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

Abstract

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

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

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]. Chin.J.Chem.Eng., 2015, 23(8): 1416-1420.

References

[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.