Synthesis of furo[2,3-b]pyridin-4(7H)-ones and related quinolinone via Brønsted acid-promoted cyclisation of alkynes

Tetrahedron Letters

Volumn 50, Issue 6, 2009, Pages 614-616

  Bossharth, Emmanuel ^a   Desbordes, Philippe ^b   Monteiro, Nuno ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

^b BAYER AG   (Germany)

Author keywords

3 Alkynyl 2 pyridones; Br nsted acids; Electrophilic annulation; Furopyridinium salts; Furo 2,3 b pyridin 4 ones

Indexed keywords

ALKYNE DERIVATIVE; BRONSTED ACID; FURO[2,3 B]PYRIDIN 4(7H) ONE DERIVATIVE; FURO[2,3 B]QUINOLIN 4(9H) ONE DERIVATIVE; HALIDE; PALLADIUM; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDRATION;

EID: 57749092637     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.11.073     Document Type: Article

References (20)

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8. +: 240.1025.
9. It is worthy of note that the use of TFA in lieu of AcOH allowed the cyclisation process to take place at room temperature. However, selective cleavage of the 4-methoxy group proved problematic as decomposition of the resulting furopyridinium salt occurred at higher temperatures. Isolation of 2-pyridone 5 as the major side product indicated that competitive cleavage of the furan ring was taking place. For an application of this type of process to the synthesis of quinolin-2-one alkaloids, see: Gaston, J. L.; Grundon, M. F. J. Chem. Soc., Perkin Trans. 1 1989, 905.{A figure is presented}
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