Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 7
113
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Lewis Acid–Mediated Arylation of N-Protected Bromomethylindoles

, &
Pages 1241-1256 | Received 19 Jul 2008, Published online: 04 Mar 2009

REFERENCES

  • (a) Gastpar , R. ; Goldbrunner , M. ; Marko , D. ; Angerer , E. V. Methoxy-substituted 3-formyl-2-phenylindoles inhibit tubulin polymerization . J. Med. Chem. 1998 , 41 , 4965 – 4972 ; (b) Medarde , M. ; Ramos , A. C. ; Cabellero , E. ; Clairac , R. P.-L. D. ; Lopez , J. L. ; Gravalors , D. G. Synthesis and pharmacological activity of diarylindole derivatives. Cytotoxic agents based on combretastatins . Bio. Org. Med. Chem. Lett. 1999 , 9 , 2303 – 2308 ; (c) Liou , J.-P. ; Wu , C.-Y. ; Hsieh , H.-P. ; Chang , C.-Y. ; Chen , C.-M. ; Kuo , C.-C. ; Chang , J.-Y. 4- and 5-Aroylindoles as novel class of potent antitubulin agents . J. Med. Chem. 2007 , 50 , 4548 – 4552 .
  • (a) Beckers , T. ; Reissmann , T. ; Schmidt , M. ; Burger , A. M. ; Fiebig , H. H. ; Vanhoefer , V. ; Pongratz , H. ; Mahboobi , S. 2-Aroylindoles, a novel class of potent orally active small molecule tubulin inhibitors . Cancer Research 2002 , 62 , 3113 – 3119 . (b) Mahboobi , S. ; Pongratz , H. ; Hufsky , H. ; Hockemeyer , J. ; Frieser , M. ; Lyssenko , A. ; Paper , D. H. ; Bürgermeister , J. ; Böhmer , F.-D. ; Fiebig , H.-H. ; Burger , A. M. ; Bassner , S. ; Beckers , T. Synthetic 2-aroylindole derivatives as a new class of potent tubulin-inhibitory, antimitotic agents . J. Med. Chem. 2001 , 44 , 4535 – 4553 ; (b) Liou , J.-P. ; Chang , C.-Y. ; Kuo , F.-M. ; Chang , C.-W. ; Tseng , H.-Y. ; Wang , C.-C. ; Yang , Y.-N. ; Chang , J.-Y. ; Lee , S.-J. ; Hsieh , H.-P. Concise synthesis and structure–activity relationships of combretastatin A-4 analogues, 1-aroylindoles, and 3-aroylindoles, as novel classes of potent antitubulin agents . J. Med. Chem. 2004 , 47 , 4247 – 4257 .
  • La Regina , G. ; Edler , M. C. ; Brancale , A. ; Kandil , S. ; Coluccia , A. ; Piscitelli , F. ; Hamel , E. ; De Martino , G. ; Matesanz , R. ; DHaz , J. F. ; Scovassi , A. I. ; Prosperi , E. ; Lavecchia , A. ; Novellino , E. ; Artico , M. ; Silvestri , R. Arylthioindole inhibitors of tubulin polymerization. 3: Biological evaluation, Structure–activity relationships and molecular modeling studies. J. Med. Chem. 2007, 50, 2865–2874.
  • (a) Mohanakrishnan , A. K. ; Srinivasan , P. C. A versatile construction of the 8H-quino[4,3-b]carbazole ring system as a potential DNA binder . J. Org. Chem. 1993 , 60 , 1939 – 1946 ; (b) Mohanakrishnan , A. K. ; Ramesh , N. Stille Carbonylation of N-protected bromomethylindoles . Tetrahedron Lett. 2005 , 46 , 4577 – 4579 . (c) Balamurugan , R. ; Mohanakrishnan , A. K. Synthesis of N-protected indolaldehydes using modified Hass procedure . Tetrahedron 2007 , 63 , 11078 – 11085 . (d) Ramesh , N. ; Prakash , C. ; Sureshbabu , R. ; Dhayalan , V. ; Mohanakrishnan , A. K. Unusual dimerization of N-protected bromomethylindoles/benzyl bromide with arylmetal halides . Tetrahedron 2008 , 64 , 2071 – 2079 .
