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Article

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

by
Samvel N. Sirakanyan
1,*,
Domenico Spinelli
2,
Edoardo Jun Mattioli
2,
Matteo Calvaresi
2,
Athina Geronikaki
3,
Victor G. Kartsev
4,
Elmira K. Hakobyan
1,*,
Hasmik A. Yegoryan
1,
Hasmik V. Jughetsyan
1,
Mariam E. Manukyan
1 and
Anush A. Hovakimyan
1
1
Institute of Fine Organic Chemistry of A. L. Mnjoyan, Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Science of Republic of Armenia, Ave. Azatutyan 26, Yerevan 0014, Armenia
2
Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum-Università di Bologna, Via F. Selmi 2, 40126 Bologna, Italy
3
School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece
4
InterBioScreen Ltd., 119019 Moscow, Russia
*
Authors to whom correspondence should be addressed.
Int. J. Mol. Sci. 2024, 25(22), 11977; https://doi.org/10.3390/ijms252211977
Submission received: 14 October 2024 / Revised: 1 November 2024 / Accepted: 5 November 2024 / Published: 7 November 2024
(This article belongs to the Special Issue Organic/Inorganic Nanocomposites on the Basis of 'Three Pillars' (Organic Compounds, Metal Nanoparticles, and Carbon Nanomaterials))
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Abstract

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.
Keywords: 2,7-naphthyridine derivatives; nucleophilic aromatic substitution (SNAr); rearrangement reactions; Smiles rearrangement; NMR; Schiff bases; ESP charges 2,7-naphthyridine derivatives; nucleophilic aromatic substitution (SNAr); rearrangement reactions; Smiles rearrangement; NMR; Schiff bases; ESP charges

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MDPI and ACS Style

Sirakanyan, S.N.; Spinelli, D.; Mattioli, E.J.; Calvaresi, M.; Geronikaki, A.; Kartsev, V.G.; Hakobyan, E.K.; Yegoryan, H.A.; Jughetsyan, H.V.; Manukyan, M.E.; et al. Synthesis and Rearrangement of New 1,3-Diamino-2,7-naphthyridines and 1-Amino-3-oxo-2,7-naphthyridines. Int. J. Mol. Sci. 2024, 25, 11977. https://doi.org/10.3390/ijms252211977

AMA Style

Sirakanyan SN, Spinelli D, Mattioli EJ, Calvaresi M, Geronikaki A, Kartsev VG, Hakobyan EK, Yegoryan HA, Jughetsyan HV, Manukyan ME, et al. Synthesis and Rearrangement of New 1,3-Diamino-2,7-naphthyridines and 1-Amino-3-oxo-2,7-naphthyridines. International Journal of Molecular Sciences. 2024; 25(22):11977. https://doi.org/10.3390/ijms252211977

Chicago/Turabian Style

Sirakanyan, Samvel N., Domenico Spinelli, Edoardo Jun Mattioli, Matteo Calvaresi, Athina Geronikaki, Victor G. Kartsev, Elmira K. Hakobyan, Hasmik A. Yegoryan, Hasmik V. Jughetsyan, Mariam E. Manukyan, and et al. 2024. "Synthesis and Rearrangement of New 1,3-Diamino-2,7-naphthyridines and 1-Amino-3-oxo-2,7-naphthyridines" International Journal of Molecular Sciences 25, no. 22: 11977. https://doi.org/10.3390/ijms252211977

APA Style

Sirakanyan, S. N., Spinelli, D., Mattioli, E. J., Calvaresi, M., Geronikaki, A., Kartsev, V. G., Hakobyan, E. K., Yegoryan, H. A., Jughetsyan, H. V., Manukyan, M. E., & Hovakimyan, A. A. (2024). Synthesis and Rearrangement of New 1,3-Diamino-2,7-naphthyridines and 1-Amino-3-oxo-2,7-naphthyridines. International Journal of Molecular Sciences, 25(22), 11977. https://doi.org/10.3390/ijms252211977

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