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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 4, Issue 2, 2007

Page: [102 - 108] Pages: 7

DOI: 10.2174/157017807780414226

Price: $65

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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