  • (a) Langle , S. ; Abarbri , M. ; Duchene , A. Selective double Suzuki cross-coupling reactions: Synthesis of unsymmetrical diaryl (or heteroaryl) methanes . Tetrahedron Lett. 2003 , 44 , 9255 – 9258 ; (b) Nobre , S. M. ; Monteiro , A. L. Synthesis of diarylmethane derivatives from Pd-catalyzed cross-coupling reactions of benzylic halides with arylboronic acids . Tetrahedron Lett. 2004 , 45 , 8225 – 8228 ; (c) Chang , C. P. ; Huang , Y. L. ; Hong , F. E. Biphasic Suzuki coupling reactions of aryl or benzyl bromides employing cobalt containing phosphine ligand coordinated palladium complex . Tetrahedron 2005 , 61 , 3835 – 3839 ; (d) Kuwano , R. ; Yokogi , M. Suzuki–Miyaura cross-coupling of benzylic carbonates with arylboronic acids . Org. lett. 2005 , 7 , 945 – 947 . (e) Crawforth , C. M. ; Burling , S. A. ; Fairlamb , I. J. S. ; Taylor , R. J. K. ; Whitwood , A. C. Bromobis(triphenylphosphine)(N-succinimide)palladium as a novel catalyst for Stille cross-coupling reactions . Chem. Commun. 2003 , 2194 – 2195 ; (f) McLaughlin , M. Suzuki–Miyaura cross-coupling of benzylic phosphates with arylboronic acids . Org. Lett. 2005 , 22 , 4875 – 4878 ; (g) Bandgar , B. P. ; Bettigeri , S. V. ; Phopase , J. Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with arylboronic acids under mild conditions . Tetrahedron Lett. 2004 , 45 , 6959 – 6962 ; (g) Kaneko , M. ; Hayashi , R. ; Cook , G. R. Intermolecular Friedel–Crafts reaction catalyzed by InCl3. . Tetrahedron Lett. 2007 , 48 , 7085 – 7087 .
  • (a) Mertins , K. ; Iovel , I. ; Kischel , J. ; Zapf , A. ; Beller , M. Transition-metal-catalyzed benzylation of arenes and heteroarenes . Angew. Chem. Int. Ed. 2005 , 44 , 238 – 242 ; (b) Iovel , I. ; Mertins , K. ; Kischel , J. ; Zapf , A. ; Beller , M. An efficient and general iron-catalyzed arylation of benzyl alcohol and benzyl carboxylates . Angew. Chem. Int. Ed. 2005 , 44 , 3913 – 3917 ; (c) Kischel , J. ; Jovel , I. ; Mertins , K. ; Zapf , A. ; Beller , M. A convenient FeCl3-catalyzed hydroarylation of styrenes . Org. Lett. 2006 , 8 , 19 – 22 ; (d) Rajeswaran , W. G. ; Srinivasan , P. C. An improved synthesis of 2-Arylmethylindoles . Indian J. Heterocycl. Chem. 1992 , 2 , 89 – 90 .
  • Kofink , C. C. ; Knochel , P. Syntheis of functionalized diarylmethanes via a copper-catalyzed cross-coupling of arylmagnesium reagents with benzylic phosphates. Org. Lett. 2006, 8, 4121–4124.
  • Arumugam , N. ; Srinivasan , P. C. A facile synthesis of 2-aroylindoles by the oxidation of 2-arylmethylindoles using Sarett reagent . Synth. Commun. 2003 , 33 , 2313 – 2320 .
  • Rajeswaran , W. G. ; Srinivasan , P. C. A convenient synthesis of 2-arylmethylindoles . Synthesis 1992 , 835 – 836 .

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.