Synthesis of new 4-aza-indoles via acyl azides

We hereby report the preparation of new azaindole derivatives starting from 2-(2-ethoxy-2-oxoethyl)nicotinic acid. Conversion of a half ester into acyl azide followed by Curtius rearrangement gave the corresponding isocyanate. Trapping of the isocyanate with different nucleophiles produced urea and...

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Bibliographic Details
Published in:Tetrahedron 2015-01, Vol.71 (2), p.252-258
Main Authors: Doğan, Sengul Dilem, Demirpolat, Eren, Yerer Aycan, Mükerrem Betül, Balci, Metin
Format: Article
Language:English
Subjects:
Acyl azide
Azaindole
Azaoxindole
Conversion
Curtius rearrangement
Cytotoxic activity
Derivatives
Esters
Isocyanates
Nucleophiles
Tetrahedrons
Ureas
Urethanes
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Summary:We hereby report the preparation of new azaindole derivatives starting from 2-(2-ethoxy-2-oxoethyl)nicotinic acid. Conversion of a half ester into acyl azide followed by Curtius rearrangement gave the corresponding isocyanate. Trapping of the isocyanate with different nucleophiles produced urea and urethane derivatives. Intramolecular cyclization reactions gave the target compounds. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.11.057