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- 2016
水相中离子液体[ADPQ][BF4]催化“一锅法”合成四氢苯并[b]吡喃
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Abstract:
摘要 目的：制备1种以4-氨基奎宁为基础的离子液体,催化3组分一锅法制备四氢苯并吡喃的反应.方法：以水为溶剂,反应底物为芳香醛、活性亚甲基化合物和双甲酮.结果：最佳反应条件为:催化剂用量为芳香醛摩尔量的15%,反应温度为60℃,以水做溶剂.在此条件下,尝试的底物反应时间均在2 h内,收率为83%~96%.结论：该催化体系反应条件温和,时间短,收率高,反应后处理简单,催化剂重复使用4次催化效果变化不大.
| [1] | DOMLING A. Recent developments in isocyanide based multicomponent reactions in applied chemistry[J]. Chemical reviews, 2006, 106(1): 17-89. |
| [2] | SABITHA G, ARUNDHATHI K, SUDHAKAR K, et al. Cerium (III) chloride-catalyzed one-pot synthesis of tetrahydrobenzo [b] pyrans[J]. Synthetic Communications ® , 2009, 39(3): 433-442. |
| [3] | HAZERI N, MAGHSOODLOU M T, MIR F, et al. An efficient one-pot three-component synthesis of tetrahydrobenzo [b] pyran and 3, 4-dihydropyrano [c] chromene derivatives using starch solution as catalyst[J]. Chinese Journal of Catalysis, 2014, 35(3): 391-395. |
| [4] | BALALAIE S, SHEIKH-AHMADI M, BARARJANIAN M. Tetra-methyl ammonium hydroxide: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo [b] pyran derivatives in aqueous media[J]. Catalysis Communications, 2007, 8(11): 1724-1728. |
| [5] | SEIFI M, SHEIBANI H. High surface area MgO as a highly effective heterogeneous base catalyst for three-component synthesis of tetrahydrobenzopyran and 3, 4-dihydropyrano [c] chromene derivatives in aqueous media[J]. Catalysis letters, 2008, 126(3/4): 275-279. |
| [6] | KHAKSAR S, ROUHOLLAHPOUR A, TALESH S M. 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]. Journal of Fluorine Chemistry, 2012, 141(14): 11-15. |
| [7] | GAO X C, GAO R C. [ADPQ][CH3COO]: efficient and recyclable catalyst for aza-Michael addition of a, b-unsaturated compounds and amines under solvent-free conditions. Research on Chemical Intermediates, 2015, 41(11): 9101-9112. |
| [8] | YU L Q, LIU F, YOU Q D. One-pot synthesis of tetrahydrobenzo [b] pyran derivatives catalyzed by amines in aqueous media[J]. Organic Preparations and Procedures International, 2009, 41(1): 77-82. |
| [9] | XU J C, LI W M, ZHENG H, et al. One-pot synthesis of tetrahydrochromene derivatives catalyzed by lipase[J]. Tetrahedron, 2011, 67(49): 9582-9587. |
| [10] | ANANDGAONKER P L, JADHAV S, GAIKWAD S T, et al. Nanosized TiO2 as a recyclable heterogeneous catalyst for the synthesis of tetrahydrobenzo [b] pyran derivatives[J]. Journal of Cluster Science, 2014, 25(2): 483-493. |
| [11] | DEVI I, BHUYAN P J. Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo [b] pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions[J]. Tetrahedron Letters, 2004, 45(47): 8625-8627. |
| [12] | LI J T, XU W Z, YANG L C, et al. 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[J]. Synthetic communications, 2004, 34(24): 4565-4571. |
| [13] | FOTOUHI L, HERAVI M M, FATEHI A, et al. Electrogenerated base-promoted synthesis of tetrahydrobenzo [b] pyran derivatives[J]. Tetrahedron letters, 2007, 48(31): 5379-5381. |
| [14] | HASANINEJAD A, SHEKOUHY M, GOLZAR N, et al. 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[J]. Applied Catalysis A: General, 2011, 402(1): 11-22. |
| [15] | GAO S, TSAI C H, TSENG C, et al. Fluoride ion catalyzed multicomponent reactions for efficient synthesis of 4H-chromene and N-arylquinoline derivatives in aqueous media[J]. Tetrahedron, 2008, 64(38): 9143-9149. |
