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茚类衍生物的合成研究
Synthesis Studies of Indene Derivatives

DOI: 10.12677/jocr.2024.122035, PP. 365-378

Keywords: 茚类衍生物,多环芳烃,新型高效
Indene Derivatives
, Polycyclic Aromatic Hydrocarbon, New and Efficient

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Abstract:

茚是一种非常有用的多环芳烃,广泛存在于天然产物和药物分子中,在材料和金属催化等领域也有着广泛的应用。茚类衍生物的合成一直受到化学家的关注,迄今为止已有很多茚类衍生物的合成报道。因此,本文对近些年茚类衍生物的合成方法进行了综述,希望能为茚类衍生物的合成研究提供参考。
Indene is a highly useful polycyclic aromatic hydrocarbon that is commonly found in natural products and pharmaceutical molecules. It has a wide range of applications in the realms of materials science and metal catalysis. The synthesis of indene derivatives has long been a focus of chemists, and there have been numerous reports on the synthesis of various indene derivatives. Therefore, this paper reviews the synthetic methods of indene derivatives in recent years, hoping to provide a reference for the synthetic research of indene compounds.

References

[1]  Tian, X., Chaiworn, S., Xu, J., Vanthuyne, N., Baldridge, K.K. and Siegel, J.S. (2021) Thiophene Fused Indenocorannulenes: Synthesis, Variable Emission, and Exceptional Chiral Configurational Stability. Organic Chemistry Frontiers, 8, 3653-3658.
https://doi.org/10.1039/d1qo00596k
[2]  Kalita, G., Paul, D., Khatua, S. and Chatterjee, P.N. (2020) Para-Toluenesulfonic Acid Catalyzed Synthesis of Indenes via a Tandem Friedel-Crafts Alkylation/Hydroarylation of Tertiary Propargylic Alcohols with Electron-Rich Arenes. Catalysis Letters, 150, 2132-2139.
https://doi.org/10.1007/s10562-020-03220-0
[3]  Kharitonov, V.B., Muratov, D.V. and Loginov, D.A. (2019) Indenyl Complexes of Group 9 Metals: Synthetic and Catalytic Chemistry. Coordination Chemistry Reviews, 399, Article ID: 213027.
https://doi.org/10.1016/j.ccr.2019.213027
[4]  Trost, B.M. and Ryan, M.C. (2017) Indenylmetal Catalysis in Organic Synthesis. Angewandte Chemie International Edition, 56, 2862-2879.
https://doi.org/10.1002/anie.201609054
[5]  Koby, R.F., Schley, N.D. and Hanusa, T.P. (2021) Di(indenyl)beryllium. Angewandte Chemie International Edition, 60, 21174-21178.
https://doi.org/10.1002/anie.202107980
[6]  Yuan, J., Zhang, Y., Yu, H., Wang, C., Meng, S., Chen, J., et al. (2022) Transition Metal Complexes with Functionalized Indenyl Phosphine Ligands: Structures and Catalytic Properties. Organic & Biomolecular Chemistry, 20, 485-497.
https://doi.org/10.1039/d1ob01884a
[7]  Malenov, D.P. and Zari?, S.D. (2020) Stacking Interactions between Indenyl Ligands of Transition Metal Complexes: Crystallographic and Density Functional Study. Crystal Growth & Design, 20, 4491-4502.
https://doi.org/10.1021/acs.cgd.0c00303
[8]  Mondal, S., Dumur, F., Gigmes, D., Sibi, M.P., Bertrand, M.P. and Nechab, M. (2022) Enantioselective Radical Reactions Using Chiral Catalysts. Chemical Reviews, 122, 5842-5976.
https://doi.org/10.1021/acs.chemrev.1c00582
[9]  Wang, J., Zhou, Y., Zhang, L., Li, Z., Chen, X. and Liu, H. (2013) Asymmetric Michael Addition of N-tert-Butanesulfinyl Imidate with α,β-Unsaturated Diesters: Scope and Application to the Synthesis of Indanone Derivatives. Organic Letters, 15, 1508-1511.
https://doi.org/10.1021/ol400277h
