Synthesis of 1,2,3,4-Tetrahydroisoquinoline-1-Carboxylic Acid Derivatives Via Ugi Reactions

Author(s): Ildiko Schuster, Anita Sztojkov-Ivanov, Laszlo Lazar, Ferenc Fulop

Journal Name: Letters in Organic Chemistry

Volume 4 , Issue 2 , 2007

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Abstract:

The three-component Ugi reactions of 3,4-dihydroisoquinolines, isocyanides and acids furnished 2- acyl-N-substituted-1,2,3,4-tetrahydroisoquinoline-1-carboxamides in moderate to good yields. Chiral, nonracemic acids induced only poor diastereoselectivities in the condensations. Hydrolysis of the Ugi carboxamides gave the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids, which due to their ready ability to undergo racemization, were obtained as racemic mixtures or with low enantiomeric excesses.

Keywords: Ugi reaction, isoquinolines, α-amino acids

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Article Details

VOLUME: 4
ISSUE: 2
Year: 2007
Page: [102 - 108]
Pages: 7
DOI: 10.2174/157017807780414226
Price: $65

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