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

• Published in: International journal of molecular sciences Vol. 25; no. 22; p. 11977
• Main Authors: Sirakanyan, Samvel N., Spinelli, Domenico, Mattioli, Edoardo Jun, Calvaresi, Matteo, Geronikaki, Athina, Kartsev, Victor G., Hakobyan, Elmira K., Yegoryan, Hasmik A., Jughetsyan, Hasmik V., Manukyan, Mariam E., Hovakimyan, Anush A.
• Format: Journal Article
• Language: English
• Published: 07-11-2024
• ISSN: 1422-0067; 1422-0067
• DOI: 10.3390/ijms252211977

Herein we describe the synthesis and rearrangement of 1,3-diamino-2,7-naphthyridines and 1-amino-3-oxo-2,7-naphthyridines. In the case of 1,3-diamino-2,7-naphthyridines, it was found that the rearrangement reaction was influenced by both the substituent at the 7th position of the 2,7-naphthyridine ring and by the nature of the cyclic amine at the 1st position. The influence was mainly steric. The reaction of 1-amino-3-oxo-2,7-naphthyridines with amines was studied for the first time. It was revealed that for these substrates, the rearrangement occurs faster and without any influence of the alkyl and cyclic amine groups. We also observed the nucleophilic addition of the amine to the carbonyl group of the rearranged product with the formation of a Schiff base. The calculation of the ESP charges on these substrates indicates a considerable increase in the positive charge on the cyano group that suffers the nucleophilic attack during the rearrangement process, possibly explaining its increased tendency to react and to have a higher reaction velocity.