyst, Org. Lett. 7 (2005) 1805-1808.
23. [23]
  [21] S. Narayana Murthy, B. Madhav, A. Vijay Kumar, K. Rama Rao, Y.V.D. Nageswar, Facile and efficient synthesis of 3,4,5-substituted furan-2(5H)-ones by using bcyclodextrin as reusable catalyst, Tetrahedron 65 (2009) 5251-5256.
24. [24]
  [22] R. Subburethinam, N. Rajagopal, Efficient one-pot multicomponent synthesis of (carbazolylamino)furan-2(5H)-one and carbazolyltetrahydropyrimidine derivatives, Synthesis 20 (2011) 3307-3317.
25. [25]
  [23] L. Nagarapu, U. Nikhil Kumar, P. Upendra, R. Bantu, Simple, convenient method for the synthesis of substituted furan-2(5H)-one derivatives using Tin(Ⅱ) chloride, Synth. Commun. 42 (2012) 2139-2148.
26. [26]
  [24] R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, Acetic acid as an efficient catalyst for the one-pot preparation of 3,4,5-substituted furan-2(5H)-ones, Res. Chem. Intermed. (2013), http://dx.doi.org/10.1007/s11164-012-0922-1 (This article is being published).
27. [27]
  [25] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, G. Marandi, M. Nassiri, g-Spiroiminolactone synthesis by reaction of acetylenic esters and a-dicarbonyl compounds in the presence of aryl isocyanide, Synth. Commun. 35 (2005) 2771-2777.
28. [28]
  [26] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, et al., Reaction of alkyl and aryl Isocyanides with floren-9-ones in the presence of acetylenic esters: preparation of g-spiroiminolactones, Synth. Commun. 35 (2005) 2569-2574.
29. [29]
  [27] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, G. Marandi, M. Nassiri, 1, 8-Diazafloren-9-one with alkyl and aryl isocyanides in the presence of acetylenic esters: a facile synthesis of g-spiroiminolactones, J. Heterocycl Chem. 43 (2006) 481-484.
30. [30]
  [28] N. Hazeri, M.T. Maghsoodlou, R. Heydari, et al., g-Dispiro-iminolactone synthesis by three component reaction between alkyl isocyanides and acetylenic esters with a-dicarbonyl compounds, ARKIVOC xiii (2007) 34-40.
31. [31]
  [29] N. Hazeri, M.T. Maghsoodlou, R. Heydari, et al., Synthesis of novel 2-pyridylsubstituted 2,5-dihydro-2-imino-and 2-amino-furan derivatives via a three component condensation of alkyl isocyanides and acetylenic esters with di-(2-pyridyl) ketone or 2-pyridinecarboxaldehyde, ARKIVOC i (2007) 173-179.
32. [32]
  [30] F. Rostami-Charati, M.T. Maghsoodlou, S.M. Habibi Khorassani, R. Heydari, M. Makha, Green diastereoselective synthesis of highly functionalised trifluoromethylated c-lactone phosphonate esters bearing a thioester or ketothiophene, Tetrahedron Lett. 49 (2008) 343-347.
33. [33]
  [31] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, et al., Diastereoselective synthesis of g-ispiroiminolactone bearing naphthalene or bipyridine pendant groups, J. Heterocycl. Chem. 46 (2009) 843-848.
34. [34]
  [32] M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Moradi, et al., One-pot threecomponent synthesis of functionalized spirolactones by means of reaction between aromatic ketones, dimethyl acetylenedicarboxylate, and N-heterocycles, Tetrahedron 67 (2011) 8492-8495.
35. [35]
  [33] M.T. Maghsoodlou, G. Marandi, N. Hazeri, S.M. Habibi-Khorassani, A.A. Mirzaei, Synthesis of 5-aryl-1,3-dimethyl-6-(alkyl-or aryl-amino)furo[2,3-d] pyrimidine derivatives by reaction between isocyanides and pyridinecarbaldehydes in the presence of 1,3-dimethylbarbituric acid,Mol. Divers. 15 (2011) 227-231.
1. [1]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
2. [2]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
3. [3]
  An Lu , Yuhao Guo , Yi Yan , Lin Zhai , Xiangyu Wang , Weiran Cao , Zijie Li , Zhixia Zhao , Yujie Shi , Yuanjun Zhu , Xiaoyan Liu , Huining He , Zhiyu Wang , Jian-Cheng Wang . Nanomedicine integrating the lipidic derivative of 5-fluorouracil, miriplatin and PD-L1 siRNA for enhancing tumor therapy. Chinese Chemical Letters, 2024, 35(6): 108928-. doi: 10.1016/j.cclet.2023.108928
4. [4]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
5. [5]
  Luyan Shi , Ke Zhu , Yuting Yang , Qinrui Liang , Qimin Peng , Shuqing Zhou , Tayirjan Taylor Isimjan , Xiulin Yang . Phytic acid-derivative Co₂B-CoPO_x coralloidal structure with delicate boron vacancy for enhanced hydrogen generation from sodium borohydride. Chinese Chemical Letters, 2024, 35(4): 109222-. doi: 10.1016/j.cclet.2023.109222
6. [6]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
7. [7]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
8. [8]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
9. [9]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
10. [10]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
11. [11]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C₃N₄纳米片及其高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
12. [12]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
13. [13]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
14. [14]
  Entian Cui , Yulian Lu , Zhaoxia Li , Zhilei Chen , Chengyan Ge , Jizhou Jiang . Interfacial B-O bonding modulated S-scheme B-doped N-deficient C₃N₄/O-doped-C₃N₅ for efficient photocatalytic overall water splitting. Chinese Chemical Letters, 2025, 36(1): 110288-. doi: 10.1016/j.cclet.2024.110288
15. [15]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
16. [16]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
17. [17]
  Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
18. [18]
  Dongying Fu , Lin Pan , Yanli Ma , Yue Zhang . Bilayered Dion–Jacobson lead-iodine hybrid perovskite with aromatic spacer for broadband photodetection. Chinese Chemical Letters, 2025, 36(2): 109621-. doi: 10.1016/j.cclet.2024.109621
19. [19]
  Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag₃PO₄/C₃N₅ Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-. doi: 10.3866/PKU.WHXB202310013
20. [20]
  Zhi Zhu , Xiaohan Xing , Qi Qi , Wenjing Shen , Hongyue Wu , Dongyi Li , Binrong Li , Jialin Liang , Xu Tang , Jun Zhao , Hongping Li , Pengwei Huo . Fabrication of graphene modified CeO2/g-C3N4 heterostructures for photocatalytic degradation of organic pollutants. Chinese Journal of Structural Chemistry, 2023, 42(12): 100194-100194. doi: 10.1016/j.cjsc.2023.100194

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(655)
HTML views(6)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142