[10]  Satyanarayana, G., Ramulu, B. and Niharika, P. (2015) Superacid-Promoted Dual C-C Bond Formation by Friedel-Crafts Alkylation/Acylation of Cinnamate Esters: Synthesis of Indanones. Synthesis, 47, 1255-1268.
https://doi.org/10.1055/s-0034-1380385
[11]  Fillion, E. and Fishlock, D. (2009) Scandium Triflate-Catalyzed Intramolecular Friedel-Crafts Acylation with Meldrum’s Acids: Insight into the Mechanism. Tetrahedron, 65, 6682-6695.
https://doi.org/10.1016/j.tet.2009.05.058
[12]  Wanibuchi, K., Hosoda, K., Ihara, M., Tajiri, K., Sakai, Y., Masui, H., et al. (2018) Indene Compounds Synthetically Derived from Vitamin D Have Selective Antibacterial Action on Helicobacter pylori. Lipids, 53, 393-401.
https://doi.org/10.1002/lipd.12043
[13]  Titov, A.A., Kobzev, M.S., Catto, M., Candia, M.D., Gambacorta, N., Denora, N., et al. (2021) Away from Flatness: Unprecedented Nitrogen-Bridged Cyclopenta[a]indene Derivatives as Novel Anti-Alzheimer Multitarget Agents. ACS Chemical Neuroscience, 12, 340-353.
https://doi.org/10.1021/acschemneuro.0c00706
[14]  Sanz Garcia, J., Gaschard, M., Navizet, I., Sahihi, M., Top, S., Wang, Y., et al. (2022) Inhibition of Cathepsin B by Ferrocenyl Indenes Highlights a New Pharmacological Facet of Ferrocifens. European Journal of Inorganic Chemistry, 2022, e202101075.
https://doi.org/10.1002/ejic.202101075
[15]  Guan, X., Luo, P., He, Q., Hu, Y. and Ying, H. (2016) Design, Synthesis and Evaluation of Indene Derivatives as Retinoic Acid Receptor α Agonists. Molecules, 22, Article No. 32.
https://doi.org/10.3390/molecules22010032
[16]  Kim, J.A., Yun, H., Choi, Y., Kim, J., Choi, S., Kwon, T., et al. (2018) Magnesium Phosphate Ceramics Incorporating a Novel Indene Compound Promote Osteoblast Differentiation in Vitro and Bone Regeneration in Vivo. Biomaterials, 157, 51-61.
https://doi.org/10.1016/j.biomaterials.2017.11.032
[17]  Xia, Z., Zhang, Z., Su, J., Zhang, Q., Fung, K., Lam, M., et al. (2010) Robust and Highly Efficient Blue Light-Emitting Hosts Based on Indene-Substituted Anthracene. Journal of Materials Chemistry, 20, 3768-3774.
https://doi.org/10.1039/c000092b
[18]  Du, M., Xiao, Y., Geng, Y., Chen, Y., Jiang, H., Dong, C., et al. (2022) Application of Indacenodiselenophene Central Core and Modulation of Terminal Group Interaction for High-Efficient P3HT-Based Organic Solar Cells. Journal of Materials Chemistry C, 10, 10114-10123.
https://doi.org/10.1039/d2tc01855a
[19]  Wilkinson, G., Rosenblum, M., Whiting, M.C. and Woodward, R.B. (1952) The Structure of Iron Bis-Cyclopentadienyl. Journal of the American Chemical Society, 74, 2125-2126.
https://doi.org/10.1021/ja01128a527
[20]  Lauher, J.W. and Hoffmann, R. (1976) Structure and Chemistry of Bis(cyclopentadienyl)-MLn Complexes. Journal of the American Chemical Society, 98, 1729-1742.
https://doi.org/10.1021/ja00423a017
[21]  McKnight, A.L. and Waymouth, R.M. (1998) Group 4 ansa-Cyclopentadienyl-Amido Catalysts for Olefin Polymerization. Chemical Reviews, 98, 2587-2598.
https://doi.org/10.1021/cr940442r
[22]  Kowaleski, R.M., Rheingold, A.L., Trogler, W.C. and Basolo, F. (1986) Synthesis and Structure of Dicarbonyl(.eta.3-Indenyl)(.eta.5-Indenyl)vanadium(II). An Unusual Slipped Ring in a Metal Radical. Journal of the American Chemical Society, 108, 2460-2461.
