Review
doi: 10.3390/molecules27185976.
Indane-1,3-Dione: From Synthetic Strategies to Applications
Affiliations
- PMID: 36144711
- PMCID: PMC9501146
- DOI: 10.3390/molecules27185976
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Review
Indane-1,3-Dione: From Synthetic Strategies to Applications
Molecules.
.
Abstract
Indane-1,3-dione is a versatile building block used in numerous applications ranging from biosensing, bioactivity, bioimaging to electronics or photopolymerization. In this review, an overview of the different chemical reactions enabling access to this scaffold but also to the most common derivatives of indane-1,3-dione are presented. Parallel to this, the different applications in which indane-1,3-dione-based structures have been used are also presented, evidencing the versatility of this structure.
Keywords: MCR; chemical modification; domino reaction; indanedione; spiro compounds.
Conflict of interest statement
The authors declare no conflict of interest.
Figures
Synthetic routes to indane-1,3-dione 4.
Synthetic routes to substituted indane-1,3-diones 19–21 and 25, 26.
Synthetic routes to 28, 31, 31′, 33, 33′, 35, 35′.
Synthetic routes to 37a–37d, 39, 41, 43, 45, 47 and 49.
Synthesis of bindone 50.
Synthetic route to bis-thiazoles and bis-thiazolidinone starting from 4.
Synthetic routes to 68, 72 and 75.
Examples of halogenated indane-1,3-diones 76–82, 84 reported in the literature.
Synthesis of nitro-substituted indane-1,3-diones 19 and 21.
Ethoxy-carbonyl compound 32.
Synthesis of push–pull dyes 95–114.
Mechanism resulting in the synthesis of 3-(dialkylamino)-1,2-dihydro-9-oxo-9H-indeno [2,1-c]pyridine-4-carbonitrile derivatives 115.
Mechanism supporting the formation of 117 starting from 116.
Crystal structure of 117. Reproduced with permission from Ref. [57].
Synthetic routes to 119 starting from 29.
Knoevenagel reactions performed in classical ethanol/piperidine conditions.
Synthetic route to push–pull dye 127.
Synthetic route to ninhydrin 138.
Different routes for halogenation of indane-1,3-dione 4 at the methylene position.
Fluorination reactions of indane-1,3-dione 4.
Mechanism involved in the fluorination of 4.
Mechanism supporting the coexistence of a radical and an electrophilic bromination pathway for the bromination of 4.
Synthesis of 150 using NBS as the bromination agent.
Synthetic route to 153.
Synthetic route to 154.
Synthetic routes to cyclophanes 158a and 158b.
Synthetic routes to the crown ether derivative of 1,3-indandione 159.
Synthetic route to 162.
Synthetic routes to tetracycline heterocyclic analogues.
Synthetic routes to 172.
Synthetic Routes to 177, 179, 181 and 182.
Synthetic routes to 185–192.
Synthetic route to 196.
Synthetic routes to porphyrins 199 and 200.
Synthetic routes to various (metallo)porphyrins.
Synthetic route to 208.
Mechanism involved in the synthesis of 212.
Synthetic routes to 212 and 213.
Chemical structures of the indeno-fused structures 216–224 treated below.
Synthetic route to 217b.
Mechanism involved in the synthesis of indeno-fused structures 218.
General mechanism of indeno-fused structures synthetized by MCR.
The different synthetic routes to spiroindanediones discussed in this part.
Synthesis of the ferrocenecarbocyaldehyde adduct 230.
Synthetic route to 235.
Synthetic routes to 236, 238, 240 and 242.
Synthetic route to azomethine ylide 245.
Synthetic routes to dihydro-spiro[indene-2,3′-pyrrolidines] 247.
Mechanism supporting the formation of a unique diastereoisomer.
Synthetic route to 250.
Synthesis of azomethine imine.
Synthesis of 256.
Mechanism supporting the synthesis of 256. Reproduced with permission from Ref. [254].
