Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 24
433
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of N‐Protected/Free Indole‐7‐Carboxaldehyde

, , , &
Pages 4343-4352 | Received 15 May 2007, Published online: 14 Dec 2007

References

  • Sundberg , R. J. 1970 . The Chemistry of Indoles New York : Academic Press .
  • Eenkhoom , J. A. , Desilva , O. S. and Snieckus , V. J. 1970 . Synthesis of 1‐(2‐indolyl)‐2‐arylethylene derivatives . J. Chem. Soc., Chem. Commun. , : 1095 – 1096 .
  • Sundberg , R. J. and Russel , H. F. 1973 . Syntheses with N‐protected 2‐lithioindoles . J. Org. Chem. , 38 : 3324 – 3330 .
  • Katritzky , A. R. and Akutagawa , K. 1985 . Carbon dioxide: a reagent for the protection of nucleophilic centres and the simultaneous activation of alternative locations to electrophilic attack, part I: a new synthetic method for the 2‐substitution of 1‐unsubstituted indoles . Tetrahedron Lett. , 26 : 5935 – 5938 .
  • Katritzky , A. R. and Akutagawa , K. 1986 . Carbon dioxide: a reagent for simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack, V: activation of the 2‐alkyl group of a 2‐alkylindole toward proton loss and subsequent electrophilic substitution . J. Am. Chem. Soc. , 108 : 6808 – 6809 .
  • Inagaki , S. , Naruse , Y. and Ito , Y. 1991 . Highly regioselective functionalization of 2,3‐dialkyl substituents on indoles . J. Org. Chem. , 56 : 2256 – 2258 .
  • Gribble , G. W. 2000 . Recent developments in indole ring synthesis—Methodology and applications . J. Chem. Soc., Perkin Trans. 1 , : 1045 – 1107 .
  • Moyer , M. P. , Shiurba , J. F. and Rapoport , H. 1986 . Metal–halogen exchange of bromoindoles: a route to substituted indoles . J. Org. Chem. , 51 : 5106 – 5110 .
  • Bartoli , G. , Palmier , G. , Bosco , M. and Dalpozzo , R. 1989 . The reaction of vinyl Grignard reagents with 2‐substituted nitroarenes: a new approach to the synthesis of 7‐substituted indoles . Tetrahedron Lett. , 30 : 2129 – 2132 .
  • Dobson , D. R. , Gilmore , J. and Long , D. A. 1992 . Synthesis of 7‐formylindole using the Bartoli indole methodology . Synlett , : 79 – 80 .
  • Dobbs , A. P. , Voyle , M. and Whittall , N. 1999 . Synthesis of novel indole derivatives: variations in the Bartoli reaction . Synlett , : 1594 – 1596 .
  • Pirrung , M. C. , Wedel , M. and Zhao , Y. 2002 . 7‐Alkyl indole synthesis via a convenient formation/alkylation of lithionitrobenzenes and an improved Bartoli reaction . Synlett , : 143 – 145 .
  • Kolis , S. P. , Clayton , M. T. , Grutsch , J. L. and Faul , M. M. 2003 . Synthesis of 7‐cyano‐ and 7‐acetamido‐indoles via cyanocarbonation/hydrogenation of 7‐formyl indole . Tetrahedron Lett. , 44 : 5707 – 5710 .
  • Hartung , C. G. , Fecher , A. , Chapell , B. and Snieckus , V. 2003 . Directed orthometalation approach to C‐7‐substituted indoles: Suzuki–Miyaura cross‐coupling and the synthesis of pyrrolophenanthridone alkaloids . Org. Lett. , 5 : 1899 – 1902 .
  • Ishiyama , K. and Yamada , Y. 2005 . Convenient synthesis of 7‐hydroxyindole . Tetrahedron Lett. , 46 : 1021 – 1022 .
  • Gribble , G. W. , Saulnier , M. G. , Sibi , M. P. and Obaza‐Nutaitis , J. A. 1984 . Synthesis and Diels–Alder reactions of 1,3‐dimethyl‐4‐(phenylsulfonyl)‐4H‐furo[3,4‐b]indole. a new annulation strategy for the construction of ellipticine and isoellipticine . J. Org. Chem. , 49 : 4518 – 4523 .
  • Mohanakrishnan , A. K. and Srinivasan , P. C. 1995 . A versatile construction of the 8H‐quino[4,3‐b]carbazole ring system as a potential DNA binder . J. Org. Chem. , 60 : 1939 – 1946 .
  • Mohanakrishnan , A. K. and Srinivasan , P. C. 1995 . Synthesis of 3‐aryl‐5H‐pyrido[4,3‐b]indoles . Synth. Commun. , 25 : 2415 – 2424 .
  • Mohanakrishnan , A. K. and Srinivasan , P. C. 1996 . Synthesis of 4‐substituted‐1,2,3,4‐tetrahydro‐β‐carbolines via intramolecular radical cyclisation and Heck reaction . Tetrahedron Lett. , 37 : 2659 – 2662 .
  • Batcho , A. D. and Leimgruber , W. 1990 . Indoles from 2‐methylnitrobenzenes by condensation with formamide acetals followed by reduction: 4‐benzyloxyindole . Org. Synth. Coll. , VII : 34
  • Mohanakrishnan , A. K. , Balamurugan , R. and Ramesh , N. 2005 . A facile preparation of N‐protected indolaldehydes using a modified Hass procedure . Tetrahedron Lett. , 46 : 8189 – 8193 .
  • Mehta , G. and Panda , G. 1997 . A new synthesis of corannulene . Tetrahedron Lett. , 38 : 2145 – 2148 .
  • Pindur , U. , Kim , Y.‐ S. and Mehrabani , F. 1999 . Advances in indolo[2,3‐a]carbazole chemistry: design and synthesis of protein kinase C and topoisomerase I inhibitors . Curr. Med. Chem. , 6 : 29 – 70 .
  • Mantos , E. K. and Clardy , J. 1993 . The synthesis of dithyreanitrile . Tetrahedron Lett. , 34 : 1085 – 1086 .
  • Warabi , K. , Matsunaga , S. , van Soest , R. W. M. and Fusetani , N. 2003 . Dictyodendrins A–E, the first telomerase‐inhibitory marine natural products from the sponge Dictyodendrilla verongiformis . J. Org. Chem. , 68 : 2765 – 2770 .

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.