https://doi.org/10.1021/ja00269a062
[23]  Chen, Z. and Halterman, R.L. (1992) Enantioselective Catalytic Isomerization of an Unfunctionalized Achiral Alkene. Journal of the American Chemical Society, 114, 2276-2277.
https://doi.org/10.1021/ja00032a062
[24]  Negishi, E., Choueiry, D., Nguyen, T.B., Swanson, D.R., Suzuki, N. and Takahashi, T. (1994) Nonconcerted Paths for Reactions of Alkene-Zirconocene Complexes. Journal of the American Chemical Society, 116, 9751-9752.
https://doi.org/10.1021/ja00100a051
[25]  Colletti, S.L. and Halterman, R.L. (1992) Asymmetric Epoxidation of Unfunctionalized Alkenes Using the New C2-Symmetrical 1,1’-Binaphthyl-2,2’-Dimethylene-Bridged ansa-Bis(1-Indenyl)titanium Dichloride Catalyst. Tetrahedron Letters, 33, 1005-1008.
https://doi.org/10.1016/s0040-4039(00)91845-8
[26]  Erker, G., Aulbach, M., Knickmeier, M., Wingbermuehle, D., Krueger, C., Nolte, M., et al. (1993) The Role of Torsional Isomers of Planarly Chiral Nonbridged Bis(indenyl)metal Type Complexes in Stereoselective Propene Polymerization. Journal of the American Chemical Society, 115, 4590-4601.
https://doi.org/10.1021/ja00064a022
[27]  Kondakov, D.Y. and Negishi, E. (1995) Zirconium-Catalyzed Enantioselective Methylalumination of Monosubstituted Alkenes. Journal of the American Chemical Society, 117, 10771-10772.
https://doi.org/10.1021/ja00148a031
[28]  Negishi, E., Tan, Z., Liang, B. and Novak, T. (2004) An Efficient and General Route to Reduced Polypropionates via Zr-Catalyzed Asymmetric C-C Bond Formation. Proceedings of the National Academy of Sciences, 101, 5782-5787.
https://doi.org/10.1073/pnas.0307514101
[29]  Parfenova, L.V., Berestova, T.V., Tyumkina, T.V., Kovyazin, P.V., Khalilov, L.M., Whitby, R.J., et al. (2010) Enantioselectivity of Chiral Zirconocenes as Catalysts in Alkene Hydro-, Carbo-and Cycloalumination Reactions. Tetrahedron: Asymmetry, 21, 299-310.
https://doi.org/10.1016/j.tetasy.2010.01.001
[30]  Kondakov, D.Y. and Negishi, E. (1996) Zirconium-Catalyzed Enantioselective Alkylalumination of Monosubstituted Alkenes Proceeding via Noncyclic Mechanism. Journal of the American Chemical Society, 118, 1577-1578.
https://doi.org/10.1021/ja953655m
[31]  Liang, B., Novak, T., Tan, Z. and Negishi, E. (2006) Catalytic, Efficient, and syn-Selective Construction of Deoxypolypropionates and Other Chiral Compounds via Zr-Catalyzed Asymmetric Carboalumination of Allyl Alcohol. Journal of the American Chemical Society, 128, 2770-2771.
https://doi.org/10.1021/ja0530974
[32]  Singh, P.P., Reddy, P.B., Sawant, S.D., Koul, S., Taneja, S.C. and Kumar, H.M.S. (2006) Domino Synthesis of Indenols and Alkyl-Indene Ethers under Modified Vilsmeier Conditions. Tetrahedron Letters, 47, 7241-7243.
https://doi.org/10.1016/j.tetlet.2006.07.126
[33]  Basavaiah, D., Reddy, B.S. and Lingam, H. (2013) Baylis-Hillman Acetates in Carbocyclic Synthesis: A Convenient Protocol for Synthesis of Densely Substituted Indenes. Tetrahedron, 69, 1994-2003.
https://doi.org/10.1016/j.tet.2012.12.069
[34]  Xu, X., Shao, J., Hu, P., Hong, G., Fang, M. and Li, X. (2014) Palladium-Catalyzed Synthesis of Indene Derivatives via Intramolecular Allylic Arylation of Baylis-Hillman Acetates. Synlett, 25, 1009-1013.
