One-pot three-component synthesis of tetrahydrobenzo[b]pyrans catalyzed by cost-effective ionic liquid in aqueous medium

doi:10.1016/j.cjche.2015.04.020

Chinese Journal of Chemical Engineering ›› 2015, Vol. 23 ›› Issue (8): 1416-1420.DOI: 10.1016/j.cjche.2015.04.020

• 研究简报 • 上一篇

One-pot three-component synthesis of tetrahydrobenzo[b]pyrans catalyzed by cost-effective ionic liquid in aqueous medium

Jianguo Yang¹, Shuo Liu², Huanan Hu¹, Shibin Ren¹, Anguo Ying¹

1 School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China;
2 College of Chemistry, Nankai University, Tianjin 300071, China

收稿日期:2014-12-29 修回日期:2015-04-14 出版日期:2015-08-28 发布日期:2015-09-26
通讯作者: Anguo Ying
基金资助:
Supported by the Zhejiang Provincial Natural Science Foundation of China (LY15B060002), the National Natural Science Foundation of China (21106090, 21272169, 21471110), and the National Undergraduate Programs for Innovation and Entrepreneurship (201410350018).

One-pot three-component synthesis of tetrahydrobenzo[b]pyrans catalyzed by cost-effective ionic liquid in aqueous medium

Jianguo Yang¹, Shuo Liu², Huanan Hu¹, Shibin Ren¹, Anguo Ying¹

1 School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China;
2 College of Chemistry, Nankai University, Tianjin 300071, China

Received:2014-12-29 Revised:2015-04-14 Online:2015-08-28 Published:2015-09-26
Contact: Anguo Ying
Supported by:
Supported by the Zhejiang Provincial Natural Science Foundation of China (LY15B060002), the National Natural Science Foundation of China (21106090, 21272169, 21471110), and the National Undergraduate Programs for Innovation and Entrepreneurship (201410350018).

摘要/Abstract

摘要： A simple and efficient method is proposed for the synthesis of tetrahydrobenzo[b]pyrans with aromatic aldehydes, active methylene compounds, and dimedone using basic ionic liquid catalyst in water. The procedure offers several advantages including short reaction time, good yield, easy procedure, and good recyclability of catalysts, which may be a practical alternative to conventional processes for preparation of 4-hpyrans.

关键词: Tetrahydrobenzo[b]pyrans, Ionic liquid, Recyclability

Abstract: A simple and efficient method is proposed for the synthesis of tetrahydrobenzo[b]pyrans with aromatic aldehydes, active methylene compounds, and dimedone using basic ionic liquid catalyst in water. The procedure offers several advantages including short reaction time, good yield, easy procedure, and good recyclability of catalysts, which may be a practical alternative to conventional processes for preparation of 4-hpyrans.

Key words: Tetrahydrobenzo[b]pyrans, Ionic liquid, Recyclability

Jianguo Yang, Shuo Liu, Huanan Hu, Shibin Ren, Anguo Ying. One-pot three-component synthesis of tetrahydrobenzo[b]pyrans catalyzed by cost-effective ionic liquid in aqueous medium[J]. Chinese Journal of Chemical Engineering, 2015, 23(8): 1416-1420.

参考文献

[1] L. Bonsignore, A. Delogu, G. Loy, Synthesis and antimicrobial activity of coumarin and benzodioxazepine-substituted, diazazepine-substituted and benzoxazepinesubstituted penicillins, Eur. J. Med. Chem. 28(1993) 479-485.

[2] N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, An efficient one-pot three-component synthesis of tetrahydrobenzo[b]pyran and 3,4-dihydropyrano[c] chromene derivatives using starch solution as catalyst, Chin. J. Catal. 35(2014) 391-395.

[3] A. Saini, S. Kumar, J.S. Sandhu, A newLiBr-catalyzed, facile and efficient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j]xanthenes and tetrahydrobenzo[b]pyrans under solvent-free conventional and microwave heating, Synlett 12(2006) 1928-1932.

[4] G. Pandey, R.P. Singh, A. Gary, V.K. Singh, Nucleophilic displacement by azide and cyanide on Baylis-Hillman acetates in water, Tetrahedron Lett. 46(2005) 2137-2140.

