Generic placeholder image

Mini-Reviews in Organic Chemistry

Author(s): Subrata Barick, Manvendra Kumar and Raj Kumar*

DOI: 10.2174/1570193X21666230906141749

DownloadDownload PDF Flyer Cite As
Synthetic Approaches and Reactions of 2-(Arylidene)benzo[b]thiophen- 3(2H)one-1,1-dioxides

Page: [151 - 161] Pages: 11

  • * (Excluding Mailing and Handling)

Explore Articles
About Journal
For Authors
For Editors
For Reviewers

Abstract

2-(Arylidene)benzo[b]thiophen-3(2H)one 1,1-dioxides are oxidized form of thioaurones. Various methods have been reported for their synthesis, e.g., a) condensation of benzo[b]thiophen- 3(2H)one 1,1-dioxides with aryl aldehydes under acidic or basic conditions, b) oxidation of thioaurones with hydrogen peroxide or sodium perborate tetrahydrate, c) from the catalytic reaction of iodonium ylides with (bis(trifluoroacetoxy)iodo) benzene in presence copper(II)acetoacetonate, d)by ring contraction of 1-thioflavones in the presence of ceric ammonium nitrate. The reports have shown addition reactions with p-thiocresol in the absence of any catalyst, conjugated addition product without hetero ring opening with Grignard reagent, forms corresponding oxime and hydrazone with hydroxyl amine and phenyl hydrazine, respectively, produces polycyclic compounds with enamines, shows contrasting behavior with NBS and gives addition products with organophosphorus compounds in both hydroxylic and non-hydroxylic solvents which depends on reaction medium. In the present minireview, we have discussed the various synthetic strategies and reactions of 2- (arylidene)benzo[b]thiophen-3(2H)one 1,1-dioxides, along with their reported utilities.

Keywords: 2-(Arylidene)benzo[b]thiophen-3(2H)one-1, 1-dioxides, (Z)-thioaurones, condensation, oxidation, iodonium ylides, ring contraction, enamines, grignard reagent, organophosphorus compounds, addition reaction, conjugated addition, polycyclic compounds.

