The short route to chalcogenurea-substituted 3,6-epoxyisoindoles an intramolecular Diels-Alder furan (IMDAF) reaction. Antibacterial and antifungal activity

N -Furfuryl allylamines react with a broad range of isocyanates, isothiocyanates, isoselenocyanates with the formation of a 3 a ,6-epoxyisoindole core in one synthetic stage. The interaction sequence involves two consecutive steps: the nucleophilic addition reaction and the intramolecular Diels-Alde...

Full description

Saved in:
Bibliographic Details
Published in:New journal of chemistry 2024-07, Vol.48 (29), p.12947-12959
Main Authors: Mertsalov, Dmitriy F, Shchevnikov, Dmitriy M, Lovtsevich, Lala V, Novikov, Roman A, Khrustalev, Victor N, Grigoriev, Mikhail S, Romanycheva, Anna A, Shetnev, Anton A, Bychkova, Olga P, Trenin, Alexey S, Zaytsev, Vladimir P
Format: Article
Language:
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:N -Furfuryl allylamines react with a broad range of isocyanates, isothiocyanates, isoselenocyanates with the formation of a 3 a ,6-epoxyisoindole core in one synthetic stage. The interaction sequence involves two consecutive steps: the nucleophilic addition reaction and the intramolecular Diels-Alder furane (IMDAF) reaction. The scope and limitations of the proposed method were thoroughly investigated, and it was revealed that the key [4+2] cycloaddition step proceeds through an exo -transition state, giving rise to the exclusive formation of a single diastereomer of the target heterocycle. Dynamic temperature NMR analysis allowed to fully investigating a case of coalescence of NMR signals and determined the coalescence temperature during the transition O → Se. The antimicrobial properties of the obtained compounds against sensitive strains of yeast Candida albicans , fungus Aspergillus niger and bacteria including Staphylococcus aureus , Micrococcus luteus , Pseudomonas fluorescens were identified. A concise preparative IMDAF strategy for the synthesis of chalcogenurea-substituted 3 a ,6-epoxyisoindoles, which display antifungal and antibacterial activity, starting from readily available materials was proposed.
ISSN:1144-0546
1369-9261
DOI:10.1039/d4nj01174k