[5] R. Thompson, S. Doggrell, J.O. Hoverg, Potassium channel activators based on the benzopyran substructure:synthesis and activity of the C-8 substituent, Bioorg. Med. Chem. 11(2003) 1663-1668.

[6] L. Tang, J.H. Yu, Y. Leng, Y. Feng, Y.S. Yang, R.Y. Ji, Synthesis and insulin-sensitizing activity of a novel kind of benzopyran derivative, Bioorg. Med. Chem. Lett. 13(2003) 3437-3440.

[7] K. Singh, J. Singh, H. Singh, A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles, Tetrahedron 52(1996) 14273-14280.

[8] A. Domling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 17(2006) 17-89.

[9] L. Weber, K. Illegen, M. Almstetter, Discovery of new multi component reactions with combinatorial methods, Synlett 3(1999) 366-374.

[10] G. Sabitha, K. Arundhathi, K. Sudhakar, B.S. Sastry, J.S. Yadav, Cerium (III) chloride-catalyzed one-pot synthesis of tetrahydrobenzo[b] pyrans, Synth. Commun. 39(2009) 433-442.

[11] X.Z. Lian, Y. Huang, Y.Q. Li,W.J. Zheng, A green synthesis of tetrahydrobenzo[b]pyran derivatives through three-component condensation using N-methylimidazole as organocatalyst, Monatsh. Chem. 139(2008) 129-131.

[12] B. Saeed, S. Masoumeh, B. Morteza, Tetra-methyl ammonium hydroxide:An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media, Catal. Commun. 8(2007) 1724-1728.

[13] M. Seifi, H. Sheibani, High surface areaMgO as a highly effective heterogeneous base catalyst for three-component synthesis of tetrahydrobenzopyran and 3,4-dihydropyrano[c]chromene derivatives in aqueous media, Catal. Lett. 126(2008) 275-279.

[14] L.Q. Yu, F. Liu, Q.D. You, One-pot synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by amines in aqueous media, Org. Prep. Proced. Int. 41(2009) 77-82.

[15] S. Khaksar, A. Rouhollahpour, S.M. Talesh, A facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans using 2, 2, 2-trifluoroethanol as a metal-free and reusable medium, J. Fluor. Chem. 141(2012) 11-15.

[16] L.A. Priyanka, S. Jadhav, S.T. Gaikwad, A.S. Rajbhoj, Nanosized TiO₂ as a recyclable heterogeneous catalyst for the synthesis of tetrahydrobenzo[b]pyran derivatives, J. Clust. Sci. 25(2014) 483-493.

[17] I. Devi, P.J. Bhuyan, Sodiumbromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions, Tetrahedron Lett. 45(2004) 8625-8627.

[18] J.T. Li,W.Z. Xu, L.C. Yang, T.S. Li, One-pot synthesis of 2-amino-4-aryl-3-carbalkoxy-7, 7-dimethyl-5, 6, 7, 8-tetrahydrobenzo[b]pyran derivatives catalyzed by KF/basic Al₂O₃ under ultrasound irradiation, Synth. Commun. 34(2004) 4565-4571.

[19] L. Fotouhi, M.M. Heravi, A. Fatehi, K. Bakhtiari, Electrogenerated base-promoted synthesis of tetrahydrobenzo[b]pyran derivatives, Tetrahedron Lett. 48(2007) 5379-5381.

[20] W.S. Miao, T.H. Chan, Ionic-liquid-supported synthesis:a novel liquid-phase strategy for organic synthesis, Acc. Chem. Res. 39(2006) 897-908.

[21] Y.L. Li, B.X. Du, X.S. Wang, D.Q. Shi, S.J. Tu, Synthesis of 2-amino-4-aryl-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran derivatives in ionic liquid medium, J. Heterocycl. Chem. 43(2006) 685-688.

[22] J. Zheng, Y.Q. Li, Basic ionic liquid-catalyzed multicomponent synthesis of tetrahydrobenzo[b]pyrans and pyrano[c]chromenes, Mendeleev Commun. 21(2011) 280-281.

[23] L.R. Wen, H.Y. Xie, M. Li, A basic ionic liquid catalyzed reaction of benzothiazole, aldehydes, and 5,5-dimethyl-1,3-cyclohexanedione:efficient synthesis of tetrahydrobenzo[b]pyrans, J. Heterocycl. Chem. 46(2009) 954-959.

