Synthesis of pyranopyrazoles, benzopyrans, amino-2-chromenes and dihydropyrano[c]chromenes using ionic liquid with dual Brønsted acidic and Lewis basic sites
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An efficient ionic liquid with both Brønsted acidic and Lewis basic sites, namely 1,4-dimethyl-1-(4-sulphobutyl)piperazinium hydrogen sulphate (IL1), was synthesised and characterised. IL1 is a “green”, homogeneous and reusable catalyst for: i) the synthesis of pyranopyrazoles (Va-Vj)and benzopyrans (VIa-VIj and VIIa-VIIf) at ambient temperature under solvent-free conditions and ii) the synthesis of amino-2-chromenes (VIIIa-VIIIi and IXa-IXi) and dihyropyrano[c]chromenes (Xa-Xi) at 80 °C under solvent-free conditions. The reactions were rapid with excellent product yields. In addition, the double Brønsted acid, 1,4-dimethyl-1,4-bis(4-sulphobutyl)piperazinium hydrogen sulphate (IL2), was prepared to evaluate the cooperation efficiency of their Brønsted acidic and Lewis basic sites as compared with the double Brønsted acidic sites in IL1.
Keywordsionic liquid synthesis pyranopyrazoles benzopyrans amino-2-chromenes dihydropyrano[c]chromenes
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- Al’-Assar, F., Zelenin, K. N., Lesiovskaya, E. E., Bezhan, I. P., & Chakchir, B. A. (2002). Synthesis and pharmacological activity of 1-hydroxy-1-amino-, and 1-hydrazino-substituted 2,3-dihydro-1H-pyrazolo[1,2-a]pyridazine-5,8-diones. Pharmaceutical Chemistry Journal, 36, 598–603. DOI: 10.1023/a:1022665331722.CrossRefGoogle Scholar
- Banerjee, S., Horn, A., Khatri, H., & Sereda, G. (2011). A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst. Tetrahedron Letters, 52, 1878–1881. DOI: 10.1016/j.tetlet.2011.02.031.CrossRefGoogle Scholar
- Chen, L., Li, Y. Q., Huang, X. J., & Zheng, W. J. (2009). N, N-dimethylamino-functionalized basic ionic liquid catalyzed one-pot multicomponent reaction for the synthesis of 4H-benzo[b]pyran derivatives under solvent-free condition. Heteroatom Chemistry, 20, 91–94. DOI: 10.1002/hc.20516.CrossRefGoogle Scholar
- Firouzabadi, H., Iranpoor, N., Jafarpour, M., & Ghaderi, A. (2006). ZrOCl2·8H2O/silica gel as a new efficient and a highly water-tolerant catalyst system for facile condensation of indoles with carbonyl compounds under solvent-free conditions. Journal of Molecular Catalysis A: Chemical, 253, 249–251. DOI: 10.1016/j.molcata.2006.03.043.CrossRefGoogle Scholar
- Hasaninejad, A., Shekouhy, M., Golzar, N., Zare, A., & Doroodmand, M. M. (2011). 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. Applied Catalysis A: General, 402, 11–22. DOI: 10.1016/j.apcata.2011.04.012.CrossRefGoogle Scholar
- Heravi, M. M., Jani, B. A., Derikvand, F., Bamoharram, F. F., & Oskooie, H. A. (2008). Three component, one-pot synthesis of dihydropyrano[3,2-c]chromene derivatives in the presence of H6P2W18O62 · 18H2O as a green and recyclable catalyst. Catalysis Communications, 10, 272–275. DOI: 10.1016/j.catcom.2008.08.023.CrossRefGoogle Scholar
- Jiménez-González, C., & Constable, D. J. C. (2011). Green chemistry and engineering: A practical design approach. Hoboken, NJ, USA: Wiley.Google Scholar
- Khurana, J. M., & Kumar, S. (2009). Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions. Tetrahedron Letters, 50, 4125–4127. DOI: 10.1016/j.tetlet.2009.04.125.CrossRefGoogle Scholar
- Konkoy, C. S., Fick, D. B., Cai, S. X., Lan, N. C., & Keana, J. F. W. (2000). WO Patent No. 2000075123 (A1). Geneva, Switzerland: World Intellectual Property Organization.Google Scholar
- Ranu, B. C., Banerjee, S., & Roy, S. (2008). A task specific basic ionic liquid, [bmIm]OH-promoted efficient, green and one-pot synthesis of tetrahydrobenzo[b]pyran derivatives. Indian Journal of Chemistry Section B: Organic Chemistry Including Medicinal Chemistry, 47, 1108–1112.Google Scholar