https://doi.org/10.1055/s-0033-1340830
[35]  Liu, L., Fan, Y., He, Q., Zhang, Y., Zhang-Negrerie, D., Huang, J., et al. (2012) Synthesis of Functionalized Fluorescent Indenes from Electron-Rich α-Aryl Ketonitriles. The Journal of Organic Chemistry, 77, 3997-4004.
https://doi.org/10.1021/jo300367q
[36]  Wang, Z., Li, Y., Chen, F., Qian, P. and Cheng, J. (2021) The Intramolecular Reaction of Acetophenone n-Tosylhydrazone and Vinyl: Br?nsted Acid-Promoted Cationic Cyclization toward Polysubstituted Indenes. Chemical Communications, 57, 1810-1813.
https://doi.org/10.1039/d0cc07966a
[37]  Vicente, R., Tudela, E., Rodríguez, M.A., Suárez-Sobrino, á.L. and Ballesteros, A. (2022) Gold-Catalysed Rearrangement of Unconventional Cyclopropane-Tethered 1,5-Enynes. Chemical Communications, 58, 8206-8209.
https://doi.org/10.1039/d2cc02869g
[38]  Thilmany, P., Guarnieri-Ibá?ez, A., Jacob, C., Lacour, J. and Evano, G. (2021) Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides. ACS Organic & Inorganic Au, 2, 53-58.
https://doi.org/10.1021/acsorginorgau.1c00021
[39]  Yamazaki, S., Katayama, K., Wang, Z., Mikata, Y., Morimoto, T. and Ogawa, A. (2021) Sequential Knoevenagel Condensation/Cyclization for the Synthesis of Indene and Benzofulvene Derivatives. ACS Omega, 6, 28441-28454.
https://doi.org/10.1021/acsomega.1c05283
[40]  Zhao, X., Fan, C., He, J. and Luo, Y. (2022) Rh-Catalyzed [3+2] Annulation of Cyclic Ketimines and Alkynyl Chloride: A Strategy for Accessing Unsymmetrically Substituted and Highly Functionalizable Indenes. Organic Letters, 24, 9169-9173.
https://doi.org/10.1021/acs.orglett.2c02717
[41]  Deng, C., Jiang, L., Yao, J., Liang, Q., Miao, L., Li, C., et al. (2022) Rhodium(III)-Catalyzed Sequential Cyclization of n-Boc Hydrazones with Propargylic Monofluoroalkynes via C-H Activation/C-F Cleavage for the Synthesis of Spiro[cyclobutane-1,9’-indeno[1,2-α]indenes]. The Journal of Organic Chemistry, 87, 6105-6114.
https://doi.org/10.1021/acs.joc.2c00372
[42]  Wang, C., Wu, C., Yang, Y., Xing, J. and Dou, X. (2022) Rhodium-Catalyzed Formal [2+2+1] Annulation of Arylboronic Acids with Alkynes. Organic Chemistry Frontiers, 9, 6915-6919.
https://doi.org/10.1039/d2qo01464e
[43]  Zhang, T., Zhang, C., Lu, X., Peng, C., Zhang, Y., Zhu, X., et al. (2024) Synthesis of Silyl Indenes by Ruthenium-Catalyzed Aldehyde-And Acylsilane-Enabled C-H Alkylation/Cyclization. Organic & Biomolecular Chemistry, 22, 466-471.
https://doi.org/10.1039/d3ob01699d
[44]  Wei, D., Lu, H., Miao, H., Feng, C., Lin, G. and Liu, Y. (2023) Pd-Catalyzed Intermolecular Consecutive Double Heck Reaction “on Water” under Air: Facile Synthesis of Substituted Indenes. RSC Advances, 13, 19312-19316.
https://doi.org/10.1039/d3ra03510g
[45]  Sun, Y., Pan, J., Wang, X., Bu, X., Ma, M. and Xue, F. (2023) Rhodium-Catalyzed Asymmetric Annulation of Unactivated Alkynes with 3-(ortho-Boronated Aryl) Conjugated Enones: Enantioselective Synthesis of 2,3-Disubstituted Indenes. The Journal of Organic Chemistry, 88, 6140-6145.
https://doi.org/10.1021/acs.joc.2c02957

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