Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 2
177
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

First Evidence of 1,3-Bis-indolylallenes: Generation by a Sequential Double Nucleophilic Process from Ynones

, , , , &
Pages 253-261 | Received 22 Jul 2014, Published online: 26 Nov 2014

REFERENCES

  • Gribble , G. W. ; Maes , B. U. W. , Ed. Heterocyclic Scaffolds II: Reactions and Applications of Indoles ; Topics in Heterocyclic Chemistry, 26 ; Springer : Berlin , 2010 .
  • Humphrey , G. R. ; Kuethe , J. T. Practical methodologies for the synthesis of indoles . Chem Rev. 2006 , 106 , 2875 – 2911 .
  • (a) Bandini , M. ; Eichholzer , A. Catalytic functionalization of indoles in a new dimension . Angew. Chem. Int. Ed. 2009 , 48 , 9608 – 9644 ; (b) Bartoli , G. ; Bencivenni , G. ; Dalpozzo , R. Organocatalytic strategies for the asymmetric functionalization of indoles . Chem. Soc. Rev. 2010 , 39 , 4449 – 4465 ; (c) Baglai , I. ; Maraval , V. ; Duhayon , C. ; Chauvin , R. 1-Ethyl-2-phenyl-3-[2-(trimethylsilyl)-ethynyl]-1H-indole . Acta Cryst. E 2013 , E69 , o921 – o922 .
  • Arai , T. ; Yamamoto , Y. ; Awata , A. ; Kamiya , K. ; Ishibashi , M. ; Arai , M. A. Catalytic asymmetric synthesis of mixed 3,3′-bisindoles and their evaluation as wnt signaling inhibitors . Angew. Chem. Int. Ed. 2013 , 52 , 2486 – 2490 .
  • Shiri , M. ; Zolfigol , M. A. ; Kruger , H. G. ; Tanbakouchian , Z. Bis- and trisindolylmethanes (BIMs and TIMs) . Z. Chem. Rev. 2010 , 110 , 2250 – 2293 .
  • See, for example, (a) Miki , Y. ; Aoki , Y. ; Miyatake , H. ; Minematsu , T. ; Hibino , H. Synthesis of caulersin and its isomers by reaction of indole-2,3-dicarboxylic anhydrides with methyl indoleacetates. Tetrahedron Lett. 2006, 47, 5215–5218 (b) Guchhait , S. K. ; Kashyap , M. ; Kamble , H. ZrCl4-mediated regio- and chemo-selective Friedel–Crafts acylation of indole. J. Org. Chem. 2011, 76, 4753–4758.
  • (a) Yu , H. ; Yu , Z. Gold(III) complexes containing N-heterocyclic carbine ligands: Thiol “switch-on” fluorescent probes and anti-cancer agents . Angew. Chem. Int. Ed. 2009 , 48 , 2929 – 2933 ; (b) Mandal , M. ; Kumar , D. ; Roy , R. ; Sen , R. ; Das , P. ; Chatterjee , M. ; Jaisankar , P. Regioselective one-pot synthesis of 3,3′-diindolylethylene derivatives and study of their cytotoxic activity . Bioorg. Med. Chem. Lett. 2011 , 21 , 3084 – 3087 .
  • (a) Rosillo , M. ; Domínguez , G. ; Casarrubios , L. ; Amador , U. ; Pérez-Castells , J. Tandem enyne metathesis–Diels–Alder reaction for construction of natural product frameworks . J. Org. Chem. 2004 , 69 , 2084 – 2093 ; (b) Rajakumar , P. ; Gayatri Swaroop , M. ; Jayavelu , S. ; Murugesan , K. Synthesis, complexation studies, and biological applications of some novel stilbenophanes, indolophanes, and bisindolostilbenophanes via McMurry coupling . Tetrahedron 2006 , 62 , 12041 – 12050 ; (c) Fu , L. ; Gribble , G. W. Total synthesis of lycogarubin C utilizing the Kornfeld–Boger ring contraction . Tetrahedron Lett. 2010 , 51 , 537 – 539 .
  • (a) Komander , D. ; Kular , G. S. ; Schüttelkopf , A. W. ; Deak , M. ; Prakash , K. R. C. ; Bain , J. ; Elliott , M. ; Garrido-Franco , M. ; Kozikowski , A. P. ; Alessi , D. R. ; van Aalten , D. M. F. Interactions of LY333531 and other bisindolyl maleimide inhibitors with PDK1 . Structure 2004 , 12 , 215 – 226 (b) Poot , A. J. ; van Ameijde , J. ; Slijper , M. ; van den Berg , A. ; Hilhorst , R. ; Ruijtenbeek , R. ; Rijkers , D. T. S. ; Liskamp , R. M. J. Development of selective bisubstrate-based inhibitors against protein kinase C (PKC) isozymes by using dynamic peptide microarrays . Chem. Bio. Chem 2009 , 10 , 2042 – 2051 ; (c) van Wandelen , L. T. M. ; van Ameijde , J. ; Mady , A. S. A. ; Wammes , A. E. M. ; Bode , A. ; Poot , A. J. ; Ruijtenbeek , R. ; Liskamp , R. M. J. Directed modulation of protein kinase C isozyme selectivity with bisubstrate-based inhibitors . Chem. Med. Chem 2012 , 7 , 2113 – 2121 .