[24] Y.L. Wang, Z. Li, J. Luo, Z.L. Liu, One-pot synthesis of tetrahydrobenzo[b]pyrans catalyzed by PEG-1000 bridged primary amine functionalized dicationic ionic liquid in water, J. Chin. Chem. Soc. 60(2013) 1431-1436.

[25] A.G. Ying, Y.X. Ni, S.L. Xu, S. Liu, J.G. Yang, R.R. Li, Novel DABCO based ionic liquids:Green and efficient catalysts with dual catalytic roles f or aqueous Knoevenagel condensation, Ind. Eng. Chem. Res. 53(2014) 5678-5682.

[26] H.N. Hu, F.L. Qiu, A.G. Ying, J.G. Yang, H.P.Meng, An environmentally benign protocol for aqueous synthesis of tetrahydrobenzo[b]pyrans catalyzed by cost-effective ionic liquid, Int. J. Mol. Sci. 15(2014) 6897-6909.

[27] A.G. Ying, Z.F. Li, J.G. Yang, S. Liu, S.L. Xu, H. Yan, C.L.Wu, DABCO-based ionic liquids:Recyclable catalysts for Aza-Michael addition of alpha, beta-unsaturated amides under solvent-free conditions, J. Org. Chem. 79(2014) 6510-6516.

[28] J.C. Xu,W.M. Li,H. Zheng, Y.F. Lai, P.F. Zhang,One-pot synthesis of tetrahydrochromene derivatives catalyzed by lipase, Tetrahedron 67(2011) 9582-9587.

[29] H.Z. Zhi, C.X. Lv, Q. Zhang, A new PEG-1000-based dicationic ionic liquid exhibiting temperature-dependent phase behavior with toluene and its application in one-pot synthesis of benzofurans, Chem. Commun. 20(2009) 2878-2880.

[30] E. Mosaddegh, A. Hassankhani, G. Mansouri, An efficient, simple and green Zn(Phen)₂Cl₂ complex catalyzed synthesis of 4-H-benzo[b]pyrans inwater at ambient temperature, E-J. Chem. 8(2011) 529-534.

[31] A. Patra, T. Mahapatra, Synthesis of tetrahydrobenzo[b]pyran derivatives catalysed by Aliquat 336 in water under microwave irradiation, J. Chem. Res. 34(2010) 689-693.

[32] A. Hasaninejad, M. Shekouhy, N. Golzar, Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2] octane chloride (SB-DABCO):a highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H-benzo[b]pyran derivatives, Appl. Catal. A Gen. 402(2011) 11-22.

[33] S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Fluoride ion catalyzedmulticomponent reactions for efficient synthesis of 4H-chromene and N-arylquinoline derivatives in aqueous media, Tetrahedron 64(2008) 9143-9149.

[34] A.T. Khan, M. Lal, S. Ali, One-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalyst, Tetrahedron Lett. 52(2011) 5327-5332.

[35] D.Q. Shi, S. Zhang, X.S. Wang, Ethyl 2-amino-4-(4-fluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran-3-carboxylate, Acta Crystallogr. Sect. E:Struct. Rep. Online 59(2003) 1501-1502.

One-pot three-component synthesis of tetrahydrobenzo[b]pyrans catalyzed by cost-effective ionic liquid in aqueous medium

One-pot three-component synthesis of tetrahydrobenzo[b]pyrans catalyzed by cost-effective ionic liquid in aqueous medium

PDF (PC)

