Synthesis of pharmacophores containing a prolinate core using a multicomponent 1,3-dipolar cycloaddition of azomethine ylides

A multicomponent 1,3-dipolar cycloaddition between heterocyclic aldehydes, amino esters and dipolarophiles is efficiently promoted by silver acetate as catalyst, and depending on the nature of the heterocycle and its reactivity the reaction requires 70 °C or rt to complete. Selected pharmacophores a...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2017-12, Vol.73 (49), p.6840-6846
Main Authors: Selva, Elisabet, Castelló, Luis M., Mancebo-Aracil, Juan, Selva, Verónica, Nájera, Carmen, Foubelo, Francisco, Sansano, José M.
Format: Article
Language:English
Subjects:
Azanucleoside
Azomethine ylides
Cycloaddition
Multicomponent
Prolinates
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:A multicomponent 1,3-dipolar cycloaddition between heterocyclic aldehydes, amino esters and dipolarophiles is efficiently promoted by silver acetate as catalyst, and depending on the nature of the heterocycle and its reactivity the reaction requires 70 °C or rt to complete. Selected pharmacophores anchored to a formyl group are chromone, 5-methoxyindole, pyridoxal surrogates and a very attractive uracyl derivative. The preference of each tested amino esters towards different dipolarophiles is discussed. At the end, a selective reduction of the ester group allows to obtain a very interesting dideoxiazanucleoside derivative. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.10.030