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

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

Volume: 4 Issue: 2

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

Affiliation:

Keywords: Ugi reaction, isoquinolines, α-amino acids

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.

Cite this article as:

Schuster Ildiko, Sztojkov-Ivanov Anita, Lazar Laszlo and Fulop Ferenc, Synthesis of 1,2,3,4-Tetrahydroisoquinoline-1-Carboxylic Acid Derivatives Via Ugi Reactions, Letters in Organic Chemistry 2007; 4 (2) . https://dx.doi.org/10.2174/157017807780414226