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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 21
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Original Articles

Methylsulfonic Acid Adsorbed on Silica Gel as a Solid Acid for Dimerization of Indoles: A Convenient Synthesis of 2,3′-Bi(3H-indol)-3-one Oximes

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Pages 2926-2935 | Received 08 Oct 2012, Published online: 25 Jul 2013

REFERENCES

  • (a) Sundberg , R. J. Indoles ; Academic Press : San Diego , 1996 ; (b) Cacchi , S. ; Fabrizi , G. Synthesis and functionalization of indoles through palladium-catalyzed reactions. Chem. Rev. 2005, 105, 2873–2920 ; (c) Joucla , L. ; Djakovitch , L. Transition metal-catalysed, direct and site-selective N1-, C2-, or C3-arylation of the indole nucleus: Twenty years of improvements. Adv. Synth. Catal. 2009, 351, 673–714 ; (d) Bandini , M. ; Eichholzer , A. Catalytic functionalization of indoles in a new dimension. Angew. Chem. Int. Ed. 2009, 48, 9608–9644 ; (e) Bartoli , G. ; Bencivenni , G. ; Dalpozzo , R. Organocatalytic strategies for the asymmetric functionalization of indoles. Chem. Soc. Rev. 2010, 39, 4449–4465 .
  • Hoessel , R. ; Leclerc , S. ; Endicot , J. ; Noble , M. ; Lawrie , A. ; Tunnah , P. ; Leost , M. ; Damiens , E. ; Marie , D. ; Marko , D. ; Niederberger , E. ; Tang , W. ; Eisenbrand , G. ; Meijer , L. Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases . Nat. Cell Biol. 1999 , 1 , 60 – 67 .
  • Kritsanida , M. ; Magiatis , P. ; Skaltsounis , A. L. ; Peng , Y. Y. ; Li , P. ; Wennogle , L. P. Synthesis and antiproliferative activity of 7-azaindirubin-3′-oxime, a 7-aza isostere of the natural indirubin pharmacophore . J. Nat. Prod. 2009 , 72 , 2199 – 2202 , and references cited therein .
  • Shintani , A. ; Toume , K. ; Rifai , Y. ; Arai , M. A. ; Ishibashi , M. A bisindole alkaloid with hedgehog signal inhibitory activity from the myxomycete Perichaena chrysosperma . J. Nat. Prod. 2010 , 73 , 1711 – 1713
  • (a) Liu , J. F. ; Jiang , Z. Y. ; Wang , R. R. ; Zheng , Y. T. ; Chen , J. J. ; Zhang , X. M. ; Ma , Y. B. Isatisine A, a novel alkaloid with an unprecedented skeleton from leaves of Isatis indigotica . Org. Lett. 2007 , 9 , 4127 – 4129 ; (b) Lee , J. ; Panek , J. S. Total synthesis of (+)-isatisine A . Org. Lett. 2011 , 13 , 502 – 505 ; (c) Zheng , H. Z. ; Dong , Z. H. ; Yuin , Q. Modern Study of Traditional Chinese Medicine, Vol. 1, Xueyaun: Beijing, 1997, pp. 328–334 .
  • (a) Pezzella , A. ; Panzella , L. ; Crescenzi , O. ; Napolitano , A. ; Navaratman , S. ; Edge , R. ; Land , E. J. ; Barone , V. ; d'Ischia , M. Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: Integrated chemical, pulse radiolytic, and quantum mechanical investigation. J. Am. Chem. Soc. 2006, 128, 15490–15498; (b) Panzella , L. ; Pezzella , A. ; Napolitano , A. ; d′Ischia , M. The first 5,6-dihydroxyindole tetramer by oxidation of 5,5′,6,6′-tetrahydroxy-2,4′-biindolyl and an unexpected issue of positional reactivity en route to eumelanin-related polymers. Org. Lett. 2007, 9, 1411–1414; (c) Pezzella , A. ; Panzella , L. ; Natangelo , A. ; Arzillo , M. ; Napolitano , A. ; d'Ischia , M. 5,6-Dihydroxyindole tetramers with “anomalous” interunit bonding patterns by oxidative coupling of 5,5′,6,6′-tetrahydroxy- 2,7′-biindolyl: Emerging complexities on the way toward an improved model of eumelanin buildup. J. Org. Chem. 2007, 72, 9225–9230; (d) Gribble , G. W. ; Pelcman , B. Total syntheses of the marine sponge pigments fascaplysin and homofascaplysin B and C. J. Org. Chem. 1992, 57, 3636–3642; (e) Keller , P. A. ; Yepuri , N. R. ; Kelso , M. J. ; Mariani , M. ; Skelton , B. W. ; White , A. H. Oxidative coupling of indoles using thallium(III) trifluoroacetate. Tetrahedron 2008, 64, 7787–7795.
