Application of the Cleavable Isocyanide in Efficient Approach to Pyroglutamic Acid Analogues with Potential Biological Activity

Two efficient procedures have been developed for the synthesis of pyroglutamic acid analogues 28 , 29 , and 34 . According to the first method the Ugi (4C3C) reaction is followed by a post-transformation reaction, and the second method involves the Michael addition reaction. The present methodologie...

Full description

Saved in:
Bibliographic Details
Published in:Russian journal of general chemistry 2019-12, Vol.89 (12), p.2562-2570
Main Authors: Jassem, A. M., Al-Ajely, H. M., Almashal, F. A. K., Chen, B.
Format: Article
Language:English
Subjects:
Activated carbon
Biological activity
Carbonyl groups
Carbonyls
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Michael reaction
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Two efficient procedures have been developed for the synthesis of pyroglutamic acid analogues 28 , 29 , and 34 . According to the first method the Ugi (4C3C) reaction is followed by a post-transformation reaction, and the second method involves the Michael addition reaction. The present methodologies demonstrate the applicability of 1-(2,2-dimethoxyethyl)-2-isocyanobenzene ( 15 ) as a cleavable isocyanide in the Ugi/ post-transformation reaction and a strong nucleophile in the Michael addition reaction. The framework of pyroglutamic acid analogues has been constructed by the selective cleavage of the C -terminal amide bond and nucleophilic addition to the activated α,β-unsaturated carbonyl group.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363219120363