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Synthesis 1987; 1987(5): 474-477
DOI: 10.1055/s-1987-33431
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The Reaction of 3,4-Dihydroisoquinolines With Malonic Acid and Its Derivatives

Jeffrey C. Pelletier* , Michael P. Cava
  • *Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, U.S.A.
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Publication Date:
18 September 2002 (online)

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The reaction of various 3,4-dihydroisoquinolines with malonic acid gives the corresponding 1,2,3,4-tetrahydro-1-isoquinolineacetic acids in good yield, while the reaction with cyanoacetic acid and malonic acid half ethyl ester affords 1,2,3,4-tetrahydro-1-isoquinoline acetonitriles and 1,2,3,4-tetrahydro-1-isoquinolineacetic esters respectively. The use of other 1,3-dicarbonyls which cannot decarboxylate in this reaction affords the normal addition products.

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