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

• Published in: International journal of molecular sciences Vol. 23; no. 11; p. 5904
• Main Authors: Sirakanyan, Samvel N, Spinelli, Domenico, Geronikaki, Athina, Zuppiroli, Luca, Zuppiroli, Riccardo, Kartsev, Victor G, Hakobyan, Elmira K, Yegoryan, Hasmik A, Hovakimyan, Anush A
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 25-05-2022; MDPI
• Subjects: 1,3-diamino-2,7-naphthyridines; 1-amino-3-oxo-2,7-naphthyridines; alkylation; Biological activity; cyclization; furo[2,3-c]-2,7-naphthyridines; Heterocyclic compounds; Smiles rearrangement; Sodium; United States > US; Smiles rearrangement; alkylation; 1,3-diamino-2,7-naphthyridines; cyclization; furo[2,3-c]-2,7-naphthyridines; 1-amino-3-oxo-2,7-naphthyridines
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms23115904

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).