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Diastereoselective Synthesis of (–)-6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid via Morpholinone Derivatives.

Authors :
Chrzanowska, Maria
Grajewska, Agnieszka
Rozwadowska, Maria D.
Source :
Molecules. Apr2023, Vol. 28 Issue 7, p3200. 14p.
Publication Year :
2023

Abstract

A simple and convenient synthesis of (–)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid is described, applying a combination of two synthetic methods: the Petasis reaction and Pomeranz–Fritsch–Bobbitt cyclization. The diastereomeric morpholinone derivative N-(2,2-diethoxyethyl)-3-(3,4-dimethoxyphenyl)-5-phenyl-1,4-oxazin-2-one formed in the Petasis reaction was further transformed into 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid via Pomeranz–Fritsch–Bobbitt cyclization, a classical method of synthesis leading to the tetrahydroisoquinoline core. We review important examples of applications of the Pomeranz–Fritsch process and its modifications in the synthesis of chiral tetrahydroisoquinoline derivatives that have been published in the past two decades. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14203049
Volume :
28
Issue :
7
Database :
Academic Search Index
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
163042186
Full Text :
https://doi.org/10.3390/molecules28073200