2-Trifluoroacetyl aminoindoles as useful intermediates for the preparation of 2-acylamino indoles

A three-step method was developed to convert N-1 unprotected 3-substituted indoles to 3-substituted 2-acylaminoindoles. Established indole chlorination chemistry was employed to generate stable 2-trifluoroacetylamino indoles, which were subsequently deprotected and selectively acylated.

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Bibliographic Details
Published inTetrahedron letters Vol. 52; no. 12; pp. 1292 - 1295
Main Authors Mangette, John E., Chen, Xuemei, Krishnamoorthy, Ravi, Samuel Vellekoop, A., Csakai, Adam J., Camara, Fatoumata, Paquette, William D., Wang, Hong-Jun, Takahashi, Hidenori, Fleck, Roman, Roth, Gregory P.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.03.2011
Elsevier
Subjects
2-Aminoindole
2-Aminoindole acylation
Acylaminoindole
Chemistry
Chemistry, Organic
Chlorination
Chloroindolenine
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indoles
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Tetrahedrons
2-Aminoindole acylation
Acylaminoindole
2-Aminoindole
Chloroindolenine
TRYPTOPHAN
REDUCTIVE ACYLATION
3-NITROINDOLES
DERIVATIVES
CYCLIZATION
Chlorination
Nitrogen heterocycle
Deprotection
Selectivity
Indole derivatives
Chemical synthesis
Acylation
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Summary:A three-step method was developed to convert N-1 unprotected 3-substituted indoles to 3-substituted 2-acylaminoindoles. Established indole chlorination chemistry was employed to generate stable 2-trifluoroacetylamino indoles, which were subsequently deprotected and selectively acylated.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.01.051