可视化

被引次数

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Eileen Katherine Coronado-Aldana, Cindy Lizeth Ferreira-Salazar, Nubia Yineth Piñeros-Castro, Rubén Vázquez-Medina, Felipe A. Perdomo. Thermodynamic analysis, synthesis, characterization, and evaluation of 1-ethyl-3-methylimidazolium chloride: Study of its effect on pretreated rice husk[J]. 中国化学工程学报, 2023, 60(8): 143-154.
[2]	Zhonghao Li, Yuanyuan Yang, Huanong Cheng, Yun Teng, Chao Li, Kangkang Li, Zhou Feng, Hongwei Jin, Xinshun Tan, Shiqing Zheng. Measurement and model of density, viscosity, and hydrogen sulfide solubility in ferric chloride/trioctylmethylammonium chloride ionic liquid[J]. 中国化学工程学报, 2023, 59(7): 210-221.
[3]	Chen Chen, Qiong Tang, Hong Xu, Mingxing Tang, Xuekuan Li, Lei Liu, Jinxiang Dong. Alkyl-tetralin base oils synthesized from coal-based chemicals and evaluation of their lubricating properties[J]. 中国化学工程学报, 2023, 58(6): 20-28.
[4]	Yutong Jiang, Yifeng Chen, Fuliu Yang, Jixue Fan, Jun Li, Zhuhong Yang, Xiaoyan Ji. Efficient SO₂ removal using aqueous ionic liquid at low partial pressure[J]. 中国化学工程学报, 2023, 58(6): 355-363.
[5]	Jialei Sha, Chenyi Liu, Zhihong Ma, Weizhong Zheng, Weizhen Sun, Ling Zhao. Understanding the interfacial behaviors of benzene alkylation with butene using chloroaluminate ionic liquid catalyst: A molecular dynamics simulation[J]. 中国化学工程学报, 2023, 54(2): 44-52.
[6]	Yifeng Chen, Hang Yu, Jingjing Chen, Xiaohua Lu, Xiaoyan Ji. Viscous behavior of 1-hexyl-methylimidazolium bis(trifluoromethylsulfonyl)imide/titanium dioxide/polyethylene glycol[J]. 中国化学工程学报, 2023, 54(2): 280-287.
[7]	Mi Feng, Bin He, Xinyan Chen, Junli Xu, Xingmei Lu, Cai Jia, Jian Sun. Separation of chitin from shrimp shells enabled by transition metal salt aqueous solution and ionic liquid[J]. 中国化学工程学报, 2023, 53(1): 133-141.
[8]	Xuan Gao, Zhihui Li, Dongsheng Zhang, Xinqiang Zhao, Yanji Wang. Synthesis and kinetics of 2,5-dicyanofuran in the presence of hydroxylamine ionic liquid salts[J]. 中国化学工程学报, 2023, 53(1): 310-316.
[9]	Xinqiang You, Kai Zhao, Ling Li, Ting Qiu. Ionic liquids as entrainer in extractive distillation for effectively separating 1-propanol–water azeotropic mixture[J]. 中国化学工程学报, 2022, 49(9): 224-233.
[10]	Minjie Shi, Hangtian Zhu, Cheng Yang, Jing Xu, Chao Yan. Chemical reduction-induced fabrication of graphene hybrid fibers for energy-dense wire-shaped supercapacitors[J]. 中国化学工程学报, 2022, 47(7): 1-10.
[11]	Song Hu, Jinlong Li, Qihua Wang, Weisheng Yang. Design and optimization of an integrated process for the purification of propylene oxide and the separation of propylene glycol by-product[J]. 中国化学工程学报, 2022, 45(5): 111-120.
[12]	Linlan Wu, Zhengxin Jiao, Suhang Xun, Minqiang He, Lei Fan, Chao Wang, Wenshu Yang, Wenshuai Zhu, Huaming Li. Photocatalytic oxidative of Keggin-type polyoxometalate ionic liquid for enhanced extractive desulfurization in binary deep eutectic solvents[J]. 中国化学工程学报, 2022, 44(4): 205-211.
[13]	Alireza Afsharpour. A new approach for correlating of H₂S solubility in [emim][Lac], [bmim][ac] and [emim][pro] ionic liquids using two-parts combined models[J]. 中国化学工程学报, 2022, 44(4): 521-527.
[14]	Haiyan Jiang, Lu Bai, Bingbing Yang, Shaojuan Zeng, Haifeng Dong, Xiangping Zhang. The effect of protic ionic liquids incorporation on CO₂ separation performance of Pebax-based membranes[J]. 中国化学工程学报, 2022, 43(3): 169-176.
[15]	Mingdong Sun, Zhengyun Bian, Weiwei Cui, Xiaolong Zhao, Shu Dong, Xuebin Ke, Yu Zhou, Jun Wang. Pyrolyzing soft template-containing poly(ionic liquid) into hierarchical N-doped porous carbon for electroreduction of carbon dioxide[J]. 中国化学工程学报, 2022, 43(3): 192-201.