| [16] | MOBINIKHALEDI A, FARD M A B. Tetrabutylammonium bromide in water as a green media for the synthesis of pyrano [2, 3-d] pyrimidinone and tetrahydrobenzo [b] pyran derivatives[J]. Acta Chimica. Slovenica, 2010, 57(4): 931-935. |
| [17] | ZHENG J, LI Y. Basic ionic liquid-catalyzed multicomponent synthesis of tetrahydrobenzo [b] pyrans and pyrano [c] chromenes[J]. Mendeleev Communications, 2011, 21(5): 280-281. |
| [18] | WANG Y L, LI Z, LUO J, et al. One-pot synthesis of Tetrahydrobenzo [b] pyrans catalyzed by PEG-1000 bridged primary amine functionalized dicationic ionic liquid in water[J]. Journal of the Chinese Chemical Society, 2013, 60(12): 1431-1436. |
| [19] | MOOSAVI-ZARE A R, ZOLFIGOL M A, KHALEDIAN O, et al. Tandem Knoevenagel-Michael-cyclocondensation reactions of malononitrile, various aldehydes and dimedone using acetic acid functionalized ionic liquid[J]. New Journal of Chemistry, 2014, 38(6): 2342-2347. |
| [20] | BONSIGNORE L, LOY G, SECCI D, et al. Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives[J]. European Journal of Medicinal Chemistry, 1993, 28(6): 517-520. |
| [21] | THOMPSON R, DOGGRELL S, HOBERG J O. Potassium channel activators based on the benzopyran substructure: Synthesis and activity of the C-8 substituent[J]. Bioorganic & medicinal chemistry, 2003, 11(8): 1663-1668. |
| [22] | TANG L, YU J, LENG Y, et al. Synthesis and insulin-sensitizing activity of a novel kind of benzopyran derivative[J]. Bioorganic & medicinal chemistry letters, 2003, 13(20): 3437-3440. |
| [23] | ARMETSO D, HORSPOOL W M, MARTIN N, et al. Synthesis of cyclobutenes by the novel photochemical ring contraction of 4-substituted, 2-amino-3, 5-dicyano-6-phenyl-4H-pyrans[J]. J. Org. Chem., 1989, 54(13): 3069-3072. |
| [24] | SALVI P P, MANDHARE A M, SARTAPE A S, et al. An efficient protocol for synthesis of tetrahydrobenzo[b]pyrans using amino functionalized ionic liquid[J]. C. R. Chimie, 2011, 14(10): 878-882. |
| [25] | GAO X C, GAO C, GAO R C. Knoevenagel condensation reaction using ionic liquid [ADPQ][CF3SO3] as green and reusable catalyst. Asian Journal of Chemistry, 2015, 27(6): 2145-2148. |
| [26] | ZHI H, LV C, ZHANG Q, et al. A new PEG-1000-based dicationic ionic liquid exhibiting temperature-dependent phase behavior with toluene and its application in one-pot synthesis of benzopyrans[J]. Chem. Commun., 2009, 40(41): 2878-2880. |
| [27] | MOSADDEGH E, HASSANKHANI A, MANSOURI G. An efficient, simple and green Zn (Phen) 2Cl2 complex catalyzed synthesis of 4-H-benzo [b] pyrans in water at ambient temperature[J]. Journal of Chemistry, 2011, 8(2): 529-534. |
| [28] | KHAN A T, LAL M, ALI S, et al. One-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalyst[J]. Tetrahedron Letters, 2011, 52(41): 5327-5332. |
| [29] | SHATERIAN H R, ARMAN M, RIGI F. Domino Knoevenagel condensation, Michael addition, and cyclization using ionic liquid, 2-hydroxyethylammonium formate, as a recoverable catalyst[J]. Journal of Molecular Liquids, 2011, 158(2): 145-150. |
| [30] | ROSTAMNIA S, HASSANKHANI A, HOSSIENI H G, et al. Brønsted acidic hydrogensulfate ionic liquid immobilized SBA-15:[MPIm][HSO4]@SBA-15 as an environmentally friendly, metal-and halogen-free recyclable catalyst for Knoevenagel-Michael- cyclization processes[J]. Journal of Molecular Catalysis A: Chemical, 2014, 395: 463-469. |