[1]
Chen, H.; Liu, L.; Huang, T.; Chen, J.; Chen, T. Direct dehydrogenation for the synthesis of α, β‐unsaturated carbonyl compounds. Adv. Synth. Catal., 2020, 362(16), 3332-3346.
[http://dx.doi.org/10.1002/adsc.202000454]
[2]
Hossain, M.; Das, U.; Dimmock, J.R. Recent advances in α,β-unsaturated carbonyl compounds as mitochondrial toxins. Eur. J. Med. Chem., 2019, 183, 111687.
[http://dx.doi.org/10.1016/j.ejmech.2019.111687] [PMID: 31539776]
[3]
Amslinger, S. The tunable functionality of α,β-unsaturated carbonyl compounds enables their differential application in biological systems. ChemMedChem, 2010, 5(3), 351-356.
[http://dx.doi.org/10.1002/cmdc.200900499] [PMID: 20112330]
[4]
Bag, S.; Ghosh, S.; Tulsan, R.; Sood, A.; Zhou, W.; Schifone, C.; Foster, M.; LeVine, H., III; Török, B.; Török, M. Design, synthesis and biological activity of multifunctional α,β-unsaturated carbonyl scaffolds for Alzheimer’s disease. Bioorg. Med. Chem. Lett., 2013, 23(9), 2614-2618.
[http://dx.doi.org/10.1016/j.bmcl.2013.02.103] [PMID: 23540646]
[5]
Lee, J.I. Synthetic approaches to (Z )‐Thioaurones. Bull. Korean Chem. Soc., 2021, 42(9), 1210-1219.
[http://dx.doi.org/10.1002/bkcs.12345]
[6]
Hallgas, B.; Patonay, T.; Kiss-Szikszai, A.; Dobos, Z.; Hollósy, F.; Erős, D.; Őrfi, L.; Kéri, G.; Idei, M. Comparison of measured and calculated lipophilicity of substituted aurones and related compounds. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2004, 801(2), 229-235.
[http://dx.doi.org/10.1016/j.jchromb.2003.11.021] [PMID: 14751791]
[7]
Réamonn, L.S.S.; O’Sullivan, W.I. Configuration of 2-arylmethylene-2,3-dihydro-5-methylbenzo[b]thiophen-3-ones. J. Chem. Soc., Perkin Trans. 1, 1977, (9), 1009-1012.
[http://dx.doi.org/10.1039/P19770001009]
[8]
Lanfry, M. Thiophènes.—Sur un S. Dioxy-thionaphtène. Compt Rend., 1912, 154, 519.
[9]
Mustafa, A.; Zayed, S.M.A.D. Reactions with Mercaptans. IV. Reaction of aromatic thiols with 3(2H)-Thianaphthenone-1,1-dioxides and 2-Benzylidene-3(2H)-thianaphthenone-1-1-dioxide. J. Am. Chem. Soc., 1957, 79(13), 3500-3502.
[http://dx.doi.org/10.1021/ja01570a053]
[10]
Mustafa, A.; Sallam, M.M. Experiments with 2-Arylidene-3(2H)-thianaphthenone-1,1-dioxides. II. Reactions of p-Thiocresol and of Grignard Reagents with 2-Arylidene-3(2H)-thianaphthenone-1,1-dioxides. J. Am. Chem. Soc., 1959, 81(8), 1980-1983.
[http://dx.doi.org/10.1021/ja01517a048]
[11]
Xu, B.; Sheibani, E.; Liu, P.; Zhang, J.; Tian, H.; Vlachopoulos, N.; Boschloo, G.; Kloo, L.; Hagfeldt, A.; Sun, L. Carbazole-based hole-transport materials for efficient solid-state dye-sensitized solar cells and perovskite solar cells. Adv. Mater., 2014, 26(38), 6629-6634.
[http://dx.doi.org/10.1002/adma.201402415] [PMID: 25124337]
[12]
Leung, M.; Chang, C.C.; Wu, M.H.; Chuang, K.H.; Lee, J.H.; Shieh, S.J.; Lin, S.C.; Chiu, C.F. 6-N,N-diphenylaminobenzofuran-derived pyran containing fluorescent dyes: A new class of high-brightness red-light-emitting dopants for OLED. Org. Lett., 2006, 8(12), 2623-2626.
[http://dx.doi.org/10.1021/ol060803c] [PMID: 16737329]
[13]
Ning, Z.; Tian, H. Triarylamine: A promising core unit for efficient photovoltaic materials. Chem. Commun., 2009, (37), 5483-5495.
[http://dx.doi.org/10.1039/b908802d] [PMID: 19753339]
[14]
Bakhouch, M.; Es-Sounni, B.; Nakkabi, A.; El Yazidi, M. Thioaurones: Recent advances in synthesis, reactivity, and biological activity. Mini Rev. Org. Chem., 2021, 18(3), 313-327.
[http://dx.doi.org/10.2174/1570193X17999200719135019]
[15]
Bhagwat, A.A.; Mohbiya, D.R.; Avhad, K.C.; Sekar, N. Viscosity-active D-π-A chromophores derived from benzo[b]thiophen-3(2H)-one 1,1-dioxide (BTD): Synthesis, photophysical, and NLO properties. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2018, 203, 244-257.
[http://dx.doi.org/10.1016/j.saa.2018.05.101] [PMID: 29874635]
[16]
Sobolev, A.; Zhalubovskis, R.; Franssen, M.C.R.; Vigante, B.; Chekavichus, B.; Duburs, G.; de Groot, A. Candida rugosa lipase-catalyzed kinetic resolution of 3-(isobutyryloxy)methyl 4-[2-(Difluoromethoxy)phenyl]-2-methyl-5,5-dioxo-1,4-dihydrobenzothieno[3,2-b]pyridine-3-carboxylate. Chem. Heterocycl. Compd., 2004, 40(7), 931-937.
[http://dx.doi.org/10.1023/B:COHC.0000044578.17992.95]
[17]
Köttner, L.; Schildhauer, M.; Wiedbrauk, S.; Mayer, P.; Dube, H. Oxidized hemithioindigo photoswitches—influence of oxidation state on (Photo)physical and photochemical properties. Chemistry, 2020, 26(47), 10712-10718.
[http://dx.doi.org/10.1002/chem.202002176] [PMID: 32485011]
