Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 10
188
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

PTC‐Promoted Japp–Klingmann Reaction for the Synthesis of Indole Derivatives

, , &
Pages 1359-1368 | Received 30 Nov 2004, Published online: 16 Aug 2006

References

  • Bartoszyk , G. D. , Hegenbart , R. and Ziegler , H. 1997 . EMD 68843, a serotonin reuptake inhibitor with selective presynaptic 5‐HT receptor agonistic properties . Eur. J. Pharmacol. , 322 ( 2 ) : 147 – 153 .
  • Heinrich , T. and Bottcher , H. 2004 . A new synthesis of indole 5‐carboxylic acids and 6‐hydroxy‐indole‐5‐carboxylic acids in the preparation of an o‐hydroxylated metabolite of vilazodone . Bioorg. Med. Chem. Lett. , 14 ( 10 ) : 2681 – 2684 .
  • Gribble , G. W. 2000 . Recent developments in indole ring synthesis‐methodology and applications . J. Chem. Soc., Perkin Trans 1 , : 1045 – 1075 .
  • Gilchrist , T. L. 2001 . Synthesis of aromatic heterocycles . J. Chem. Soc., Perkin Trans 1 , : 2491 – 2515 .
  • Ihara , M. and Fukumoto , K. 1995 . Recent progress in the chemistry of non‐monoterpenoid indole alkaloids . Nat. Prod. Rep. , 12 ( 3 ) : 277 – 301 .
  • Maddirala , S. J. , Gokak , V. S. , Rajur , S. B. and Basanagoudar , L. D. 2003 . Fischer indolisation of 2,6‐dialkyl and 2,4,6‐trialkylphenylhydrazones of diketones and ketoesters . Tetrahedron Lett. , 44 ( 30 ) : 5665 – 5668 .
  • Suvorov , N. N. , Gordeev , E. N. and Vasin , M. V. 1974 . Indole derivatives. CI. Synthesis and biological activity of some tryptamines . Khimiya Geterotsiklicheskikh Soedinenii. , 11 : 1496 – 1501 .
  • Suvorov , N. N. , Vinograd , L. Kh. , Turchin , K. F. , Il'ina , G. N. , Vigdorchik , M. M. and Filipenko , T. Ya. 1984 . Indole derivatives. 125. Synthesis of disubstituted tryptamines . Khim. Geterotsikl. Soed. , 8 : 1093 – 1100 .
  • Franco , F. , Luigi , D. B. and Ermanno , D. The total synthesis of melatonin as a drug for therapy of AIDS. . Eur. Pat. Appl. EP 330625 . Aug 30, 1989; .
  • Prabhakar , C. , Kumar , V. N. , Reddy , R. M. , Sarma , R. M. and Reddy , O. G. 1999 . Process research and development of melatonin . Org. Process Res. Dev. , 3 ( 3 ) : 155 – 160 .
  • Salm , R. F. , Zinsmeister , H. D. and Eicher , T. 1998 . Nitrogen‐containing compounds from the moss fontinanis aquamosaf . Phytochemistry , 49 ( 3 ) : 887 – 892 .
  • Sun , H. , Weng , Z. and Owen , T. Y. 1982 . Tumor chemotherapy XXXXIII. Syntheses of some nitrotryptophans and their related indole acetic acids and tryptamines . Yaoxue Xuebao , 17 ( 4 ) : 275 – 281 .
  • Ohshima , T. , Shibuguchi , T. , Fukuta , Y. and Shibasaki , M. 2004 . Catalytic asymmetric phase‐transfer reactions using tartrate‐derived asymmetric two‐center organocatalysts . Tetrahedron , 60 ( 35 ) : 7743 – 7754 .
  • Yadav , G. D. and Bisht , P. M. 2004 . Novelties of microwave assisted liquid–liquid phase transfer catalysis in enhancement of rates and selectivities in alkylation of phenols under mild conditions . Catal Commun. , 5 ( 5 ) : 259 – 263 .
  • Yadav , G. D. and Subramanian , S. 2004 . Novelties of solid–liquid phase transfer catalyzed synthesis of o‐nitrodiphenyl ether . J. Mol. Catal. A: Chem. , 209 ( 1 ) : 75 – 82 .
  • Boutevin , B. , Boileau , S. , Pietrasanta , Y. and Lantz , A. Manufacture of fluorinated olefins. Fr. . Demande 2566401 . Dec. 27,1985 .
  • Winter , R. and Gard , G. L. 1990 . The synthesis of SFs‐epoxides . J. Fluorine Chem. , 50 ( 1 ) : 141 – 149 .
  • Ikeda , M. , Miura , M. and Aoshima , A. Fluoroepoxides. . Eur. Pat. Appl. EP 100488 . Feb. 15,1984 .
  • Fex , H. J. , Kristensson , S. K. and Stamvik , A. R. Carbamoylation of phenolic hydroxy groups to manufacture phenolic N‐disubstituted carbamate esters and ion‐pair solutions used in this reaction . Ger. Offen. 2629657 . Jan 27, 1977 .
  • Reddy , C. V. , Mahesh , M. , Raju , P. V. K. and Reddy , V. N. 2002 . Syn. Commun . 32 ( 18 ) : 2797 – 2802 .
  • Koch , M. V. and Magni , A. Serine derivatives . US 4501919 . Feb. 26, 1985 .
  • Misaki , S. 1985 . Conversion of methoxyperfluoroisobutene to α‐methylhexafluoroisobutyric acid fluoride by a phase transfer catalyst . J. Fluorine Chem. , 29 ( 4 ) : 471 – 474 .
  • He , W. , Li , X. , Zhang , B. and Li , Z. J. 2000 . Synthesis of melatonin—a new sleeping drug . Journal of the Fourth Military University , 21 ( 18 ) : 949 – 951 .
  • Bretherick , L. , Gaimster , K. and Wragg , W. R. 1961 . A convenient alternative synthesis of 5‐hydroxytryptamine . J. Chem. Soc. , : 2919 – 2922 .
  • Ishii , H. , Murakami , Y. , Hosoya , K. , Takeda , H. , Suzuki , Y. and Ikeda , N. 1973 . Fisher indolization and its related compounds, V. Indolization of ethylpyruvate 2‐methoxyphenylhydrazone and its N‐methyl derivative with protic acids . Chem. Pharm. Bull. , 21 : 1481 – 1494 .
  • Ishii , H. , Murakami , Y. , Furuse , T. , Hosoya , K. and Ikeda , N. 1973 . Fisher indolization and its related compounds, VI. Effect of reagents and substituent of the ortho‐substituted phenylhydrazone on abnormal Fisher indolization . Chem. Pharm. Bull. , 21 : 1495 – 1505 .

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.