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Synthesis 1987; 1987(2): 142-146
DOI: 10.1055/s-1987-27864
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A New Route to [g]-Fused 5-Methyl-1-functionalized Isoquinolines

Emile Bisagni* , Marilys Rautureau
  • *UA40533 CNRS, Laboratoire do Synthèse Organique, lnstitut Curie, Section de Biologie, Centre universitaire, Bâtiments 110-112, F-91405 Orsay, France
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Publication Date:
12 September 2002 (online)

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2-(3-Lithio-2-methoxy-4-pyridyl)-4,4-dimethyl-2-oxazoline (8) was condensed with aromatic aldehydes. Subsequent hydrolysis gave the corresponding lactones 10. Reduction by ammoniacal zinc or calalytic hydrogenation of these compounds over palladium yielded 3-arylmethyl-2-pyridone-4-carboxylic acids 11 which were transformed into 3-arylmethy1-4-acetyl-2-pyridones 12 by methyllithium. Acidic ring closure then easily led to (g)-fused 5-methyl-2H-isoquinoline-1-ones via a convergent pathway. This method is more rapid and convenient than former procedures reported for the synthesis of (g)-fused 5-methyl-1-functonalized isoquinolines.

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