Synthesis of 1-Amino-3-oxo-2,7-naphthyridines Smiles Rearrangement: A New Approach in the Field of Chemistry of Heterocyclic Compounds

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2022 Jun 10

PMID 35682584

Authors

Samvel N Sirakanyan

Domenico Spinelli

Athina Geronikaki

Luca Zuppiroli

Riccardo Zuppiroli

Victor G Kartsev

Elmira K Hakobyan

Hasmik A Yegoryan

Anush A Hovakimyan

Affiliations

Soon will be listed here.

Abstract

In this paper we describe an efficient method for the synthesis of new heterocyclic systems: furo[2,3-]-2,7-naphthyridines , as well as a new method for the preparation of 1,3-diamino-2,7-naphthyridines . For the first time, a Smiles rearrangement was carried out in the 2,7-naphthyridine series, thus gaining the opportunity to synthesize 1-amino-3-oxo-2,7-naphthyridines , which are the starting compounds for obtaining furo[2,3-]-2,7-naphthyridines. The cyclization of alkoxyacetamides proceeds via two different processes: the expected formation of furo[2,3-]-2,7-naphthyridines and the 'unexpected' formation of 1,3-diamino-2,7-naphthyridines ( a Smiles type rearrangement).

Citing Articles

Synthesis and Rearrangement of New 1,3-Diamino-2,7-naphthyridines and 1-Amino-3-oxo-2,7-naphthyridines.

Sirakanyan S, Spinelli D, Mattioli E, Calvaresi M, Geronikaki A, Kartsev V Int J Mol Sci. 2024; 25(22).

PMID: 39596048 PMC: 11593454. DOI: 10.3390/ijms252211977.

New Bicyclic Pyridine-Based Hybrids Linked to the 1,2,3-Triazole Unit: Synthesis via Click Reaction and Evaluation of Neurotropic Activity and Molecular Docking.

Sirakanyan S, Spinelli D, Petrou A, Geronikaki A, Kartsev V, Hakobyan E Molecules. 2023; 28(3).

PMID: 36770592 PMC: 9920413. DOI: 10.3390/molecules28030921.

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