  • (a) Liang , Z. J. ; Zhao , J. L. ; Zhang , Y. H. Palladium-catalyzed regioselective oxidative coupling of indoles and one-pot synthesis of acetoxylated biindolyls . J. Org. Chem. 2010 , 75 , 170 – 177 ; (b) Wahlström , N. ; Slätt , J. ; Stensland , B. ; Ertan , A. ; Bergman , J. ; Janosik , T. Synthetic applications of cyanoacetylated bisindoles: Synthesis of novel cycloheptadiindoles, indolocarbazoles, and related aza analogues . J. Org. Chem. 2007 , 72 , 5886 – 5889 ; (c) Wada , Y. ; Nagasaki , H. ; Tokuda , M. ; Orito , K. Synthesis of N-protected staurosporinones . J. Org. Chem. 2007 , 72 , 2008 – 2014 ; (d) Li , Y. ; Wang , W. H. ; Yang , S. D. ; Li , B. J. ; Feng , C. ; Shi , Z J. Oxidative dimerization of N-protected and free indole derivatives toward 3,3′- biindoles via Pd-catalyzed direct C-H transformation . Chem. Commun. 2010 , 46 , 4553 – 4555 ; (e) Benincori , T. ; Piccolo , O. ; Rizzo , S. ; Sannicolò , F. 3,3′-Bis(diphenylphosphino)-1,1′-disubstituted-2,2′- biindoles: Easily accessible, electron-rich, chiral diphosphine ligands for homogeneous enantioselective hydrogenation of oxoesters . J. Org. Chem. , 2000 , 65 , 8340 – 8347 ; (f) Bergman , J. ; Koch , E. ; Pelcman , B. 2,2′-Biindolyl revisited: Synthesis and reactions . Tetrahedron 1995 , 51 , 5631 – 5642 .
  • Li , Y. X. ; Ji , K. G. ; Wang , H. X. ; Ali , S. ; Liang , Y.-M. Iodine-induced regioselective C-C and C-N bonds formation of N-protected indoles . J. Org. Chem. 2011 , 76 , 744 – 747 .
  • (a) Xu , X. H. ; Liu , G. K. ; Azuma , A. ; Tokunaga , E. ; Shibata , N. Synthesis of indole and biindolyl triflones: Trifluoromethanesulfonylation of indoles with Tf2O/TTBP (2,4,6-tri-tert- butylpyridine) system . Org. Lett. 2011 , 13 , 4854 – 4857 ; (b) Yepuri , N. R. ; Haritakul , R. ; Keller , P. A. ; Skelton , B. W. ; White , A. H. Reactions of electron-rich indoles with triflic anhydride . Tetrahedron Lett. 2009 , 50 , 2051 – 2054 .
  • (a) Buchmeiser , M. R. Polymer-supported well-defined metathesis catalysts . Chem. Rev. 2009 , 109 , 303 – 321 ; (b) Fraile , J. M. ; García , J. I. ; Mayoral , J. A. Noncovalent immobilization of enantioselective catalysts . Chem. Rev. 2009 , 109 , 360 – 417 ; (c) Benaglia , M. ; Puglisi , A. ; Cozzi , F. Polymer-supported organic catalysts . Chem. Rev. 2003 , 103 , 3401 – 3430 ; (d) Singh , M. S. ; Chowdhury , S. Recent developments in solvent-free multicomponent reactions: A perfect synergy for eco-compatible organic synthesis . RSC Adv. 2012 , 2 , 4547 – 4592 .
  • (a) Sharma , G. ; Kumar , R. ; Chakraborti , A. K. Fluoroboric acid adsorbed on silica-gel (HBF4-SiO2) as a new, highly efficient, and reusable heterogeneous catalyst for thia-Michael additionto α,β-unsaturated carbonyl compounds . Tetrahedron Lett. 2008 , 49 , 4272 – 4275 ; (b) Bandgar , B. P. ; Patil , A. V. Fluoroboric acid adsorbed on silica gel–catalyzed regioselective ring opening of epoxides with nitrogen heterocycles . Tetrahedron Lett. 2007 , 48 , 173 – 176 ; (c) Bandgar , B. P. ; Patil , A. V. ; Kamble , V. T. ; Totre , J. V. An efficient synthesis of thiiranes from oxiranes using fluoroboric acid adsorbed on silica gel (HBF4-SiO2) as a catalyst under mild conditions in the absence of solvent . J. Mol. Catal. A: Chem. 2007 , 273 , 114 – 117 ; (d) Bandgar , B. P. ; Patil , A. V. ; Chavan , O. S. Silica-supported fluoroboric acid as a novel, efficient, and reusable catalyst for the synthesis of 1,5-benzodiazepines under solvent-free conditions . J. Mol. Catal. A: Chem. 2006 , 256 , 99 – 105 ; (e) Chakraborti , A. K. ; Gulhane , R. Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines . Tetrahedron Lett. 2003 , 44 , 3521 – 3525 .