  • The 5-methoxy-indole unit occurs in many biologically active compounds, and the properties of the synthesized bis-(5-methoxyindolyl) derivatives could also deserve particular attention: (a) Liou , J.-P. ; Wu , Z.-Y. ; Kuo , C.-C. ; Chang , C.-Y. ; Lu , P.-Y. ; Chen , C.-M. ; Hsieh , H.-P. ; Chang , J.-Y. Discovery of 4-amino and 4-hydroxy-1-aroylindoles as potent tubulin polymerization inhibitors . J. Med. Chem. 2008 , 51 , 4351 – 4355 ; (b) Hung , A. W. ; Silvestre , H. L. ; Wen , S. ; Ciulli , A. ; Blundell , T. L. ; Abell , C. Application of fragment growing and fragment linking to the discovery of inhibitors of Mycobacterium tuberculosis panthothenate synthetase . Angew. Chem. Int. Ed. 2009 , 48 , 8452 – 8456 .
  • Pathak , R. ; Nhlapo , J. M. ; Govender , S. ; Michael , J. P. ; van Otterlo , W. A. L. ; de Koning , C. B. A. Concise synthesis of novel naphtha[a]carbazoles and benzo[c]carbazoles . Tetrahedron 2006 , 62 , 2820 – 2830 . Note that the indole derivative 1a is not very stable and has to be prepared just before use in order to avoid degradation .
  • Suzuki , R. ; Tsukuda , H. ; Watanabe , N. ; Kuwatani , Y. ; Ueda , I. Synthesis, structure, and properties of 3,9,15-tri- and 3,6,9,12,15,18-hexasubstituted dodecadehydro[18]annulenes (C18H3R3 and C18R6) with D6h-symmetry . Tetrahedron 1998 , 54 , 2477 – 2496 .
  • An , Y.-Z. ; Rubin , Y. ; Schaller , C. ; McElvany , S. W. Synthesis and characterization of diethynylmethanobuckminsterfullerene, a building block for macrocyclic and polymeric carbon allotropes . J. Org. Chem. 1994 , 59 , 2927 – 2929 .
  • Shiri , M. Indoles in multicomponent processes (MPCs) . Chem. Rev. 2012 , 112 , 3508 – 3549 .
  • Kabalka , G. W. ; Yao , M.-L. ; Borella , S. ; Goins , L. K. Iron trichloride–mediated allylation of lithium alkoxides through an unusual carbon-oxygen bond cleavage . Organometallics 2007 , 26 , 4112 – 4114 .
  • Krause , N. ; Hoffmann-Röder , A. Synthesis of allenes with organometallic reagents . Tetrahedron 2004 , 60 , 11671 – 11694 .
  • It noteworthy that the second addition of 1b is very fast: indeed, the mono-adduct a priori expected from the hydrolysis of 8 could not be isolated, nor even detected, even from reactions performed with only one equivalent of 1b and quenched at low temperature .
  • (a) Saccavini , C. ; Tedeschi , C. ; Maurette , L. ; Sui-Seng , C. ; Zou , C. ; Soleilhavoup , M. ; Vendier , L. ; Chauvin , R. Functional [6]pericyclynes: Synthesis through [14 + 4] and [8 + 10] cyclization strategies. Chem. Eur. J. 2007, 13, 4895–4913; (b) Leroyer , L. ; Zou , C. ; Maraval , V. ; Chauvin , R. Synthesis and stereochemical resolution of a [6]pericyclynedione: Versatile access to pericyclynediol precursors of carbo-benzenes. C. R. Chimie 2009, 12, 421–429.
  • Baglai , I. ; Maraval , V. ; Bijani , C. ; Saffon-Merceron , N. ; Voitenko , Z. ; Volovenko , Y. M. ; Chauvin , R. Enhanced π-frustration in carbo-benzenic chromophores . Chem. Commun. 2013 , 49 , 8374 – 8376 .
  • For references on carbo-benzenes, see, for example, (a) Chauvin , R. “Carbomers,” I: A general concept of expanded molecules . Tetrahedron Lett. 1995 , 36 , 397 – 400 ; (b) Maraval , V. ; Chauvin , R. From macrocyclic oligo-acetylenes to aromatic ring carbo-mers . Chem. Rev. 2006 , 106 , 5317 – 343 ; (c) Rives , A. ; Baglai , I. ; Malytskyi , V. ; Maraval , V. ; Saffon-Merceron , N. ; Voitenko , Z. ; Chauvin , R. Highly π electron-rich macro-aromatics: Bis(p-aminophenyl)-carbo-benzenes and their DBA acyclic references . Chem. Commun. 2012 , 48 , 8763 – 8765 .
  • Palatinus , L. ; Chapuis , G. SUPERFLIP: A computer program for the solution of crystal structures by charge flipping in arbitrary dimensions . J. Appl. Cryst. 2007 , 40 , 786 – 790 .
  • Betteridge , P. W. ; Carruthers , J. R. ; Cooper , R. I. ; Prout , K. ; Watkin , D. J. CRYSTALS version 12: Software for guided crystal structure analysis . J. Appl. Cryst. 2003 , 36 , 1487 .
  • International Tables for X-ray Crystallography, vol. IV; Kynoch Press: Birmingham, UK , 1974 .
  • Blessing , R. H. An empirical correction for absorption anisotropy . Acta Cryst. 1995 , A51 , 33 – 38 .
  • Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.