Synthetic route to chromeno [3,4-b]pyrrolidine 259.
Synthesis of chromeno [3,4-c]pyrrolidine 262 while using TMG as the base.
Synthesis of 259.
Synthesis of 262.
Synthetic route to a fluorinated dipolarophile 264 further used for cycloaddition reactions.
Cycloaddition reaction using TEBAB 266 as the catalyst.
Synthesis of 269.
Synthesis of 271.
Synthesis of 274.
Mechanism of formation of the coumarin-indanedione cycloadducts. Reproduced with permission from Ref. [258].
Synthesis of 277.
Mechanism involved in the cycloaddition reaction with Morita–Baylis–Hillman carbonates 275. Reproduced with permission from Ref. [259].
Synthesis of 281.
Mechanism supporting the formation of only one diastereoisomer during the Pd-catalyzed reaction.
Synthesis of 285.
Synthetic route to spirovinylcyclopropaneindanedione (VCP) 287.
Synthetic route to a five-membered spiroindanedione 289.
Cycloaddition reaction with VCP 287 and cinnamaldehyde 292.
Cycloaddition reactions with aryl and naphthyl derivatives 295 and 296.
Mechanism of cyclization determined for cycloaddition reactions occurring with nitroalkenes. Reproduced with permission from Ref. [262].
Synthesis of 299.
Synthesis of 302.
Mechanism involved in the synthesis of the oxindole-fused spiropyrazolidine. Reproduced with permission from Ref. [265].
Annulation reaction between para-quinone methide 307 and 2-vinylspiro[cyclopropane-1,2′-indene]-1′,3′-dione 289.
Synthesis of 308.
Synthesis of 310.
Mechanism proposed to support the formation of 2-arylideneindane-1,3-diones. Reproduced with permission from Ref. [268].
Synthesis of 315.
Mechanism supporting the formation of a unique diastereoisomer during the cycloaddition of azomethine ylides 314 and arylidene-indane-1,3-diones 255. Reproduced with permission from Ref. [269].
Synthesis of 317.
The two plausible mechanisms supporting the cycloaddition reaction or the epoxidation reaction. Reproduced with permission from Ref. [270].
Synthesis of 318.
Synthetic route to 320.
Cyclotrimerization reaction of 319 and 320.
Synthesis of 325.
Synthetic route to 327.
Synthetic route to 329 and 331.
Synthetic route to 329 and 334.
Synthesis of 335.
Synthesis of compounds 338 and 339.
Cobalt-catalyzed cycloaddition reactions.
Rhodium-catalyzed cycloaddition reactions.
Mechanism involved in the Co and Rh-catalyzed cyclization reaction.
Synthetic route to 346.
Synthesis of 349.
Ni-catalyzed cycloaddition reaction furnishing 352.
Base-catalyzed [4+1] cycloaddition.
Rh-catalyzed cycloaddition reactions.
[4+4] Cycloaddition of indanone containing benzo[c]oxepines providing dibenzocycloooctadiene derivatives 359, 360, 363 and 364.
Examples of asymmetric cross [10+2] cycloadditions producing 367 starting from 365 and 249.
Synthesis of 370.
Mechanism of domino Knoevenagel/Diels–Alder/Epimerization sequence providing 370.
Synthesis of 373.
Crystal structure of a product used to determine the reaction mechanism. Reproduced with permission of Duan et al. [287].
Synthesis of 376.
Synthesis of 378.
Synthesis of 380.
Domino reactions carried out with (benzo)thiazoles 382 and 383.
Domino reactions involving a Michael addition followed by a 1,3 dipolar cycloaddition of 2-arylidene-1,3-indanediones 255 and 5-aryl-1,3,4-oxathiazol-2-ones 388.
Mechanism supporting the formation of the previous compound 395. Reproduced with permission from Ref. [290].
Synthesis of 392.
Synthetic route to 395.
