Literature DB >> 16354068

A new entry to the synthesis of 2,3-disubstituted indoles.

Chisato Mukai1, Yukie Takahashi.   

Abstract

[reaction: see text] The Stille coupling of N-acyl-2-iodoanilines with the 1-(tributylstannyl)-1-substituted allenes affected the successive one-step formation of the 2-methyl-3-substituted indoles. Alternatively, the other type of 2-alkyl-3-substituted indoles could be synthesized in a one-pot operation, which consists of the Stille coupling reaction with the 1-(tributylstannyl)-1,3-disubstituted allenes, followed by TBAF treatment. This procedure could be applied to the synthesis of indomethacin.

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Year:  2005        PMID: 16354068     DOI: 10.1021/ol052179u

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Regioselective formation of 1,1-disubstituted allenylsilanes via cross-coupling reactions of 3-tri-n-butylstannyl-1-trimethylsilyl-1-propyne.

Authors:  David R Williams; Akshay A Shah
Journal:  Chem Commun (Camb)       Date:  2010-05-19       Impact factor: 6.222

2.  Indomethacin Analogues that Enhance Doxorubicin Cytotoxicity in Multidrug Resistant Cells without Cox Inhibitory Activity.

Authors:  Mitsuhiro Arisawa; Yayoi Kasaya; Tohru Obata; Takuma Sasaki; Mika Ito; Hiroshi Abe; Yoshihiro Ito; Akihito Yamano; Satoshi Shuto
Journal:  ACS Med Chem Lett       Date:  2011-03-17       Impact factor: 4.345

3.  Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates.

Authors:  Scott E Denmark; Andrea Ambrosi
Journal:  Synlett       Date:  2017-07-12       Impact factor: 2.454

4.  Myoglobin-Catalyzed C-H Functionalization of Unprotected Indoles.

Authors:  David A Vargas; Antonio Tinoco; Vikas Tyagi; Rudi Fasan
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-06       Impact factor: 15.336

5.  Straightforward protocol for the efficient synthesis of varied N(1)-acylated (aza)indole 2-/3-alkanoic acids and esters: optimization and scale-up.

Authors:  Andy J Liedtke; Kwangho Kim; Donald F Stec; Gary A Sulikowski; Lawrence J Marnett
Journal:  Tetrahedron       Date:  2012-12-02       Impact factor: 2.457

Review 6.  Goniomitine: an overview on the chemistry of this indole alkaloid.

Authors:  José C F Alves
Journal:  ISRN Org Chem       Date:  2013-12-23
  6 in total

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