A Novel One-Pot Synthesis of Substituted Quinolines

A synthesis of quinoline derivatives is described via reaction between ethyl bromopyruvate (=ethyl 3‐bromo‐2‐oxopropanoate), acetylenedicarboxylate, and isatin (=1H‐indole‐2,3‐dione) in the presence of NaH as a base. Also, these reactions were performed without ethyl bromopyruvate. The reaction in t...

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Bibliographic Details
Published in:Helvetica chimica acta 2010-05, Vol.93 (5), p.946-950
Main Authors: Sabbaghan, Maryam, Yavari, Issa, Hossaini, Zinatossadat, Souri, Sanaz
Format: Article
Language:English
Subjects:
1H-Indole-2
1H‐Indole‐2,3‐dione
3-dione
Acetylenedicarboxylates
ethyl 3-bromo-2-oxo
ethyl bromo
Isatin
Propanoate
Propanoate, ethyl 3‐bromo‐2‐oxo
Pyruvate
Pyruvate, ethyl bromo
Quinolines
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Summary:A synthesis of quinoline derivatives is described via reaction between ethyl bromopyruvate (=ethyl 3‐bromo‐2‐oxopropanoate), acetylenedicarboxylate, and isatin (=1H‐indole‐2,3‐dione) in the presence of NaH as a base. Also, these reactions were performed without ethyl bromopyruvate. The reaction in the presence of ethyl bromopyruvate provides regioselectively a quinoline with the ethyl ester group in 4‐position. In the absence of ethyl bromopyruvate, the reaction leads to functionalized quinolines with the same ester groups in 2‐, 3‐, and 4‐positions.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200900304