  • (a) Liu , P. N. ; Li , D. ; Wang , Q. W. ; Zhao , S. L. ; Xia , F. ; Ren , Y. J. ; Gong , X. Q. ; Chen , J. Q. Perchloric acid–catalyzed homogeneous and heterogeneous addition of β-dicarbonyl compounds to alcohols and alkenes and investigation of the mechanism. J. Org. Chem. 2010, 75, 5017–5030; (b) Shaterian , H. R. ; Yarahmadi , H. ; Ghashang , M. Silica-supported perchloric acid (HClO4-SiO2): An efficient and recyclable heterogeneous catalyst for the one-pot synthesis of amidoalkyl naphthols. Tetrahedron 2008, 64, 1263–1269; (c) Chakraborti , A. K. ; Gulhane , R. Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines. Chem. Commun. 2003, 1896–1897; (d) Shaterian , H. R. ; Shahrekipoor , F. ; Ghashang , M. Silica-supported perchloric acid (HClO4-SiO2): A highly efficient and reusable catalyst for the protection of hydroxyl groups using HMDS under mild and ambient conditions. J. Mol. Catal. A: Chem. 2007, 272, 142–151; (e) Das , B. ; Laxminarayana , K. ; Ravikanth , B. Application of heterogeneous catalysts for an efficient synthesis of β-keto enol ethers. J. Mol. Catal. A: Chem. 2007, 271, 131–133; (f) Das , B. ; Venkateswarlu , K. ; Suneel , K. ; Majhi , A. An efficient and convenient protocol for the synthesis of quinoxalines and dihydropyrazines via cyclization-oxidation processes using HClO4 · SiO2 as a heterogeneous recyclable catalyst. Tetrahedron Lett. 2007, 48, 5371–5374; (g) Khatik , G. L. ; Sharma , G. ; Kumar , R. ; Chakraborti , A. K. Scope and limitations of HClO4-SiO2 as an extremely efficient, inexpensive, and reusable catalyst for chemoselective carbon–sulfur bond formation. Tetrahedron 2007, 63, 1200–1210; (h) Ansari , M. I. ; Hussain , M. K. ; Yadav , N. ; Gupta , P. K. ; Hajela , K. Silica-supported perchloric acid–catalyzed rapid N-formylation under solvent-free conditions. Tetrahedron Lett. 2012, 53, 2063–2065.
  • (a) Liu , P. N. ; Xia , F. ; Wang , Q. W. ; Ren , Y. J. ; Chen , J. Q. Triflic acid adsorbed on silica gel as an efficient and recyclable catalyst for the addition of β-dicarbonyl compounds to alcohols and alkenes . Green Chem. 2010 , 12 , 1049 – 1055 ; (b) Pârvulescu , A. N. ; Gagea , B. C. ; Pârvulescu , V. I. ; Vos , D. D. ; Jacobs , P. A. Acylation of 2-methoxynaphthalene with acetic anhydride over silica-embedded triflate catalysts . Appl. Catal. A 2006 , 306 , 159 – 164 ; (c) Pârvulescu , A. N. ; Gagea , B. C. ; Poncelet , G. ; Pârvulescu , V. I. Acylation of alcohols and activated aromatic compounds on silica embedded-triflate catalysts . Appl. Catal. A 2006 , 301 , 133 – 137 ; (d) Gagea , B. C. ; Pârvulescu , A. N. ; Poncelet , G. ; Pârvulescu , V. I. Alkylation of hydroquinone with tert-butanol over silica-immobilized triflate derivatives . Catal. Lett. 2005 , 105 , 219 – 222 ; (e) Gagea , B. C. ; Pârvulescu , A. N. ; Pârvulescu , V. I. ; Auroux , A. ; Grange , P. ; Poncelet , G. Alkylation of phenols and naphthols on silica-immobilized triflate derivatives . Catal. Lett. 2003 , 91 , 141 – 144 .
  • Sharghi , H. ; Asemani , O. Methanesulfonic acid/SiO2 as an efficient combination for the synthesis of 2-substituted aromatic and aliphatic benzothiazoles from carboxylic acids . Synth. Commun. 2009 , 39 , 860 – 867 .
  • Qin , W. B. ; Chang , Q. ; Bao , Y. H. ; Wang , N. ; Chen , Z. W. ; Liu , L. X. Metal-free catalyzed oxidative trimerization of indoles by using TEMPO in air: A novel entry to 3-(1H-indol-3-yl)-3,3′-biindolin-2-ones . Org. Biomol. Chem. 2012 , 10 , 8814 – 8821 .
  • Yong , T. E. ; Auld , D. S. Biindolyls. II. 2-(3-Indolyl)-3H-pseudoindol-3-ones from the condensation of isatin α -chlorides with indoles . J. Org. Chem. 1963 , 28 , 418 – 421 .
  • Astolfi , P. ; Panagiotaki , M. ; Rizzoli , C. ; Greci , L. Reactions of indole with nitrogen dioxide and nitrous acid in an aprotic solvent . Org. Biomol. Chem. 2006 , 4 , 3282 – 3290 .

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