Mechanism of the domino reaction between ynones 397 and 2-arylidene-indane-1,3-diones 255. Reproduced with permission from Ref. [291].
Synthesis of spiro-compounds 403 by domino reaction involving a silver-based catalyst.
Mechanism of the domino reaction involving a silver-based catalyst. Reproduced with permission from Ref. [292].
Synthetic access to 404.
Synthesis of 5′-hydroxy-6′-methyl-1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione 406.
Synthesis of 408.
Mechanism of the cascade Michael addition/cycloaddition reaction between 2-arylidene-indane-1,3-diones 255 and allenoates 407. Reproduced with permission from Ref. [293].
Synthesis of 411.
Mechanism of the domino reaction between 2-arylidene-indane-1,3-diones 255 and N-alkoxyacrylamides 410 in the presence of a base. Reproduced with permission from Ref. [294].
Synthesis of 417.
Mechanism involved in the cascade double Michael addition/acetalization reactions. Reproduced with permission from Ref. [295].
Product 423 obtained in a quadruple cascade reaction.
Mechanism involved in the quadruple cascade reaction.
Mechanism involved in the synthesis of spiro-indane-1,3-diones 428.
Synthesis of 428.
Examples of compounds 437 and 438 obtained during the MRC of indane-1,3-dione 4, dimethyl but-2-ynedioate 434 and various substituted benzothiazoles 435 or 436.
Mechanism of MRC between the MRC between indane-1,3-dione 4, dimethyl but-2-ynedioate 434 and benzothiazoles 437 or 438.
Synthesis of spiro-N-fused indane-1,3-diones 441 and 442.
Synthesis of 441 and 442.
Synthesis of 445.
Synthesis of 448 and 450.
Synthesis of 452.
Mechanism involved in the MRC reaction using Fe-particles as catalysts. Reproduced with permission from Ref. [301].
Example of pH-switchable compound 454.
Various products obtained by reacting indane-1,3-dione 4 in the presence of base.
Synthetic routes to 50 and 458.
Synthetic route to 455.
Synthetic route to 457.
Synthesis of 463.
Mechanism occurring during alkene hydrofunctionnalizations of 2-arylidene-indane-1,3-diones 255 providing 463. Reproduced with permission from Ref. [304].
Synthesis of 465.
Mechanism involved in the copper-catalyzed synthesis of spiro compounds. Reproduced with permission from Ref. [305].
Synthesis of 467.
Mechanism occurring in the copper catalyzed cycloaddition reaction of 2-arylene-indane-1,3-dione 255 with various oximes 466. Reproduced with permission from Ref. [306].
The different products obtained during the reaction of 2-arylidene-indane-1,3-diones 255 and the Seyferth–Gilbert reagent 468.
Synthesis of 469.
Chemical structures of indane-1,3-dione-based push–pull dyes 470–497.
Chemical structures of dyes 498–506.
Reaction occurring with cyanide anions.
Reaction occurring with cyanide anions.
Cyanide ion detection with 509: (a) optically with the naked eye; (b) by fluorescence changes. Reproduced with permission from Wang et al. [359].
Chemical structures of 510–518.
Synthesis of 4-hydroxyindan-1,3-diones 521 studied in the 1930s by Robinson et al. and Walker et al., first indanediones known for their antiseptic activities [388].
Examples of hydroxyindanediones 522–524 with important antibacterial activities against Bacterium typhosum.
The two families of indeno [1,2-c]pyrazoles examined for their antimicrobial activities.
Synthetic routes to 3-aryl-1-heteroarylindeno [1,2-c]pyrazol-4(1H)-ones 532.
Synthesis of ethyl 4-(9-ethyl-9H-carbazol-3-yl)-2-methyl-5-oxo-4,5-dihydro-1H-indeno [1,2-b]pyridine-3-carboxylate (ECPC) 536.
Synthesis of pyrimidine-2-thiones 538 starting from indane-1,3-dione 4 along with their corresponding antibacterial and antifungal activities.