[18]
Andersson, M.A.; Allenmark, S.G. Asymmetric sulfoxidation catalyzed by a vanadium bromoperoxidase: Substrate requirements of the catalyst. Tetrahedron, 1998, 54(50), 15293-15304.
[http://dx.doi.org/10.1016/S0040-4020(98)00956-9]
[19]
Adam, W.; Hadjiarapoglou, L.; Nestler, B. Dimethyldioxirane epoxidation of α,β-unsaturated ketones, acids and esters. Tetrahedron Lett., 1990, 31(3), 331-334.
[http://dx.doi.org/10.1016/S0040-4039(00)94547-7]
[20]
Adam, W.; Golsch, D.; Hadjiarapoglou, L.; Lévai, A.; Nemes, C.; Patonay, T. Dioxirane oxidation of (Z)-1-thioaurones, (E)-3-arylidene-1-thiochroman-4-ones and (E)-3-arylidene-1-thioflavan-4-ones. Tetrahedron, 1994, 50(46), 13113-13120.
[http://dx.doi.org/10.1016/S0040-4020(01)89320-0]
[21]
Benferraha, N.; Hammadia, M.; Villeminc, D. Heterogeneous Catalyst BaO-KF: Dry synthesis of thioaurones as cytotoxics agents under focused microwaves irradiation. J. Chem. Pharm. Res., 2016, 8(11), 75-82.
[22]
Pradhan, T.K.; De, A. Application of directed metalation in synthesis. Part 7: Synthesis of suitably functionalised benzo[b]thiophenes as key intermediates in the synthesis of benzothienopyranones. Tetrahedron Lett., 2005, 46(9), 1493-1495.
[http://dx.doi.org/10.1016/j.tetlet.2005.01.038]
[23]
Lee, J.I. One-pot synthesis of (Z)-Thioaurones from N-Methoxy-N-methyl 2-mercaptobenzamide and arylethynyllithiums. J. Korean Chem. Soc., 2019, 63(5), 398-402.
[24]
Wadsworth, D.H.; Detty, M.R. Regiochemical control of the addition of aryl selenols and aryl thiols to the triple bond of arylpropiolates. Synthesis of seleno- and thioflavones and seleno- and thioaurones. J. Org. Chem., 1980, 45(23), 4611-4615.
[http://dx.doi.org/10.1021/jo01311a013]
[25]
Ukai, S.; Hirose, K.; Kayano, M. Synthesis and biological activity of sulfur containing derivatives of chalcone. IV. A novel method for the synthesis of thioaurones (author’s transl). Yakugaku Zasshi, 1975, 95(3), 299-303.
[http://dx.doi.org/10.1248/yakushi1947.95.3_299] [PMID: 1171180]
[26]
Nguyen, T.B.; Retailleau, P. Cooperative activating effect of tertiary amine/DMSO on elemental sulfur: Direct access to thioaurones from 2′-nitrochalcones under mild conditions. Org. Lett., 2018, 20(1), 186-189.
[http://dx.doi.org/10.1021/acs.orglett.7b03547] [PMID: 29219319]
[27]
Somogyi, L. Transformation of 1-thioflavonoids by oxidation and dehydrogenation. Synth. Commun., 1999, 29(11), 1857-1872.
[http://dx.doi.org/10.1080/00397919908086175]
[28]
Awad, S.B.; Abdul-Malik, N.F. Studies on Benzo[b]thiophen derivatives. Synthesis and reactions of 2-p-substituted Benzoylbenzo[b]thiophen-3(2H)ones. Aust. J. Chem., 1975, 28(3), 601-605.
[http://dx.doi.org/10.1071/CH9750601]
[29]
Kamila, S.; Mukherjee, C.; Pradhan, T.K.; De, A. Synthetic studies in sulfur heterocycles. One-pot synthesis of “thioaurones” and their conversion into [1] benzothieno[3,2-b]pyrans via tandem reactions. ARKIVOC, 2006, 2, 45-60.
[30]
Hadjiarapoglou, L.; Schank, K. Reactions of 2,3-dihydro-2-phenyliodonium-3-oxo-benzo[b] thiolenide-1,1-dioxide. Tetrahedron Lett., 1989, 30(48), 6673-6676.
[http://dx.doi.org/10.1016/S0040-4039(00)70647-2]
[31]
Somogyi, L. Elimination, ring-contraction, and fragmentation reactions of 1-thioflavanone 1-oxides. Cancer J. Chem., 2001, 79(7), 1159-1165.
[http://dx.doi.org/10.1139/v01-096]
[32]
Mustafa, A.; Asker, W.; Khattab, S.; El Din Sobhy, M.E.; Fleifel, A.M.; Abu-Elazayem, K. Action of grignard reagents. XVII. 1 action of organomagnesium compounds on 5-Arylidene derivatives of 3-arylrhodanines, of 3-p-Tolyl-2,4-thiazolidinedione and on 2-Arylidene-3(2H)-4,5-benzthianaphthenone-1,1-dioxides. J. Am. Chem. Soc., 1960, 82(8), 2029-2032.
[http://dx.doi.org/10.1021/ja01493a044]
[33]
Dubure, R.R.; Vigante, B.A.; Ozols, Y.Y.; Dubur, G.Y.; Rozentale, G.I. 1,4-Dihydrobenzothieno[3,2-b]pyridine-5,5-dioxides. Chem. Heterocycl. Compd., 1986, 22(11), 1267-1271.
[http://dx.doi.org/10.1007/BF00471815]
[34]
Cekavicus, B.; Vigante, B.; Rucins, M.; Birkmane, K.; Petrova, M.; Belyakov, S.; Zuka, L.; Plotniece, A.; Pajuste, K.; Gosteva, M.; Sobolev, A. Contrasting behaviour of NBS towards 1,4-dihydrobenzothieno[3,2-b]pyridine 5,5-dioxides and 4,5-dihydro-1H-indeno[1,2-b]pyridines. Tetrahedron., 2013, 69(26), 5550-5557.
[http://dx.doi.org/10.1016/j.tet.2013.04.060]
[35]
Mustafa, A.; Sidky, M.M.; Zayed, S.M.A.D.; Abdo, W.M. Organophosphorus compounds—VIII. Tetrahedron., 1968, 24(13), 4725-4731.
[http://dx.doi.org/10.1016/S0040-4020(01)98668-5]