Strategy used for the synthesis of spiro[indolo-3,10′-indeno[1,2-b]quinolin]-2,4,11′-triones 540-(IVa-IVv) along with their graphical representations of the diameter of growth of inhibition (mm) against bacteria strains. Reproduced with permission from Ref. [397].
MCR leading to two different structures of indeno-heterocycles 541. Apoptosis properties were evaluated at 25 µM.
Camptothecin-inspired pentacycle-based indeno-heterocycles 544 and 545.
Synthetic routes to indenopyridine derivatives 549 examined in Ghorab’s study.
Synthetic routes to indenopyrazoles and the best candidate 553-k.
“Push–pull” effect in IND-TPA with TICT schematisation used in this study.
(A) Generation of ROS in PBS buffer. (B) Cell viability of HeLa living cells, stained with MPAT, upon irradiation with a green light for 10 min. Reproduced with permission from Ref. [419].
Chemical structure of 557 and the different advantages of this AIE dye.
CLSM images of HCC827 (A–E) and A549 (F–J) cells after incubation with 557 (5 mM) and BODIPY493/503 (100 nM) at 37 °C for 15 min. (A,F) Bright-field images. (B,G) Fluorescence image from 557 and from BODIPY493/503. (D,I) The merged images. (E,J) The intensity profile of ROI lines. Scale bar = 20 mm. Reproduced with permission of Gao M, Su H, Lin Y, Ling X, Li S, Qin A, and Zhong Tang B. Photoactivatable aggregation-induced emission probes for lipid droplets-specific live cell imaging. Reproduced with permission from Ref. [421].
I/I0 (%) of fluorescence intensity of HCC827 cells colored with 557 (5 µM) with increasing time of irradiation at 514 nm with 7% laser power. Inset: Fluorescence images of HCC827 cells with increasing time of irradiation. Reproduced with permission from Gao M, Su H, Lin Y, Ling X, Li S, Qin A, Zhong Tang B. Photoactivatable aggregation-induced emission probes for lipid droplets-specific live cell imaging. Reproduced with permission from Ref. [421].
Series of molecules 561–564 synthetized by MWAMCR.
Plausible mechanism of the above molecules in the presence of Zn2+ cations.
Synthetic route to arylindenopyrimidines 565.
Summary of the synthetic strategy developed to access compounds 577 and 584 substituted at the 8- and 9-positions.
Summary of the synthetic strategy developed to access compounds 577 and 584 substituted at the 8- and 9-positions.
Comparisons between six compounds substituted at the 8- and the 9-positions for their in vitro and in vivo activities. In vitro activity for A2a and A1 functional assays and in vivo results for mouse catalepsy at 10 mg/kg, po.
Chemical structure of JNJ-40255293 (585).
Strategy employed for the synthesis of arylindenopyridines 589 and 593 in the patents.
Synthesis of tricyclic 3,4-dihydropyrimidine derivatives 595 via Biginelli reaction along with the most promising compounds. a human TRPA1 antagonism b rat TRPA1 antagonism.
MCR for the synthesis of 222 with three examples having decent anticonvulsant activity. a, Values represent means SEM (n = 3). b, Rotarod toxicity (number of animals exhibiting toxicity/number of animals tested).
Synthetic route to dihydropyrimidine.
Close-up depiction of the lowest-energy three-dimensional (3-D) docking poses of 600 into the binding site of Torpedo californica acetylcholinesterase TcAChE. Reproduced with permission from Ref. [445].
Chemical structures of indane-2-arylhydrazinylmethylene-1,3-diones 605a–f and indol-2-aryldiazenylmethylene-3-ones 608a–m.
Chemical structures of various indane-1,3-dione derivatives 609–611 with anticoagulant properties.
The different synthetic routes to acylindane-1,3-diones 613.
New synthetic route developed by Larsen et al. to access to acylindanediones 616.
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